Highland Woods

Updated July 2026 · By McGreevy and Comisar, Domain Realty

Highland Woods Golf & Country Club is an established, member-owned bundled equity-golf community of 799 residences in Bonita Springs, Florida, wrapped around an 18-hole Gordon Lewis championship course just off Tamiami Trail (US-41). Built out in the late 1990s and turned over to its members in 2002, Highland Woods stands apart from newer golf communities on two counts that matter to buyers: every single home comes with a full equity golf membership and immediate tee times with no waitlist, and the community carries no Community Development District (CDD) bond debt on top of ordinary Lee County property taxes. If you are buying or selling in Highland Woods, McGreevy and Comisar is the team that knows this community, its fee structure, and its neighborhoods down to the estoppel line.

We are the #1 real estate team in Southwest Florida since 2012 and Top 1% nationally since 2008, with over $2.5 billion in real estate sold and $900 million in personal sales between Jesse McGreevy and Marc Comisar. Our office sits at 24031 S. Tamiami Trail, Suite 101, in Bonita Springs, minutes from the Highland Woods gatehouse. This page is the definitive, primary-sourced guide to Highland Woods: the club and its bundled equity membership, the golf, the amenities, every neighborhood, the current market, governance, and the true cost of ownership. When a live market figure belongs, we pull it fresh from the MLS right before publishing so the numbers you read are current.

Whether you want a free valuation of your Highland Woods home or a private tour of what is for sale, call Jesse McGreevy direct at (239) 898-6072 or Marc Comisar at (239) 287-5873. McGreevy and Comisar are part of Domain Realty.

Why McGreevy and Comisar Are the Best Realtor for Highland Woods

If you're searching for the best realtor for Highland Woods, whether you're ready to sell your Highland Woods home or buy your next one, McGreevy and Comisar is the team that delivers. We are the #1 real estate team in Southwest Florida since 2012, Top 1% Real Estate Agents Nationally Since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse and Marc.

Recent Highland Woods track record (last 12 months): 36 homes sold · $17.4 million in dollar volume · 88 days average time to contract · 94.0 percent average sale-to-list ratio · highest-priced sold $1,100,000 · fastest sold the same day it listed.

Honors and recognition:

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 20 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and Team have sold over 2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

Selling your Highland Woods home? Get a free home valuation at https://mcgreevyandcomisar.com/home-valuation or call Jesse direct at (239) 898-6072. We are a top-reviewed Highland Woods real estate team, and you can read what clients say on our Google reviews before you ever pick up the phone.

Buying a home in Highland Woods? Call Marc at (239) 287-5873 for a personalized buyer consultation.

Highland Woods at a Glance

Highland Woods Golf & Country Club is a 799-residence bundled equity-golf community at 9100 Highland Woods Blvd, Bonita Springs, Lee County, FL 34135, off US-41 just north of West Terry Street. It was master-planned by the Bonita Bay Group, built by U.S. Home Corporation, and opened in 1995. Every home carries one mandatory Owner Equity golf membership, and the community has no CDD. Here are the key facts at a glance.

Sources: Highland Woods Golf & Country Club (hwgcc.com); Highland Woods 2026 Master Association Schedule of Fees; Lee County Property Appraiser; Lee County Tax Collector; recorded Declaration of Covenants, Conditions and Restrictions (OR Book 2612, Pages 3397-3485); sunbiz.org (N95000000818).

Table of Contents

Use this table of contents to jump to any section of our Highland Woods guide. The page covers the community, the club and its bundled equity golf membership, the golf course, amenities, homes and neighborhoods, the current market, governance and cost of ownership, location and lifestyle, schools and healthcare, hurricanes and flood zones, what is coming nearby, renting and investing, selling with the #1 team, and full buyer and seller FAQs.

• Why McGreevy and Comisar Are the Best Realtor for Highland Woods
• Highland Woods at a Glance
• Table of Contents
• Overview: What Makes Highland Woods Distinct
• The Bundled Equity Golf Membership Explained
• The Golf Course at Highland Woods
• The Clubhouse and Dining at Highland Woods
• Amenities: Racquet Sports, Bocce, Pickleball, Fitness and Pools
• Homes and Real Estate in Highland Woods
• The Neighborhoods of Highland Woods
• Current Market Snapshot for Highland Woods
• HOA, Governance and Fees at Highland Woods
• What It Costs to Own in Highland Woods
• Location and Lifestyle in Highland Woods
• Schools for Highland Woods
• Healthcare Near Highland Woods
• Hurricane, Flood Zones and Insurance in Highland Woods
• What's Coming Near Highland Woods
• Renting and Investing in Highland Woods
• Thinking of Selling Your Highland Woods Home? List With the #1 Team in Southwest Florida Since 2012
• Why McGreevy and Comisar
• Frequently Asked Questions: Buying in Highland Woods
• Frequently Asked Questions: Selling in Highland Woods
• Downloadable Documents and Public Records
• Sources
• Key Takeaways

Overview: What Makes Highland Woods Distinct

Highland Woods is distinct because it pairs a true bundled equity golf membership with an established, fully built-out setting and no CDD. Every one of the 799 homes carries a full golf membership with no waitlist, so buyers golf from day one. Because the community was developer and member funded in the 1990s rather than CDD-bond financed, there is no district bond debt layered onto Lee County property taxes.

Southwest Florida has dozens of golf communities, and on the surface many look alike: a gatehouse, a Gordon Lewis or Arthur Hills course, coach homes and villas, a clubhouse with pickleball. What separates them is the membership model, the age and financial maturity of the community, and the tax structure. Highland Woods sits in a favorable position on all three.

A true bundled equity club, not a tiered one. Highland Woods has exactly one membership category, "Owner Equity Members," and it is mandatory and tied to the deed. The club's own documents state it plainly: "This is a bundled club. Every Owner of title to a Lot or Living Unit within the Community is a Member of the Club" (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com), and the Rules and Regulations confirm "There is one type of membership: Owner Equity Members" (Rules and Regulations v1.10, hwgcc.com). There is no separate Golf-versus-Social split, no initiation-driven equity certificate you buy and later sell, and no golf waitlist. When you close on any home in Highland Woods, from the smallest Heathermoor condo to the largest Summer Greens single-family home, you become a full golf member. This is a meaningful contrast with non-bundled equity clubs, where golf access can carry a multi-year waitlist and a separate five- or six-figure initiation deposit. At Highland Woods, membership is baked into the purchase.

Established and fully built out. Highland Woods is not a work in progress. The community has a documented pedigree: the land was master-planned, platted, and declared by the Bonita Bay Limited Partnership, the same Bonita Bay Group (David Lucas's development company) behind Bonita Bay, Pelican Landing, and The Colony, with the recorded master Declaration executed on June 26, 1995 (Lee County Official Records Book 2612, Pages 3397-3485). The homes were then built and sold by U.S. Home Corporation, named as the "Developer" in that same recorded Declaration, a national homebuilder that Lennar acquired in 2000 (Declaration OR 2612/3398; Lennar investor relations, "In 2000, we acquired U.S. Home Corporation"). The 18-hole Gordon Lewis course opened in 1995, the residential villages built out through roughly 2000 in recorded phases (Phase One plat approved by the Lee County Commission on 05/17/1995; Phase Three recorded 06/02/1997), and the developer completed turnover of the club to the membership by 2002, when the Articles were restated by member vote and the developer-control language was removed (sunbiz N95000000818, Amended and Restated Articles filed 07/08/2002). That maturity matters. The community is resident-governed, the amenities have already been built and then reinvested in twice (a roughly $6.5 million clubhouse and course program completed in 2016 and a roughly $8.3 million "Project '22" amenity build-out), and the streetscape is grown-in with mature landscaping rather than raw and unfinished. Buyers are stepping into a settled community with a known cost structure and a clear paper trail, not betting on a developer's promises.

No CDD. This is one of the quiet financial advantages of an older Bonita Springs golf community, and it is provable. We pulled an actual 2025 Lee County Tax Collector bill for a Highland Woods single-family parcel (STRAP 27-47-25-B1-0170L.0030) and read the full list of taxing authorities: Lee County, the public schools, the City of Bonita Springs, the library, South Florida Water Management, the Bonita Springs Fire District, and the usual mosquito and navigation districts. There is no CDD line and no non-ad-valorem CDD assessment (Lee County Tax Collector, parcel 27-47-25-B1-0170L.0030, 2025 bill). Many newer Southwest Florida golf communities carry a Community Development District bond that adds a fixed annual assessment, often thousands of dollars, on top of property taxes for 20 to 30 years to repay infrastructure bonds. Highland Woods has none. Your tax bill is ordinary Lee County ad-valorem millage, and your community carrying cost is the club dues plus your neighborhood association fee, with no CDD bond stacked on top.

A community built for full-time and seasonal residents alike. Highland Woods is primarily an owner-occupant and seasonal community with a genuine social calendar: game nights, tournaments, dinner dances, water aerobics six days a week, and an active racquet-sports scene. It permits leasing with a 30-day minimum for owners who want flexibility, but it is not an investor-churn community. That balance, real amenities and an engaged membership without a transient feel, is part of why the community holds its identity so well.

For buyers, the distinct combination is simple to state: immediate equity golf, a mature and financially transparent club, and no CDD. For sellers, those same three facts are your strongest talking points, and McGreevy and Comisar know how to put them in front of the right buyer. Call Jesse at (239) 898-6072 or Marc at (239) 287-5873 to talk through how these advantages translate into your specific home's value.

The Bundled Equity Golf Membership Explained

Every Highland Woods home carries one mandatory Owner Equity golf membership that conveys at closing with no waitlist. For 2026, annual club dues are $13,812.79, and the buyer pays a one-time resale capital contribution of $10,000 at closing plus a $500 annual Food and Beverage minimum. There is one membership type, capped at the community's 799 units, so golf is immediate from day one (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com).

This is the single most important section on the page, because the bundled equity membership is what you are actually buying at Highland Woods, alongside the real estate. Understand it fully and the rest of the community makes sense. Every number below comes from the club's own recorded fee schedules and Rules and Regulations; nothing here is estimated.

One membership type: Owner Equity Members

Highland Woods is a member-owned equity club with a single class of membership. The club corporation, Highland Woods Golf & Country Club, Inc. (a Florida not-for-profit, sunbiz N95000000818, filed 02/20/1995), is collectively owned and governed by its members through a Board of Trustees. There is no Golf membership, no Social membership, no Sports membership, and no separate tier: "There is one type of membership: Owner Equity Members. Owner Equity Members and their guest are entitled to use all of the Club's facilities" (Rules and Regulations v1.10, hwgcc.com). Because the membership right runs with the deeded home and every one of the 799 residences carries it, membership is inherently capped at the community's unit count. You cannot own in Highland Woods without being a full member, and you cannot be shut out of golf by a waitlist. The community's fixed 799-unit size is the membership cap.

Immediate golf, no waitlist

The practical payoff of the bundled model is immediacy. Because golf membership is bundled with ownership, a buyer becomes a full golf member at closing and can tee off from day one with no golf waitlist (hwgcc.com). At non-bundled equity clubs elsewhere in Southwest Florida, golf can carry a waitlist that runs from months to years, and a substantial refundable or non-refundable initiation deposit on top of the home price. Highland Woods eliminates both the wait and the separate initiation buy-in. This is the club's headline differentiator, and it is one of the first things a well-informed buyer asks about.

The 2026 money facts

Here is exactly what ownership at Highland Woods costs at the club level for 2026, straight from the club's Master Association Schedule of Fees.

Annual club dues for 2026: $13,812.79. These community-wide dues are billed by October 31 and due on or before January 1. They break down into five line items:

Source: Highland Woods 2025 and 2026 Master Association Schedule of Fees, hwgcc.com.

Total dues rose about 28% from 2025 to 2026. The two biggest movers were the Operating and Maintenance Fund and, notably, the Replacement Reserve Fund, which more than doubled from $950 to $2,500. That reserve increase is a healthy sign, not a red flag: it reflects a member-owned club deliberately building its capital reserves after a decade of major reinvestment, so that future amenity and course projects are funded from savings rather than surprise special assessments. Because the Board of Trustees resets these dues annually, the exact figure changes each year; the $13,812.79 shown here is the current 2026 number, and we confirm the live figure with the club before any closing.

One-time resale capital contribution for 2026: $10,000, paid by the buyer at closing. This is the equity buy-in every new owner pays into the club. The club describes it precisely: "This is a one-time charge to be collected at closing from the Buyer on a separate check. The Capital Contribution amount is reviewed and established by the Board of Trustees annually and will be determined by the date of closing" (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com). It was $6,500 in 2025 and $10,000 for 2026, so like the dues, it is a moving target set each year by the Board. The important points for a buyer: it is a one-time cost, not annual; it is paid by the buyer (not the seller); it is paid at closing on a separate check payable to Highland Woods Golf & Country Club; and you should budget the current-year figure, which we verify with the club before closing.

Food and Beverage minimum: $500 per year. Each membership carries a $500 annual minimum spend in the club's dining venues. Any unused balance is used by December 31 and, on a mid-year resale, the buyer assumes the seller's remaining unspent F and B balance for that year (the annual New Year's Eve event is excluded) (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com). For most owners who use the Grille Room and the poolside Woods Café through the season, the $500 minimum is spent well before year end.

Estoppel fee: $250 to $450. At resale, the club charges an estoppel fee of $250 to $450, required at closing on a separate check, with a $100 charge for updates and a $100 charge to expedite (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com). The estoppel is the club's official statement of what is owed on a specific unit at closing, and it is a normal, expected line in any Highland Woods transaction.

How the membership conveys at closing

The conveyance mechanics are simple and fast. After closing, the buyer's Warranty Deed together with the required fees (the capital contribution and estoppel, on separate checks payable to Highland Woods Golf & Country Club) are forwarded to the Highland Woods Admin Office at 9100 Highland Woods Blvd. The club then activates the membership to the new owner within 24 to 48 hours of receiving the deed and fees (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com). There is no separate membership application to be approved, no interview, and no waitlist: the membership is an attribute of the home, so transferring the deed transfers the membership. A capable listing or buyer agent coordinates the deed and the separate checks so that a new owner is teeing off within days of closing.

The two different "transfer" concepts (do not confuse them)

Highland Woods uses the word "transfer" in two different situations, and buyers sometimes conflate them:

1. At a home sale (resale): the buyer's cost to take over the equity membership is the one-time resale capital contribution ($10,000 for 2026) plus the estoppel fee ($250 to $450), both paid by the buyer at closing. That is the true membership buy-in at a purchase. There is no additional separately named "resale membership transfer fee" beyond the capital contribution and estoppel in the club's recorded schedule (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com).
2. For renters (an owner transferring amenity privileges to a tenant): a distinct "Transfer of Membership Fee" applies. An owner who leases the home may transfer amenity privileges to the tenant for a minimum 30-day period, and that Transfer of Membership Fee is tiered by the length of the stay and is payable to the Master Association (hwgcc.com Real Estate page; Rules and Regulations v1.10). During a transfer, the owner's own club privileges are suspended, and an owner may transfer privileges a maximum of 12 times per year, only when the account is current. The exact dollar tiers of this tenant transfer fee are held at the Admin Office and are not published on the club's public site, so we do not quote a number here; contact the club or your agent for the current schedule.

The short version: a buyer purchasing a home pays the $10,000 capital contribution plus the estoppel at closing; a landlord leasing a home pays the tiered tenant transfer fee when handing amenity access to a renter; and the seller's unused Food and Beverage balance carries over to the buyer.

What this means for value

The bundled equity membership shapes value in a way that surprises buyers who are new to Southwest Florida golf communities. Because every home pays the same master club dues and the same capital contribution regardless of price tier, the club-level carrying cost is roughly flat across a $200,000 Heathermoor condo and an $800,000 Summer Greens home. The real estate price differs by product; the golf membership does not. That flat membership cost is exactly why Highland Woods condos can be one of the most affordable ways in all of Bonita Springs to own a full, immediate, no-waitlist golf membership: you get the identical club and the identical course whether you buy the entry condo or the premium home. For sellers, it means your buyer pool includes value-focused golfers who want the membership without the single-family price. McGreevy and Comisar position each Highland Woods listing to exactly the buyer who values what that specific home and its bundled membership deliver. To talk through the membership math for a specific home, call Jesse at (239) 898-6072 or Marc at (239) 287-5873.

The Golf Course at Highland Woods

The Highland Woods golf course is a private, member-owned 18-hole, par-72 championship layout designed and built by noted Southwest Florida architect Gordon Lewis, opened in 1995. Playing to roughly 6,799 yards from the tips on the current scorecard and down to about 3,373 yards from the forward tees, it uses xeric design principles to work with the natural terrain, threading through preserves, waterways, and a protected gopher tortoise habitat (Rules and Regulations v1.10 and 2025 Scorecard, hwgcc.com).

Golf is the heart of Highland Woods, and it is genuinely good golf: not a token executive nine tacked onto a housing tract, but a full championship course that a serious golfer can play year-round and a newer player can grow into.

Design and character

Gordon Lewis is one of the region's most recognized golf architects, and Highland Woods is one of his mid-1990s Bonita Springs works. The club describes it as "a private member owned 18-hole, (par 72) championship golf course designed and built by the noted architect Gordon Lewis," and notes that "Mr. Lewis used xeric principles to preserve the integrity of the natural terrain" (Rules and Regulations v1.10, hwgcc.com; the course build year of 1995 is corroborated by the Gordon G. Lewis architect record on GolfPass). Xeric design means the course was routed and planted to respect the site's native drainage, uplands, and vegetation rather than bulldozing them, which is why Highland Woods plays through mature preserves and lakes rather than a flat, featureless field. The routing incorporates natural water-management lakes and conservation tracts, and holes 12 and 13 border a state-protected gopher tortoise "No Hunt" preserve where entry is prohibited (Rules and Regulations v1.10, hwgcc.com). That preserve is part of the community's environmental fabric and a genuine amenity for residents who value wildlife and green space.

Yardage and tees

The current 2025 scorecard shows a par-72 course with nine tee sets, ranging from about 6,799 yards at the tips down to roughly 3,373 yards from the most forward markers, so every level of player has a comfortable set of tees.

Source: Highland Woods 2025 Scorecard, hwgcc.com. Front nine par 36, back nine par 36. Older club Rules and Regulations list a longer Black-tee figure from a prior measurement; the current scorecard above is authoritative.

The front nine from the tips totals 3,464 yards and includes par-5s at holes 6 (518 yards) and 8 (539 yards), with a mix of demanding par-4s and shorter par-3s. The nine-tee spread is a real asset for a bundled community, where members range from low-handicap regulars to social players and grandchildren visiting in season: everyone finds a set that fits, and the course stays enjoyable rather than punishing.

Practice facilities

Highland Woods backs its championship course with a full practice complex, not an afterthought range. Members have access to a 50,000-square-foot aqua driving range tee with an additional mat hitting area, a 7,000-square-foot putting green, and an 11,400-square-foot chipping and putting practice area featuring three bunkers, plus a short-game area and on-course comfort and water stations (Golf Information page and Rules and Regulations v1.10, hwgcc.com). That is enough short-game and range space to actually get better, which matters to golfers who are choosing a club they will play several times a week.

Golf operations

Tee times are booked up to seven days out through the Chelsea Tee Time Reservation System, which uses a rolling play-history fairness algorithm so that access stays equitable across the membership rather than being dominated by whoever calls first (Rules and Regulations v1.10, hwgcc.com). This is an important detail in a bundled community: because every one of the 799 homes is a full golf member, a fair tee-time system is what keeps the course playable for everyone. The course opens around 7:20 AM and plays to dark, under USGA rules, with handicap-posting computers at the Golf Shop and outside the Grille Room, plus Men's Day and Ladies' Day programming and an active roster of member tournaments through the season. Private or personally leased golf carts are not permitted on club property except for documented temporary medical necessity with Board approval, so the cart fleet is uniform and club-managed. The club reports roughly 40,000 rounds a year, which reflects an engaged golfing membership rather than an underused course (club General Manager profile, 2024). Golf staff assignments are time-sensitive and change periodically; the club's Golf Shop is reachable at (239) 498-0553 for current tee-time and professional-staff information.

The 19th Hole and course reinvestment

The course has been maintained and reinvested in, not left to age. As part of the roughly $6.5 million clubhouse and course program completed in 2016, the club funded a roughly $1.6 million golf course renovation that included a wall-to-wall re-grassing and greens replacement (Our Club page, hwgcc.com). That kind of periodic re-grassing is exactly what keeps a 1990s course playing like a modern one. For buyers, a member-owned course with a documented reinvestment history and a healthy replacement reserve is a strong signal that the golf, the reason many people buy here, will stay in top condition. To arrange a look at the course and clubhouse as part of a home tour, call Marc at (239) 287-5873.

The Clubhouse and Dining at Highland Woods

The Highland Woods clubhouse offers three distinct dining venues: the casual Grille Room overlooking the 18th green, a formal Dining Room for fine-dining nights and buffets, and the poolside Woods Café added in the "Project '22" renovation. Together with an active social calendar of game nights, dinner dances, and seasonal events, dining is a genuine hub of daily life at Highland Woods, backed by the $500 annual Food and Beverage minimum (Our Club, Grille Room, Dining Room and Woods Café pages, hwgcc.com).

A club is only as good as the room where members actually gather, and Highland Woods invested heavily in exactly those rooms. The clubhouse has been through two major reinvestment programs in the last decade. The 2016 program (roughly $6.5 million in total) delivered a new two-story cart barn with the upper-level 24-hour fitness facility, a full clubhouse interior renovation including a new and larger Grille Room kitchen, and new restroom facilities for the bocce and practice areas, alongside the roughly $1.6 million wall-to-wall course re-grassing (Our Club page, hwgcc.com). Then the roughly $8.3 million "Project '22" program added the resort-style pool, the poolside Woods Café, six pickleball courts, resurfaced tennis, and a new golf shop (Our Club page, hwgcc.com). For a buyer, two multi-million-dollar reinvestment cycles inside ten years signal a member-owned club that funds and maintains its facilities rather than letting them age, and it is exactly why the rising Replacement Reserve line in the dues is a feature, not a warning.

The Grille Room

The Grille Room is the everyday heart of the club: a relaxed, "casual yet sophisticated" room serving casual-to-upscale American fare with panoramic views of the 18th green and large-screen TVs, with a menu refreshed regularly for seasonal specialties (Grille Room page, hwgcc.com). Proper golf attire is permitted, so members roll straight off the course into lunch. This is where the daily rhythm of the club happens, after a round, before a card game, or over a casual dinner.

The formal Dining Room

For a more elevated evening, the formal Dining Room overlooks the grounds and the aqua driving range and hosts the club's marquee social events: fine-dining dinner nights, seafood and prime rib buffets, and dinner-dance parties including the Welcome Back party, New Year's Eve, Valentine's Day, and End of Season celebrations (Dining Room page and Rules and Regulations v1.10, hwgcc.com). The Dining Room also anchors the club's recurring member events, including Tuesday Game Nights (bingo and trivia) and a Sunday breakfast buffet. After 5:00 PM the Main Dining Room moves to Evening Country Club Casual dress (gentlemen in long pants). This is the room that makes Highland Woods feel like a country club rather than just a golf course, and its calendar is a big part of why members describe the community as social and welcoming.

The Woods Café (poolside)

The newest venue, delivered by the roughly $8.3 million "Project '22" renovation, is the Woods Café, an indoor and outdoor café at the resort-style pool serving fresh meals and handcrafted cocktails, with Happy Hour and casual poolside dining (Woods Pool Café page, hwgcc.com). The café turned the pool deck into a true social destination and gave members a relaxed, in-season gathering spot beyond the formal dining rooms.

Dining as part of ownership

Because every membership carries a $500 annual Food and Beverage minimum, dining is woven into ownership rather than being an occasional extra (Highland Woods 2026 Master Association Schedule of Fees, hwgcc.com). In practice, most active members spend the minimum easily across the season between the Grille Room, the Dining Room's event nights, and the Woods Café. The three venues, plus the constant calendar of tournaments, game nights, and dinner dances, are why Highland Woods reads as an engaged, full-service club and not simply a place to play 18 holes. The Restaurant line is (239) 495-0500 for current dining hours and event reservations.

Amenities: Racquet Sports, Bocce, Pickleball, Fitness and Pools

Beyond golf, Highland Woods offers a deep amenity set: four lighted tennis courts on a cushioned Club 40 Advantage surface, six dedicated pickleball courts, a three-court Clay Tech bocce complex, a 24-hour two-level fitness center built in 2016, and seven heated pools including a resort-style zero-entry main pool with a Jacuzzi and the poolside Woods Café. Racquet sports and water aerobics run on active seasonal calendars, and courts and paddles are free to members (Racquet Sports, Bocce, Pools and Fitness pages, hwgcc.com).

The roughly $8.3 million "Project '22" renovation is what modernized this amenity set, adding the pickleball courts, resurfacing tennis, expanding the pool, and building the café. The result is a country club that keeps members active well beyond the first tee.

Tennis

Highland Woods has four tennis courts, lighted for night play, finished in a cushioned "Club 40 Advantage" surface that the club describes as gentle on the knees (Racquet Sports page, hwgcc.com). These are a hard cushioned surface, not Har-Tru clay. Tennis programming is robust: men's and women's doubles leagues, team practices, weekly drop-in sessions, a Saturday-morning Mixed Round Robin, and a full slate of social tennis events each fall and winter season, including the Annual Tennis Club Championship. A ball machine is available, and there is no charge to use the courts or the ball machine; daily hours run 8:00 AM to 10:00 PM (Racquet Sports page and Rules and Regulations v1.10, hwgcc.com).

Pickleball

Six dedicated pickleball courts were added in the "Project '22" build-out, and pickleball has become one of the community's most popular activities. Open play runs year-round from 8:00 AM to 6:00 PM, with dedicated Open Play each morning from 8:00 to 11:00, a practice ball machine available anytime, and paddles free to borrow from the Golf Pro Shop (Racquet Sports page, hwgcc.com). A Racquet Sports Committee hosts monthly pickleball and after-play socials from October through April, with interclub and intraclub league play, and Pickleball Ambassadors on hand for newcomers. For an active buyer, six dedicated courts (not lines painted on the tennis courts) is a meaningful differentiator.

Bocce

Highland Woods features a popular three-court bocce complex built with Clay Tech, a durable indoor-outdoor surface finished with light sand. Courtside amenities include shaded benches, restrooms, and a viewing patio with tables, chairs, and umbrellas, and the club runs seasonal six-week leagues for men, women, and couples; court time is reserved through the Admin Office and hours run 8:00 AM to 10:00 PM (Bocce page, hwgcc.com). (The club's December 2023 rulebook still references two bocce courts from before the expansion; the current amenity count is three.)

Fitness

The fitness center is a 24-hour facility built in 2016 on the second level of the two-story cart barn, overlooking the gardens and golf course. It comprises two 1,750-square-foot rooms: an equipment room for cross-training, stretching, and weights, plus a mirrored group-exercise studio. A certified personal trainer is available, and a wide array of classes is offered for all fitness levels (Fitness page and Our Club page, hwgcc.com). Twenty-four-hour access is a genuine convenience for residents who keep their own hours, and the on-site trainer and class schedule give the fitness center a following of its own.

Pools and spa

Highland Woods has seven heated common-area pools. The main pool at the clubhouse (approximately 63 by 32 feet) features a Jacuzzi/spa and the poolside Woods Café, and "Project '22" added a resort-style zero-entry pool. Six additional pools (approximately 40 by 20 feet) are located throughout the condominium and veranda neighborhoods, including one covered pool, and all pools are heated to roughly 84 degrees. Low-impact water aerobics classes run six days a week (Pools page and Rules and Regulations v1.10, hwgcc.com). Note that "spa" here refers to the Jacuzzi/hot tub at the main pool; Highland Woods does not operate a full treatment day-spa. The distribution of pools across the neighborhoods means most condo and veranda owners have a pool within a short walk of home, in addition to the resort pool at the clubhouse.

The gated setting and preserve

The community is guard-gated with a manned gatehouse and a 20 mph interior speed limit, and it wraps around the golf course, lakes, and the state-protected gopher tortoise preserve (Rules and Regulations v1.10, hwgcc.com). The Gatehouse line is (239) 498-2948. The combination of a staffed gate, mature landscaping, and preserved green space gives Highland Woods a quiet, secure, grown-in feel that newer communities take years to develop.

Taken together, the amenities make Highland Woods a full-lifestyle club rather than a golf-only address. For many buyers, the tennis, pickleball, bocce, fitness, and pools are what turn a house into a home base for an active Southwest Florida life. McGreevy and Comisar can walk you through every amenity on a private tour; call Jesse at (239) 898-6072 or Marc at (239) 287-5873.

Homes and Real Estate in Highland Woods

Highland Woods offers five product types across its 799 residences: entry-tier Heathermoor condos, mid-tier Terrace condos and St. Andrews Verandas coach homes, attached Highland Woods Villas, and premium single-family homes in the Summer Greens area. Resale prices span from the high-$100,000s for the smallest condos to roughly $800,000 and up for the largest single-family homes, all carrying the identical bundled equity golf membership (hwgcc.com Real Estate and For Sale pages; MLS resale data, verified live at publish).

Because the community was built out by U.S. Home Corporation across roughly 1996 to 2000 and is fully complete, everything here is resale, and there is a home for almost every buyer, from a first-time-in golfer looking for a lock-and-leave condo to a full-time resident wanting a pool home. The one constant across all of them is the equity membership.

The five product types

Heathermoor condos (entry tier). Two-bedroom, two-bath garden condos of roughly 1,042 to 1,106 square feet in three buildings along Highland Woods Boulevard, with detached carports and private storage and common elevators in the buildings. Heathermoor is the community's price-entry point and the most affordable way to own a full Highland Woods golf membership, with recent resale activity running from the high-$100,000s into the low-$300,000s (For Sale page, hwgcc.com; MLS resale data, verified live at publish).

Terrace condos (mid tier). Two-bedroom, two-bath low-rise condos of roughly 1,130 to 1,414 square feet across Terrace I through IV along Highland Woods Boulevard, with carport parking and common elevators. Terrace is a clean mid-tier condo with slightly larger floor plans than Heathermoor, typically transacting in the mid-$300,000s to mid-$400,000s (For Sale page, hwgcc.com; MLS resale data, verified live at publish).

St. Andrews Verandas (mid tier, largest product group). The Verandas are two-story veranda-style coach homes across St. Andrews Verandas I through VIII on Clarkston Drive and Sunderland Drive, offered in two- and three-bedroom plans of roughly 1,130 to 1,414 square feet with detached garages and open verandas; as two-story walk-ups, they do not have elevators. This is the single largest product group in Highland Woods, roughly 350 units, so it carries the deepest and most active resale inventory, with a broad price band spanning the community's entry-mid to upper-mid range (For Sale page, hwgcc.com; MLS resale data, verified live at publish).

Highland Woods Villas (mid to premium tier). Attached villas with a single-family feel on Clarkston Drive, offered as two-bedroom, two-bath plans of roughly 1,500 to 1,600 square feet with attached two-car garages and no shared elevator. The villas appeal to a buyer who wants a detached-home feel, their own garage, and no upstairs or downstairs neighbor, without stepping all the way up to a single-family price (For Sale page, hwgcc.com; MLS resale data, verified live at publish).

Single-family homes / Summer Greens (premium tier). Detached one-story homes in two-, three-, and four-bedroom plans of roughly 1,556 to 2,658 square feet, concentrated on Summer Greens Drive and nearby interior streets, many with private pools and spas and attached two-car garages. This is the premium tier of Highland Woods, generally transacting from the mid-$400,000s to roughly $800,000 and up for the largest pool homes (For Sale page, hwgcc.com; MLS resale data, verified live at publish).

The price-tier picture

General tiers reflect product and floor-plan differences. Live sold prices, active inventory, and price-per-square-foot are pulled from the MLS immediately before publish; see the Current Market Snapshot below.

For current pricing and availability, the market snapshot in the next section carries live MLS figures. In the last 12 months, Highland Woods recorded 36 sales, and there are currently 8 homes actively for sale across the five product types.

The U.S. Home product lineage

Highland Woods' floor plans have a recognizable heritage. The community was built by U.S. Home Corporation, which used the same Terraces, Verandas, Villas, and Single Family product taxonomy at its comparable Fort Myers bundled-golf community, Heritage Palms, a couple of years later (recorded Declaration OR 2612/3398 naming U.S. Home as Developer; Heritage Palms official club history). Buyers who have shopped other Southwest Florida bundled-golf communities from this era will find the layouts familiar and time-tested. These are proven 1990s-era plans: efficient, single-level living in the condos and villas, and straightforward one-story pool homes in the single-family tier. Because the plans repeat across buildings, comparable-sales analysis within a product type is clean, which helps both buyers and sellers arrive at an accurate value.

Choosing the right product for you

The right Highland Woods home depends on how you will use it. A seasonal buyer who wants to lock the door and fly north for the summer often favors an elevator-served Heathermoor or Terrace condo with minimal exterior maintenance. A buyer who wants a garage and no shared building but not a full single-family price gravitates to the St. Andrews Verandas coach homes or the Highland Woods Villas. A full-time resident or a buyer who wants a private pool steps up to the Summer Greens single-family homes. Because the golf membership is identical across all of them, the decision is genuinely about lifestyle and space rather than club access, and that is a refreshingly simple way to shop.

Why product knowledge matters here

The five product types at Highland Woods are not interchangeable, and pricing one correctly requires knowing the distinctions that a buyer will notice: which buildings have elevators, which Verandas associations have detached garages, which single-family streets back to the course versus a lake, and how the flat club dues change the value calculus at each tier. This is where a community specialist earns their keep. McGreevy and Comisar have sold across every tier in Southwest Florida's golf communities and know how to price, prepare, and market a Highland Woods home so it reaches the right buyer at the right number. Whether you own a Heathermoor condo or a Summer Greens pool home, call Jesse at (239) 898-6072 for a free, no-obligation valuation.

The Neighborhoods of Highland Woods

Highland Woods is organized into roughly 18 named neighborhood associations grouped under five marketing brands: Heathermoor (three condo associations), Terrace (four condo associations), St. Andrews Verandas (eight veranda associations), Highland Woods Villas (two villa associations), and the self-managed Single Family homes in the Summer Greens area. Each condominium neighborhood is its own Florida association with its own board, budget, and management company, all sitting under the master club (hwgcc.com Real Estate page; Florida DBPR Condominium Registry).

The neighborhood structure is worth understanding, because it determines your second layer of fees (the neighborhood association dues that sit on top of the master club dues) and it shapes the character of daily life, from whether your building has an elevator to which pool is closest to your door. Below is the full roster confirmed from the club's own management assignments and the Florida DBPR condominium registry.

The neighborhood roster

Sources: Highland Woods Golf & Country Club Real Estate page (management-company roster) and For Sale page; Florida DBPR Condominium Registry (Condo_CW.csv). Individual per-association unit counts are approximate pending a full Lee County parcel-roll pass.

The St. Andrews Verandas condominium associations were recorded from late 1995 through early 2000, the Terrace and Heathermoor associations from 1996 through 1998, tracking the community's build-out. Each is administered by its own property manager (Alliant, Compass Rose, Resort Management, Tropical Isles, NextGen, or Gulf Breeze, depending on the neighborhood), while the Single Family homes are self-managed under a resident president (Florida DBPR Condominium Registry; hwgcc.com Real Estate page). Note that a separate "Highland Woods Homeowners Association" registered in Tampa is unrelated to this Bonita Springs community and should not be confused with it.

The condominium associations in detail

For buyers who want to see the individual associations, the Florida DBPR condominium registry confirms each in-community condo association with its recorded date and approximate unit count. This is the kind of primary-source specificity that separates a real community guide from a generic listing page.

Source: Florida DBPR Condominium Registry (Condo_CW.csv). Unit counts are the registry figures; the Villas (Villas I and II) and the Summer Greens single-family homes are platted-lot product and are not recorded as condominium associations. Some St. Andrews Verandas associations show an administrative "Delinquent" reporting status in the state registry, which is a filing-status note and not a solvency judgment. We verify each neighborhood's current standing and dues at transaction time.

How the neighborhoods differ

• Heathermoor is the value entry: the smallest floor plans, the lowest prices, and elevator-served buildings, ideal for a lock-and-leave seasonal condo or a first purchase into the community.
• Terrace offers slightly larger condo floor plans with the same elevator convenience, a clean mid-tier choice for buyers who want a bit more space than Heathermoor without leaving the condo product.
• St. Andrews Verandas are the coach homes: two-story buildings with detached garages and open verandas, the largest and most-traded product group in the community, spanning a wide price band and offering both first-floor and second-floor units (the second-floor units are walk-ups, since the Verandas have no elevators).
• Highland Woods Villas deliver an attached single-family feel with a private attached two-car garage and no shared building, appealing to buyers who want a house-like experience at a villa price.
• Single Family (Summer Greens) is the premium tier: detached one-story homes, many with private pools, on the community's namesake single-family streets.

Dedicated neighborhood pages coming soon

Each of these neighborhoods deserves its own street-level guide, and dedicated Highland Woods neighborhood sub-pages are on the way. We are building individual pages for St. Andrews Verandas, the Terrace condos, Heathermoor, Highland Woods Villas, and the Summer Greens single-family homes, each with that neighborhood's specific association fee schedule, recent comparable sales, floor-plan detail, and street-level insight. Those pages will be linked here as they go live. In the meantime, for any neighborhood-specific question, including current association dues, recent comps, or which units are coming to market, call Jesse at (239) 898-6072 or Marc at (239) 287-5873. McGreevy and Comisar track inventory across all five product types in real time.

Current Market Snapshot for Highland Woods

The Highland Woods market covers five product types priced from the high-$100,000s for entry condos to roughly $800,000 and up for premium single-family homes, all carrying the same bundled equity golf membership. Recent snapshots have shown days on market running roughly in the 80-to-120-day range, but every live figure below (sold count, dollar volume, active listings, median price, price per square foot, and days on market) is pulled fresh from the MLS immediately before publish so the numbers are current.

Because Highland Woods is a fully built-out resale community with a mix of condos, villas, and single-family homes, its market moves differently at each tier. The condo tiers turn over more frequently and are more sensitive to seasonal demand; the single-family tier is thinner and more price-elastic. Here is the current picture.

Highland Woods market at a glance (last 12 months)

All figures pulled live from the MLS immediately before publish. Contact McGreevy and Comisar for the most current numbers and for tier-by-tier detail (condo versus villa versus single-family).

By product tier

For a more precise read, market performance splits by product type. Entry condos in Heathermoor, mid-tier condos in Terrace and the St. Andrews Verandas, the Highland Woods Villas, and the Summer Greens single-family homes each have their own recent sold ranges and absorption:

• Entry condos (Heathermoor): 3 closed sales in the last 12 months, $198,000 to $325,000
• Mid-tier condos (Terrace / St. Andrews Verandas): 21 closed sales in the last 12 months, $250,000 to $500,000
• Villas (Highland Woods Villas): 8 closed sales in the last 12 months, $457,000 to $687,500
• Single-family (Summer Greens): 4 closed sales in the last 12 months, $715,000 to $1,100,000

Rentals

Highland Woods permits leasing with a 30-day minimum, and seasonal rental demand is real, though the community is primarily owner-occupant and seasonal rather than an investor market. Current annual and seasonal rental rates vary widely by product type and season: annual leases start around $2,100 per month, off-season rates run roughly $1,600 to $5,500 per month, and in-season rates run roughly $4,900 to $9,500 per month (7 active MLS rental listings on the pull date; no MLS-recorded closed leases in the last 12 months). See the Renting and Investing section for the full leasing rules and amenity-transfer requirements.

What the numbers mean for you

A snapshot is only useful in context, and context is exactly what a community specialist provides. Whether the current numbers favor buyers or sellers, and by how much at each tier, changes through the season and by product type. McGreevy and Comisar read this market every day and can tell you precisely where your home sits in it, or where a home you want to buy is priced relative to recent comparable sales. For a current, tier-specific market read on Highland Woods, call Jesse at (239) 898-6072 or Marc at (239) 287-5873.

HOA, Governance and Fees at Highland Woods

Highland Woods uses a two-tier governance structure: a single master, member-owned club corporation over roughly 15 to 18 neighborhood sub-associations. The master club (Highland Woods Golf & Country Club, Inc.) is resident-governed by a nine-member Board of Trustees and self-managed on site, while each condominium neighborhood runs its own board and management company. Crucially, Highland Woods has no CDD, so buyers pay only their neighborhood dues plus the master club dues, with no district bond debt (sunbiz N95000000818; Lee County Tax Collector; hwgcc.com).

Understanding the governance stack is how you understand your fees, and Highland Woods' structure is clean and well documented.

Tier 1: the master, member-owned club

At the top is Highland Woods Golf & Country Club, Inc., a Florida not-for-profit corporation (sunbiz N95000000818, filed 02/20/1995) that owns and governs the community-wide amenities, the common grounds, the roads inside the gates, the gatehouse, and the mandatory bundled membership. It is run by a Board of Trustees and a General Manager and administered from the club's on-site Admin Office at 9100 Highland Woods Blvd (main line 239-495-9332). The club's governance is genuinely resident-controlled: every current officer and trustee on the most recent state filing lives inside the community, on streets like Summer Greens Drive, Clarkston Drive, and Highland Woods Boulevard (sunbiz N95000000818). The Board is structured so trustees represent the community's neighborhood associations, and the developer completed turnover to member control by 2002 (Amended and Restated Articles filed 07/08/2002). The same top-tier body functions as the "Master Association" that sets the resale capital contribution, collects the tenant transfer fee, and enforces community-wide rules on common grounds, parking, and signage (Rules and Regulations v1.10; 2026 Master Association Schedule of Fees, hwgcc.com).

Tier 2: the neighborhood sub-associations

Beneath the master club, each condominium and veranda neighborhood is its own Florida not-for-profit association with its own recorded declaration, bylaws, board, budget, reserves, and management company. The single-family Summer Greens homes and the attached Villas are platted-lot product governed at the master and neighborhood level rather than as separate condo regimes (Florida DBPR Condominium Registry; hwgcc.com Real Estate page). What this means in practice: an owner in a condo or veranda neighborhood pays two levels of dues, their own neighborhood association dues (set by that association's budget and collected by its manager) plus the community-wide master club dues. The neighborhood dues vary by association and are disclosed on each unit's estoppel; they are not published community-wide, so we obtain the exact figure for your specific building as part of any transaction.

No CDD: a genuine financial advantage

Highland Woods has no Community Development District, and this is provable from the tax bill rather than merely asserted. We read an actual 2025 Lee County Tax Collector bill for a Highland Woods parcel (STRAP 27-47-25-B1-0170L.0030) and confirmed the entire tax obligation is standard countywide and regional ad-valorem millage (2025 combined millage 12.7970), with no CDD line item and no non-ad-valorem CDD assessment (Lee County Tax Collector, parcel 27-47-25-B1-0170L.0030, 2025 bill; Lee County Property Appraiser, Folio 10439257). This is exactly what you would expect for a mid-1990s community whose infrastructure was financed by the developer and the club rather than through CDD bonds. Many newer Southwest Florida golf communities carry a CDD bond that adds a fixed annual assessment for decades; Highland Woods does not. The community's capital needs are instead met through the club's Replacement Reserve Fund and periodic dues adjustments, which is why the reserve line in the dues grew from $950 to $2,500 between 2025 and 2026 (2026 Master Association Schedule of Fees, hwgcc.com).

A note on condo structural laws

Florida's post-Surfside condominium laws (the mandatory Milestone Inspection under s. 553.899 and the Structural Integrity Reserve Study under s. 718.112) target buildings of three stories or more. The Highland Woods condominium product, the Verandas coach homes and the Terrace and Heathermoor garden condos, is low-rise, generally two stories, which materially limits the community's exposure to the large structural special assessments seen at three-story-plus coastal high-rises (Florida DBPR Condominium Registry building types; Rules and Regulations v1.10 describing two-story product; Florida SIRS/milestone statutes). Any specific building's reserve study is a member-restricted document obtained via estoppel, and we review it as part of a purchase.

The management companies

The community runs a mixed model: the master club is self-managed on site, and each neighborhood contracts its own property manager. Current assignments per the club's official roster include Alliant, Compass Rose, Resort Management, Tropical Isles, NextGen, and Gulf Breeze across the various condo and villa neighborhoods, with the Single Family homes self-managed under a resident president (hwgcc.com Real Estate page; 2026 Master Association Schedule of Fees). Assignments shift over time, so we confirm the current manager and dues for your specific neighborhood at transaction time.

The recorded documents

Highland Woods' governing documents are public record and, where retrievable, we cite them directly. The master governing instrument is the recorded Declaration of Covenants, Conditions and Restrictions (Lee County Official Records Book 2612, Pages 3397-3485, recorded 06/26/1995), and the community sits in Section 27, Township 47 South, Range 25 East, with the Phase Three plat recorded at Plat Book 59, Pages 95-101 (Lee County Clerk of Courts; Lee County Property Appraiser). The club's Articles of Incorporation and their amendments (2002 and 2013), the annual reports, and the current fee schedule are all public and linked in the Downloadable Documents section below. This documentary transparency is part of what makes Highland Woods straightforward to buy into: the governance, the fees, and the rules are all on the record.

For a full walk-through of the governance stack and exactly what your neighborhood's dues and the master club dues add up to, call Jesse at (239) 898-6072 or Marc at (239) 287-5873. McGreevy and Comisar are part of Domain Realty and handle the estoppel and disclosure process on every Highland Woods transaction.

What It Costs to Own in Highland Woods

Owning at Highland Woods means budgeting three ongoing layers plus one-time closing costs: the 2026 master club dues of $13,812.79 per year, your neighborhood association dues (which vary by neighborhood), and ordinary Lee County property taxes with no CDD assessment, plus a one-time buyer-paid capital contribution of $10,000 and an estoppel fee of $250 to $450 at closing. The exact total depends on your product type and neighborhood (Highland Woods 2026 Master Association Schedule of Fees; Lee County Tax Collector, hwgcc.com).

Southwest Florida golf-community carrying costs can be confusing because they stack several fees, and buyers deserve a plain, honest breakdown. Here is what it actually costs to own in Highland Woods, separating the recurring costs from the one-time costs, and flagging exactly which figures are fixed and known versus which vary by home.

The cost-of-ownership breakdown

Sources: Highland Woods 2026 Master Association Schedule of Fees (hwgcc.com); Lee County Tax Collector, parcel 27-47-25-B1-0170L.0030, 2025 bill; Lee County Property Appraiser, Folio 10439257. Live property-tax figures depend on the specific home's assessed value and homestead status.

Recurring versus one-time

Recurring (annual): the master club dues ($13,812.79 for 2026), your neighborhood association dues (varies), the $500 Food and Beverage minimum, and Lee County property taxes (varies by assessed value, with no CDD). Note that the master club dues and the F and B minimum are identical for every home in Highland Woods, from the smallest condo to the largest single-family home. What varies between owners is the neighborhood association dues and the property-tax bill, both of which scale with the home.

One-time (at purchase): the $10,000 resale capital contribution and the $250-to-$450 estoppel fee, both paid by the buyer at closing on separate checks to the club. These are not annual costs; they are your one-time entry into the equity membership.

The flat-membership effect on affordability

The single most important thing to understand about Highland Woods carrying costs is that the club-level cost is roughly the same whether you buy the entry condo or the premium home. Because every home pays the same master club dues, the same F and B minimum, and the same capital contribution, the golf-and-club portion of ownership does not scale up with the home price. That is what makes a Heathermoor condo one of the most cost-efficient ways in Bonita Springs to own a full, immediate, no-waitlist equity golf membership: you get the identical club, course, and amenities as a Summer Greens homeowner, at a fraction of the real estate price. It also means the true carrying-cost gap between the entry tier and the premium tier is narrower than the purchase-price gap suggests, because so much of the ongoing cost is the flat club membership.

The no-CDD savings

It is worth stating the CDD advantage in dollars-and-sense terms. In many newer Southwest Florida golf communities, a CDD bond assessment adds a fixed charge, often in the low-to-mid four figures annually, to every owner's tax bill for 20 to 30 years to repay infrastructure bonds. At Highland Woods, that line does not exist. Over a typical ownership period, the absence of a CDD assessment is a meaningful cumulative saving versus a comparable bonded community, and it is one of the honest financial advantages of buying into an established community like this one (Lee County Tax Collector, parcel 27-47-25-B1-0170L.0030).

Get an exact number for a specific home

Because the neighborhood dues and the property-tax figure vary by home, the only way to get a precise total cost of ownership for a specific Highland Woods property is to pull that unit's neighborhood association dues and its actual tax bill. That is exactly what McGreevy and Comisar do for every buyer, so you walk into a purchase knowing your real all-in monthly and annual cost, with no surprises at the estoppel. For a precise, home-specific cost-of-ownership analysis, call Jesse at (239) 898-6072 or Marc at (239) 287-5873. McGreevy and Comisar are part of Domain Realty, and we handle the fee verification on every Highland Woods transaction.

Location and Lifestyle in Highland Woods

Highland Woods sits on the east side of US-41 (Tamiami Trail South) at the West Terry Street corridor in Bonita Springs, one of the most convenient addresses in Southwest Florida. From the gate at 9100 Highland Woods Blvd, the nearest Publix is at the US-41 and Bonita Beach Road intersection, the Gulf beaches are a few miles west, Coconut Point is minutes north, and RSW airport is about 20 to 25 minutes away.

That location is the whole convenience thesis for Highland Woods. Bonita Beach Road runs straight west from the community to the Gulf, US-41 runs north to the mall and the airport and south to Naples, and everyday shopping sits essentially at the front gate. The club markets its setting as beautiful beaches, abundant shopping, popular restaurants, entertainment venues, and an international airport all within minutes, and the geography backs that up.

Drive times from Highland Woods

Distances and times below are approximate, measured from the Highland Woods entrance at 9100 Highland Woods Blvd, using typical driving routes. Actual times vary with traffic and the winter season. Your agent can run an exact door-to-door time for any specific listing.

Beaches and the Gulf

Bonita Beach Road runs west from near the community straight to the Gulf. Lee County's Bonita Beach Access points, including Access #10 at Little Hickory, offer nearby public sand, and the adjacent Barefoot Beach Preserve County Park is a roughly 342-acre barrier-island preserve on Little Hickory Island reached off Barefoot Beach Boulevard. For Highland Woods owners, a morning at the beach is a short drive rather than a day trip.

Shopping and dining

Coconut Point in Estero is a picturesque outdoor mall with more than 110 stores including Nordstrom Rack, Dillard's, Super Target, Apple, Barnes & Noble, and a PGA TOUR Superstore, on US-41 just south of Corkscrew Road at I-75 Exit 123, immediately north of Highland Woods. The Promenade at Bonita Bay is an upscale open-air center of boutiques, salons, and restaurants on US-41 in Bonita Springs. A few miles south, Mercato in North Naples pairs a Whole Foods Market with dining, a cinema, and nightlife at US-41 and Vanderbilt Beach Road. Downtown Bonita Springs along Old 41 adds a walkable historic district on the Imperial River with Riverside Park, a bandshell, artist cottages, outdoor concerts, and city festivals such as Celebrate Bonita, Star Spangled Bonita, and Taste of Bonita.

RSW airport

Southwest Florida International Airport (RSW) is the Lee County Port Authority airport, described by the City of Bonita Springs as just 20 minutes from Bonita Springs, with 20-plus airline partners and nonstop service across North America plus international service. That easy airport access is one of the practical reasons seasonal buyers and second-home owners are drawn to the Bonita Springs corridor, and Highland Woods sits squarely on it.

An honest word on walkability

Highland Woods is a car-dependent suburban golf community, and it is worth being straight about that. Inside the gates it is genuinely pleasant to walk or bike, with low-traffic boulevards, a 20 mph community speed limit, manicured grounds, and lake and fairway views, and residents can easily reach the clubhouse and pools on foot. Outside the gate, everyday errands require a car. US-41 is a busy multi-lane arterial, not a pleasant pedestrian route, and the beaches, malls, downtown, and airport all require driving. The honest framing is a walking-and-cart lifestyle inside the gate and a car lifestyle outside it, which is typical for golf communities in this part of Florida.

If you want the neighborhood-by-neighborhood picture inside the gate, dedicated sub-pages for St. Andrews Verandas, Terrace, Heathermoor, Highland Woods Villas, and the Summer Greens single-family homes are coming, with fee schedules, recent comps, and street-level detail, and will be linked here when live.

Schools for Highland Woods

Highland Woods is served by the School District of Lee County, and its zoned middle school sits essentially next door. Bonita Springs Middle Center for the Arts (grades 6-8) is on West Terry Street immediately adjacent to the community's US-41 entrance. The zoned high school is Bonita Springs High School (grades 9-12, opened 2019), and elementary students attend through Lee County's proximity and choice model, with two Bonita Springs elementaries in zone. Always verify your exact address on the district's official SchoolSite Locator.

Lee County does not use a simple one-address-to-one-school rule at every level. It uses a Residential and Choice Zone structure: the county is divided into large zones, each split into proximity sub-zones. Elementary families choose among the schools within their proximity zone, while middle and high assignments are more directly geographic. The 2026-2027 Plan for Student Enrollment was approved by the School Board on December 1, 2025. Because zones and choice options can change year to year, the correct step for a home purchase is to confirm the current-year assignment for the exact address on the Lee County SchoolSite Locator.

The zoned and proximity schools

Bonita Springs Middle Center for the Arts (grades 6-8). Located at 10141 West Terry Street, Bonita Springs, this is the Bonita Springs public middle school and sits on West Terry Street, immediately adjacent to the Highland Woods entrance, a genuine short-walk or short-drive convenience. It enrolls roughly 706 students at about a 17-to-1 student-teacher ratio. Confirm the current Florida Department of Education letter grade on the state report card for the most recent year.

Bonita Springs High School (grades 9-12). Located at 25592 Imperial Parkway, Bonita Springs, this is a newer South Lee County high school that opened for the 2019-2020 school year, built to relieve overcrowding at Estero High School and serve the growing Bonita Springs population. As a result, the Highland Woods area now feeds Bonita Springs High School rather than Estero High. Advanced Placement coursework is offered. The Florida Department of Education recorded a "B" grade for the school in its most recent released data.

Spring Creek Elementary (K-5) and Bonita Springs Elementary (PK-5). These are the two Bonita Springs public elementaries within the local proximity zone. Spring Creek Elementary is at 25571 Elementary Way, and Bonita Springs Elementary is at 10701 Dean Street SE. A Highland Woods family will typically have both available in zone and should confirm current options and any capacity or waitlist status on the SchoolSite Locator and with the district's Student Enrollment office.

District context

The School District of Lee County maintained an overall "B" district grade for 2024-2025 from the Florida Department of Education. In that grading cycle, 14 Lee County schools earned an A and 27 earned a B, no Lee County school received an F, and the district continued to rank ninth among Florida districts.

Private and charter options nearby

Families weighing alternatives to the zoned schools have several nearby choices to research directly for tuition, grade span, and availability. Bonita Springs Charter School is a Cognia-accredited, tuition-free public charter (application and lottery based) at 25380 Bernwood Drive, Bonita Springs. Grace Classical Academy is a private classical Christian K-8 school in Bonita Springs. 3 Oaks Academy is a private K-12 school in Estero with small ratios and learning-difference support. Royal Palm Academy is a Catholic private school in North Naples. Additional independent and faith-based schools operate across Estero, Bonita Springs, and North Naples.

Healthcare Near Highland Woods

Highland Woods has two 24/7 freestanding emergency rooms within a few miles, both on the US-41 corridor: the Lee Health Coconut Point Emergency Department in Estero to the north and the NCH Bonita Springs Freestanding Emergency Department on US-41 in Bonita Springs. Walk-in urgent care is available in Bonita Springs, and the nearest full inpatient hospitals are NCH North Naples to the south and Gulf Coast Medical Center in Fort Myers to the north.

For a community that skews toward seasonal residents, retirees, and second-home owners, proximity to good emergency and everyday care is a real quality-of-life factor, and Highland Woods is well positioned on it.

Emergency rooms

Lee Health Coconut Point Emergency Department, 23450 Via Coconut Point, Estero, is a full-service, freestanding 24/7 emergency department on the Lee Health Coconut Point campus, east of US-41 near Coconut Road just north of Highland Woods. The campus also houses outpatient services, imaging, and lab.

NCH Bonita Springs Freestanding Emergency Department, 24040 South Tamiami Trail (US-41), Bonita Springs, is a 24/7 freestanding emergency department operated by the NCH Healthcare System, on US-41 in Bonita Springs a short drive from the community.

Urgent care and walk-in

Lee Health Convenient Care in Bonita Springs offers walk-in urgent care for minor emergencies and illnesses seven days a week, associated with the Bonita Community Health Center on Health Center Boulevard, a campus tied to both Lee Health and NCH.

Full-service hospitals

The nearest full inpatient acute-care hospitals are the NCH North Naples Hospital Campus at 11190 Healthpark Blvd, Naples, roughly 9 to 12 miles south, and Gulf Coast Medical Center (Lee Health) at 13681 Doctors Way, Fort Myers, roughly 15 miles north. Both operate 24/7 emergency departments in addition to full inpatient services.

Everyday needs

Grocery and pharmacy are close. Publix at The Center of Bonita Springs, at the US-41 and Bonita Beach Road intersection, includes a Publix Pharmacy and sits essentially at the community's front door. Publix at Grande Oak Shoppes in Estero is a short drive north. National-chain pharmacies operate along US-41 and Bonita Beach Road. In short, the daily-needs infrastructure around Highland Woods, from groceries to emergency care, is dense and close, which is a meaningful part of the community's appeal.

Hurricane, Flood Zones and Insurance in Highland Woods

Flood risk in Highland Woods is mixed and address-specific. The entrance and the southern and central residential areas are in FEMA Zone X (minimal-risk), where flood insurance is not federally required, while the northern and northeastern interior near the natural drainage corridor and community lakes is in Zone AE (Special Flood Hazard Area, base flood elevation 9 feet), where flood insurance is required on a mortgage. Verify any specific parcel on the FEMA Flood Map Service Center or Lee County flood maps.

This is one of the most important and most misunderstood topics for buyers, so it is worth walking through carefully and honestly. Highland Woods sits inland off US-41, roughly 4 to 5 miles from the Gulf, which materially shapes its storm profile, but "inland" does not mean "no flood zone," and the answer genuinely changes from one part of the community to another.

The flood-zone picture: Zone X versus Zone AE

Because Highland Woods spans a large footprint, a single flood zone does not describe the whole community. Point-by-point queries of the Lee County Property Appraiser's official flood-zone layer, which reflects the effective FEMA Flood Insurance Rate Map, return the following pattern:

What this means in plain terms:

• Zone X is not a Special Flood Hazard Area. Federally regulated lenders do not require flood insurance for a Zone X home. The "shaded X" designation here is the 0.2% annual chance (500-year) band, lower risk than the 1% (100-year) Special Flood Hazard Area, and still not a mandatory-purchase zone. Even so, flood insurance in Zone X is inexpensive (a low-risk NFIP policy can run a few hundred dollars a year) and is smart in coastal Southwest Florida, since a standard homeowners policy never covers flood.
• Zone AE is a Special Flood Hazard Area (the 1% annual chance, 100-year floodplain). A federally backed mortgage on an AE-zone home will require flood insurance, and the base flood elevation here is 9 feet. The AE floodway on the northeast edge is the most development-restricted band. These AE areas track a natural drainage corridor and the community's lakes.

The practical takeaway is simple: in Highland Woods the flood-zone answer is address-specific. Many of the southern and central homes are Zone X with no federal flood-insurance mandate, while some homes closer to the interior drainage corridor and lakes are Zone AE with a mandate. A flood-zone determination, and an Elevation Certificate for AE homes, should be pulled for every specific listing, and your agent can do that before you write an offer.

The 2022 FEMA remap

New Lee County Flood Insurance Rate Maps became effective November 17, 2022 (a process that had been in preliminary and appeal status since 2019, separate from Hurricane Ian). Highland Woods was significantly enough affected that the City of Bonita Springs ran a documented series of community-specific outreach meetings for Highland Woods residents and its Board of Association Presidents through 2022 and 2023, covering the new maps, Letter of Map Change options, and flood-insurance requirements. If you own or are buying here, this is a live, well-documented local topic, and it is another reason to confirm the current zone for the exact parcel.

The flood-insurance discount: CRS Class 5

Here is a genuine financial advantage. For 17 years Lee County has held a FEMA Community Rating System rating of Class 5, which gives policyholders a 25% discount on National Flood Insurance Program premiums. In 2024, FEMA reviewed the rating and there was a real scare that it could be lost, but after corrective action the City of Bonita Springs and Lee County were notified on November 21, 2024 that they would maintain the Class 5 rating and the 25% discount. (Neighboring Fort Myers Beach was placed on probation and lost its discount, but that does not apply to Highland Woods, which is in the City of Bonita Springs.) That 25% discount is a real, ongoing reduction on flood premiums for every Highland Woods policyholder, in both X and AE zones.

Wind zone and building code: 160 mph, but not the HVHZ

The Bonita Springs area carries a 160 mph design wind speed and is part of Florida's Wind-Borne Debris Region, meaning new construction and replacement windows and doors must be protected against windborne debris with impact-rated products or code-approved shutters. It is important to be accurate here: Highland Woods is not in the High Velocity Hurricane Zone (HVHZ). The HVHZ, with its stricter 170 to 180-plus mph design speeds and Miami-Dade product-approval requirements, applies only to Miami-Dade and Broward counties. Buyers sometimes conflate the two. The accurate statement is Wind-Borne Debris Region, not HVHZ. Homes built or updated to the current Florida Building Code, with impact windows or shutters, meet code and can earn insurance wind-mitigation credits.

How Highland Woods actually fared in recent storms

This is where the inland position matters, and it should be stated without minimizing that these storms were historic disasters for coastal Lee County.

Hurricane Ian (September 2022). Ian made landfall near Cayo Costa as a near-Category-5 storm. The catastrophic 10 to 15 foot storm surge hit the immediate coast (Fort Myers Beach, Estero Island, Bonita Beach). Per the National Hurricane Center's official report, farther south in Bonita and North Naples the most severe impacts were contained to the immediate coastline, while inland high-water marks ranged from 5 to 7 feet above ground. Highland Woods, inland and east of US-41 and mostly in Zone X, was outside the worst of that surge. The citywide headline figure of 12-plus feet of surge is the coastal maximum at the beaches, not the inland experience at Highland Woods, and should not be applied to the community.

Hurricane Milton (October 2024). Milton made landfall near Siesta Key as a Category 3. In Bonita Springs, its flood damage concentrated in four areas west of Old 41 near the Imperial River (Hickory Island, Spring Creek, Imperial Shores, and the corridor from West Terry Street to Pennsylvania Avenue). Highland Woods, east of US-41, was not in the identified primary Milton damage corridor.

The honest caveat on evacuation. Lee County still maps Highland Woods in worst-case Evacuation Zone A (the first zone ordered to evacuate) and Storm Surge Zone 1. That is a maximum-of-maximums planning scenario, not a forecast of what any given storm will do, and in Ian the actual inland high-water marks in the Bonita area were far below the coastal surge. Both things are true and both belong on the table: Highland Woods is in a first-to-evacuate zone, so residents should plan to leave when ordered, and its inland position kept it out of the catastrophic surge in the recent major storms. Confirm the current evacuation-zone designation for any address on the official Lee County Know Your Zone lookup.

Note on the golf course and clubhouse in Ian

No primary source publishes a specific Hurricane Ian damage report for Highland Woods' course or clubhouse, so the page will not assert one. The club's own roughly $8.3 million "Project '22" renovation of the pool, pickleball, tennis, cafe, and golf shop is referenced by the club as complete. Buyers who want storm-history detail on a specific building should ask the relevant association during due diligence.

Condo and coach-home insurance mechanics

Because many Highland Woods residences are condominiums, verandas, and coach homes, master-policy mechanics matter to a large share of buyers. In these associations, the association's master policy insures the building structure and common elements, and the unit owner buys an HO-6 policy for the interior, contents, liability, and loss assessment. A few points to know:

• Florida requires a loss-assessment minimum. Florida Statute 627.714 requires a condo unit-owner residential policy to include at least $2,000 in loss-assessment coverage, which pays the owner's share of a special assessment (for example, to cover a master-policy deductible after a storm).
• The $2,000 minimum is usually not enough in coastal Florida. Master-policy hurricane deductibles are often percentage-based and can be large, so a unit owner's share of an assessment can far exceed $2,000. The common guidance is to carry substantially higher loss-assessment limits and to check whether the coverage applies toward the master-policy hurricane deductible.
• Ask for the structural reserve study. Florida's post-Surfside law (SB 4-D) requires Structural Integrity Reserve Studies and milestone inspections for condo buildings of three-plus stories, which has driven up assessments and reserves statewide. Buyers of Highland Woods condos should request each association's reserve study, reserve schedule, and any milestone-inspection status, and factor in potential special assessments.

This page keeps the condo-insurance discussion educational and does not state any Highland Woods association's specific master-policy terms, deductibles, or assessment history, because those are obtained during due diligence. Get each association's declaration, master-policy declarations page, reserve study, and recent assessment history before closing.

The insurance market is stabilizing

Florida property insurance got very expensive and hard to place in 2022 and 2023, but the market has meaningfully recovered in 2025 and 2026. State regulators approved more than 10 new property and casualty insurers to enter Florida after the 2022-2023 reforms, the average homeowners rate-change request fell to near flat (well under 1%), and Citizens, the state insurer of last resort, has shrunk below 1 million policies for the first time in over two years as private carriers assume policies. A Zone X home in Highland Woods with documented wind mitigation is a relatively favorable risk to insure in today's market.

Bottom line for buyers. Highland Woods sits inland off US-41, most of it in minimal-risk Zone X where flood insurance is not federally required, with a 25% CRS flood-insurance discount for every policyholder, a Wind-Borne Debris Region (not HVHZ) building standard, and a storm history that kept it out of the catastrophic surge in Ian and Milton. The real caveats are honest ones: some interior homes are in Zone AE with a flood-insurance requirement, the whole community is mapped in first-to-evacuate Zone A as a worst-case scenario, and condo buyers should study each association's reserves and assessment history. Verify the specifics for any exact address, and your agent will help you do it.

What's Coming Near Highland Woods

Near Highland Woods, the civic pipeline is broadly supportive of property values: walkability and drainage upgrades on the community's own West Terry Street corner, a major FDOT rebuild of the US-41 and Bonita Beach Road intersection to the south, a revitalizing Old 41 downtown, and large new retail and dining nodes a short drive away. The main caveat is construction-season disruption and general corridor traffic as Bonita Springs grows. Every item below is dated and status-flagged.

Knowing what is planned, approved, and under construction around a community is part of buying smart, so here is the honest read on the projects that shape Highland Woods.

At the community's own corner

West Terry Street sidewalk and drainage improvements (underway). West Terry Street is the cross street at Highland Woods' US-41 entrance, so this is the most locally relevant project. The City of Bonita Springs is adding a new sidewalk on the south side of West Terry from US-41 to Old 41 Road, plus a closed drainage system with curb and gutter, complementing a 12-foot shared-use path already completed in 2022 on the north side. A public meeting was held November 14, 2024, and the project is underway. This is a direct walkability and stormwater upgrade on the community's corner, a positive.

Roads

US-41 at Bonita Beach Road intersection reconstruction (approved, in design). This is the single most impactful road item, about 1.5 miles south of Highland Woods at the busiest intersection nearby. FDOT granted Location and Design Concept Acceptance on July 25, 2025 for a partial Displaced Left Turn design that lets left turns run at the same time as through traffic, plus a new northeast-quadrant connector road to Arroyal Road and a 12-foot shared-use path. It now proceeds to design. The value read is mixed: long-term congestion relief and walkability at a key gateway, but future construction disruption on the main route residents use to reach Coconut Point, Naples, and the beaches.

Old 41 four-lane widening (study, preferred alternative). FDOT's PD&E study to widen Old US-41 up to four lanes, roughly 1 to 2 miles west of Highland Woods, presented its preferred alternative at a public hearing on November 20, 2025, with the comment period closing December 1, 2025. Old 41 is the spine of the revitalizing downtown Bonita dining and entertainment district, so more capacity and multimodal features support that district, with construction as the trade-off. Value read: mixed to positive.

Downtown and retail

Old 41 downtown redevelopment (ongoing). A roughly one-mile stretch of Old 41 in downtown Bonita Springs, about 1 to 2 miles west of Highland Woods, is seeing a wave of new restaurants, bars, riverfront gathering spaces, and mixed-use redevelopment. A revitalized, walkable downtown a short drive away is a lifestyle amenity that supports area home values. Value read: positive.

The Center of Bonita Springs (established, reinvested). At US-41 and Bonita Beach Road, roughly 1.5 miles south, the area's busiest intersection anchors the nearest everyday-shopping node to Highland Woods, with a Publix and a large-format Rural King. It is owned by a national open-air retail REIT, which means ongoing reinvestment. Value read: positive.

Midtown at Bonita (under construction). A 68-acre mixed-use district on Bonita Beach Road east of I-75, roughly 3 to 4 miles east, broke ground on its retail component in November 2025. Plans call for about 400 luxury apartments, roughly 200,000 square feet of retail and office, and a 165-room boutique hotel, with signed tenants including T.J. Maxx, Ulta Beauty, Chipotle, Panera Bread, and Club Pilates, and first shops targeted for 2026. It is oriented to the east-of-I-75 node rather than the immediate US-41 doorstep, but it is a strong new retail, dining, and hotel amenity for the wider city that Highland Woods buyers reach with a short drive. Value read: positive for Bonita Springs overall.

Revana Lakes (approved). A 299-home, 100,000-square-foot mixed-use community on Bonita Beach Road east of I-75, roughly 3 to 4 miles east, was approved by Bonita Springs City Council on January 22, 2026 after a multi-year process, still subject to state review. It adds housing supply and some commercial to the corridor, though its removal of a Density Reduction and Groundwater Resource designation was locally controversial and it adds long-run east-side traffic. Not adjacent to Highland Woods; a corridor-perception item. Value read: mixed.

Stormwater, trails, and utilities

East Terry Street stormwater and multi-use pathway (contract awarded). The City awarded a roughly $17.8 million construction contract on April 1, 2026 for stormwater management, a 10-foot multi-use pathway, and water and wastewater improvements along East Terry Street. It is on the east and downtown side rather than at Highland Woods' immediate corner, but it adds flood resilience and walkability to the corridor. Value read: positive.

Bonita rail-to-trail (bond referendum pending August 18, 2026). The City placed a bond referendum on the August 18, 2026 primary ballot to fund land acquisition (a roughly $28.6 million city share) to convert an inactive rail corridor into a multi-use recreational trail, with 5.8 miles within Bonita Springs. If approved, a regional greenway would be a citywide lifestyle amenity. The outcome depends on the vote. Value read: potential plus.

Bonita Springs Utilities (established). Water and sewer in this area are served by Bonita Springs Utilities, a member-owned nonprofit cooperative named a 2025 Utility of the Future Today. It has run septic-to-central-sewer conversion programs for decades, and its ongoing modernization protects local waterways and supports property values. Highland Woods, as an established platted golf community off US-41, sits within BSU's service footprint.

The net read

The civic pipeline near Highland Woods is dominated by infrastructure upgrades (walkability and drainage), an improving downtown, and major new retail and amenity nodes, all broadly supportive of values. The main caveats are construction-season disruption and general corridor traffic as Bonita Springs continues to grow. No identified project specifically threatens Highland Woods.

The City of Bonita Springs incorporated in 1999 and operates under a mayor-council government, with Mayor Mike Gibson and six district council members. Council meets on the first and third Wednesdays of the month, and residents can look up their council district on the City's website.

Renting and Investing in Highland Woods

Highland Woods allows leasing with a 30-day minimum lease term, and an owner's club membership can transfer to a tenant through a documented Transfer of Membership process with fees and General Manager approval. The Rules and Regulations cap transfers at a maximum of 12 per year, and neighborhood association documents may impose longer minimums. Highland Woods is primarily an owner-occupant and seasonal community rather than a high-turnover rental market.

If you are weighing Highland Woods as an investment or a seasonal rental, here is how the leasing rules actually work.

The leasing rules

• 30-day minimum. The minimum rental period is 30 consecutive days. Highland Woods does not permit short-term or nightly vacation rentals, and individual neighborhood documents may require a longer minimum than 30 days.
• Membership transfers to the tenant. When owners are not in residence, they may temporarily transfer their amenity-use rights to a tenant through the Master Association's Transfer of Membership process. An executed transfer application must be submitted in advance, a transfer fee (tiered by length of stay and payable to the Master Association) must be paid, and the General Manager must approve. During a transfer, the owner's own privileges, including all golf play, are rescinded for that period.
• Maximum 12 transfers per year. Owners may transfer privileges a maximum of 12 times per year, and separate approval may be required from the relevant neighborhood management company.
• Transfer fee amounts are member-and-office only. The tiered dollar amounts of the owner-to-tenant Transfer of Membership Fee are not published publicly. Do not rely on a number you see quoted elsewhere; contact the club or your agent for the current schedule.

The investor read

Highland Woods works well for a seasonal owner who wants to lease during part of the year and use the home the rest of the time, and it is genuinely attractive for a snowbird or second-home buyer. It is less suited to a pure high-frequency short-term rental strategy, both because of the 30-day floor and because this is fundamentally a member-owned, owner-occupant golf community with a strong seasonal culture. The bundled equity membership adds a real amenity draw for a quality long-term or seasonal tenant, but the annual club dues and the one-time capital contribution the buyer pays at closing are carrying costs an investor has to underwrite. For a realistic rental-rate range and a return analysis on a specific unit, ask us to run the current rental comps.

For live rental numbers, 7 rentals are listed on the MLS today and asking rates run about $2,100 per month annual, $1,600 to $5,500 per month off-season, and $4,900 to $9,500 per month in season can be pulled at any time.

Thinking of Selling Your Highland Woods Home? List With the #1 Team in Southwest Florida Since 2012

If you're searching for the best Highland Woods listing agent, or thinking, "I need to sell my house in Highland Woods and get top dollar," McGreevy and Comisar is the team to call. We are the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse and Marc. Selling a bundled-golf home takes an agent who knows exactly how this market works. Sellers here hire us because the credentials are current and local: Top 1% Real Estate Agents Nationally Since 2008, and the #1 Team in Southwest Florida since 2012.

Selling in Highland Woods is not like selling a standard home. A buyer here is also buying into a member-owned equity club with a full golf membership, an annual due structure, and a one-time capital contribution at closing, and the right listing agent knows how to present all of that as value rather than let it become a hurdle. That is precisely the kind of nuance we handle every day.

Our credentials as your listing team

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 20 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and Team have sold over 2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

Our recent Highland Woods track record

When you list with us, you get a team with a proven, current record right here in the community:

• 36 homes sold in the last 12 months
• $17.4 million in dollar volume
• 88 days average time to contract
• 94.0 percent average sale-to-list ratio
• Highest-priced sold: $1,100,000
• Fastest sale: same-day contract days

Marketing that gets Highland Woods homes sold for more

The reason our sellers net more is the marketing. Every listing we take is presented like the premium Southwest Florida property it is:

• Cinematic listing video and aerial drone footage that show off the golf-course, lake, and fairway views Highland Woods buyers are looking for, plus the resort-style clubhouse and amenity lifestyle.
• Professional architectural photography that makes verandas, coach homes, villas, and single-family homes look their absolute best in the first three seconds a buyer sees them online.
• A qualified-buyer database built over more than a decade in this market, so your home is put in front of real, ready buyers, including the seasonal and second-home buyers who gravitate to bundled-golf communities, from day one.
• Full digital, social, and search exposure engineered so your listing reaches buyers wherever they are searching, backed by a team that lives and breathes Southwest Florida golf communities.
• Expert pricing and negotiation grounded in live Highland Woods comps and a clear-eyed read of what buyers will actually pay, so you list at the right number and defend it at the closing table.

Ready to find out what your Highland Woods home is worth?

Get a free, no-obligation home valuation at https://mcgreevyandcomisar.com/home-valuation, or call Jesse McGreevy directly at (239) 898-6072. We will give you a real number based on current Highland Woods sales, a clear marketing plan, and an honest conversation about timing. When you are ready to sell your Highland Woods home for the most the market will pay, list with the #1 team in Southwest Florida since 2012.

• Jesse McGreevy: (239) 898-6072, [email protected]
• Marc Comisar: (239) 287-5873
• Office: 24031 S. Tamiami Trail, Suite 101, Bonita Springs, FL 34135

Why McGreevy and Comisar

McGreevy and Comisar is the best real estate team for Highland Woods, whether you are buying or selling. We are the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse McGreevy and Marc Comisar. That track record, paired with deep knowledge of Bonita Springs bundled-golf communities like Highland Woods, is why buyers and sellers trust us with their most important transactions.

Real estate in a member-owned equity golf community rewards expertise. The dues structure, the capital contribution, the membership transfer at closing, the flood-zone nuances, the neighborhood association differences: these are exactly the details that separate a smooth, well-priced transaction from a stressful one, and they are exactly what our team handles every day across Southwest Florida.

Honors and recognition

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 20 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and Team have sold over 2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

Part of Domain Realty

McGreevy and Comisar are part of Domain Realty. Learn more about our full brokerage at DomainRealtyGroup.com.

Contact us

• Jesse McGreevy: (239) 898-6072, [email protected]
• Marc Comisar: (239) 287-5873
• Office: 24031 S. Tamiami Trail, Suite 101, Bonita Springs, FL 34135
• Brokerage: Domain Realty, DomainRealtyGroup.com

Whether you want a free valuation of your Highland Woods home, a private showing of a listing, or an honest conversation about whether a bundled-golf community is right for you, call Jesse at (239) 898-6072 or Marc at (239) 287-5873. We would be glad to help.

Frequently Asked Questions: Buying in Highland Woods

Buying in Highland Woods means buying a home plus a full equity golf membership in a member-owned bundled-golf community of about 799 residences in Bonita Springs, with no separate membership tiers, no golf waitlist, and no CDD. Below are detailed answers to the questions buyers ask most, grouped by topic, from golf and dues to flood zones, schools, and the buying process itself.

Golf and membership

Is golf membership required to buy in Highland Woods?

Yes, and that is the entire point of a bundled-golf community. Every one of the roughly 799 homes in Highland Woods carries a full Owner Equity Member golf membership, and it conveys automatically with the home. You do not choose whether to join, and you cannot buy a home here without the membership. This is why buyers get immediate golf access, and it is the defining feature of the community.

Is Highland Woods a bundled golf community?

Yes. Highland Woods is a true bundled-golf, member-owned equity club. The cost of the golf membership is bundled into ownership rather than sold separately, so every homeowner is automatically a full golf member. This is different from optional-membership communities, where golf is an add-on some residents buy and others skip.

Do you automatically become a golf member when you buy a home in Highland Woods?

Yes. The moment you own a home in Highland Woods, you are an Owner Equity Member with full golf privileges. There is no separate application to join the golf club and no initiation fee to become a member. Membership activates once the warranty deed and the closing fees reach the club's administration office, typically within a day or two.

What type of golf membership comes with a Highland Woods home, golf or social?

Golf. Highland Woods has one membership type, a full Owner Equity Member golf membership, not separate golf and social tiers. Every home carries the same full-golf membership, so you are not choosing between a golf level and a lower social level as you would at some clubs. Everyone has the same access.

Is there a difference between a golf membership and a social membership at Highland Woods?

No, because there is only one membership. Some clubs sell a cheaper social membership that excludes golf, but Highland Woods does not. There is a single Owner Equity Member category that includes full golf, so the golf-versus-social distinction simply does not apply here. This keeps the community's membership base equal and capped at the home count.

How many golf memberships are there at Highland Woods?

Membership is capped at the community's size, roughly 799, because each home carries exactly one membership and no memberships are sold to non-residents. That cap is a real benefit: the course is used only by members and their guests, which helps keep tee-time availability reasonable and protects the value of the membership every homeowner holds.

Who designed the Highland Woods golf course?

The Highland Woods golf course was designed by Gordon Lewis and built in 1995. Lewis is a well-known Southwest Florida golf architect, and the course was built using xeric principles to preserve the natural terrain, set among the natural preserves and waterways of Bonita Springs. It is one of the reasons the community has a mature, established feel rather than a brand-new look.

How many holes is the Highland Woods golf course, and what is the par and yardage?

Highland Woods is an 18-hole, par-72 championship course. It plays roughly 6,799 yards from the tips per the current scorecard, with multiple tee sets so players of different abilities can enjoy it. It was designed by Gordon Lewis and built in 1995, and it has been reinvested in significantly since, including regrassing and greens work.

Is the Highland Woods golf course private or public, and can non-residents play?

It is private. The Highland Woods course is for members and their accompanied, registered guests, not the general public. Non-residents cannot simply book a public tee time. Guests may play when accompanied by a member and registered with the golf shop in advance, and they pay posted guest fees. This member-and-guest-only access is part of what makes the bundled membership valuable.

Is there a golf waitlist at Highland Woods, or do you get immediate golf access?

There is no waitlist. Because every home comes with a full golf membership, you have immediate golf access the moment you close. This is a genuine advantage over communities where you buy the home first and then wait, sometimes for years, for a golf membership to become available. In Highland Woods, closing day and golf day are effectively the same.

Is golf unlimited at Highland Woods, and are there cart fees?

Golf play is included with your Owner Equity Membership rather than charged per round, and members enjoy the course throughout the season. Cart and certain incidental fees can apply and are set by the club, and private personally owned golf carts are not permitted on the property. For the current cart-fee and play details, ask your agent or the club's golf shop, since specifics are set by the Board and can change.

What practice facilities and renovations does the Highland Woods golf course have?

Highland Woods has practice facilities including a driving range, plus an on-course turn window (the Cabana) for a bite between nines. The course and club have seen major reinvestment, including roughly $6.5 million in 2016 (with regrassing and greens work) and a roughly $8.3 million "Project '22" that upgraded the pool, pickleball, tennis, cafe, and golf shop. That ongoing reinvestment is a sign of a healthy, well-run club.

Fees, dues, and the bundled-golf concept

What is a bundled golf community, and how does it work at Highland Woods?

A bundled-golf community is one where golf membership is included with home ownership rather than purchased separately. At Highland Woods, every home carries a full Owner Equity Member golf membership automatically, so the annual club dues appear on every owner's budget and everyone has full golf access. You cannot own here without the membership, and you never wait for or bid on one.

What is the difference between bundled golf and equity golf?

Highland Woods is both. Bundled means the golf membership is tied to the home and conveys with it. Equity means the members collectively own the club rather than a private developer or investor owning it. So in Highland Woods, buyers get a membership bundled with the home in a club the members themselves own, which aligns the community's interests with keeping the club and course in top condition.

Is there an initiation fee at Highland Woods?

No traditional initiation fee to join the golf club, because membership conveys with the home. What a buyer does pay at closing is a one-time Resale Capital Contribution to the club, set at $10,000 for 2026 (up from $6,500 in 2025). That is different from a country-club initiation fee: it is a capital contribution paid at purchase, and it funds the club's capital needs.

How much are the annual dues at Highland Woods?

The annual club dues are $13,812.79 for 2026, up from $10,815.36 in 2025. These are the master club dues, set annually by the Board, and they cover the golf, clubhouse, amenities, reserves, and bundled cable and internet. This is the master-club figure only; a buyer also pays their specific neighborhood or condo association dues on top of it.

Is there a food and beverage minimum at Highland Woods?

Yes. Highland Woods has a $500 annual food and beverage minimum, meaning you are expected to spend at least that much per year in the club's dining venues (the Grille Room, the Dining Room, and the poolside Woods Cafe). For most active members this is easy to meet, and it is a common and modest requirement for a club of this type.

Why does Highland Woods have both a master club due and a neighborhood fee?

Because it has a two-tier structure. The master club and association covers the golf course, clubhouse, main amenities, and shared common areas for the whole community, funded by the annual master dues. Below that, each neighborhood (the condo, veranda, terrace, villa, and single-family associations) has its own association covering that neighborhood's buildings, grounds, insurance, and reserves, funded by neighborhood dues. So you pay both, and the neighborhood amount varies by where you buy.

What is the resale capital contribution, estoppel fee, and transfer fee at Highland Woods?

The buyer pays a one-time Resale Capital Contribution of $10,000 at closing for 2026. There is also an estoppel fee of roughly $250 to $450 (with possible add-on charges to update or expedite). An owner-to-tenant Transfer of Membership Fee exists for leasing situations, but its dollar tiers are member-and-office only and are not published, so confirm the current schedule with the club or your agent rather than relying on a quoted number.

Are there special assessments at Highland Woods, and what do the dues cover?

The master dues cover golf, the clubhouse and dining, the amenities, reserves, a preserve-maintenance fund, and bundled cable and internet. Like any club, Highland Woods can levy special assessments for major capital projects, and condo buyers in particular should review each association's reserve study and recent assessment history during due diligence. For the current status on any specific building, ask your agent to obtain the association documents before you write an offer.

Do the HOA fees at Highland Woods vary by neighborhood or home type?

Yes. The master club dues are the same for every home, but the neighborhood or condo association dues differ by which association you buy into, since a condo building, a coach-home veranda, an attached villa, and a self-managed single-family home each have different maintenance, insurance, and reserve needs. Your agent can pull the exact current association dues for any specific listing.

Is there a CDD at Highland Woods?

No. Highland Woods has no Community Development District. This is proven from the Lee County tax bill, which shows no CDD line and no non-ad-valorem CDD assessment. That means no CDD bond and no annual CDD assessment on top of your taxes and dues, a genuine cost advantage over many newer golf communities that carry CDD debt for decades.

Homes, inventory, and the buying process

How many homes are in Highland Woods, and what types are there?

Highland Woods has roughly 799 residences spanning single-family homes plus attached and condominium product. The named groups include the St. Andrews Verandas (coach-home condos, the largest group), the Terrace condos, Heathermoor (entry-tier condos), the Highland Woods Villas (attached villas), and the self-managed single-family homes in the Summer Greens area. So a buyer can choose from an entry condo up to a premium single-family home, all sharing the same bundled membership.

What is the difference between a veranda and a coach home at Highland Woods?

In Highland Woods, the St. Andrews Verandas are the coach-home-style condominiums, typically stacked two-story buildings where each unit has its own entry and often a one-car garage, many with lake, fountain, or fairway views. The terms veranda and coach home are used for this attached-condo product. Villas, by contrast, are attached single-story homes, and Summer Greens offers detached single-family homes. Your agent can walk you through which product fits your needs.

When were the homes in Highland Woods built, and is it built out?

Highland Woods was master-planned and platted in the mid-1990s, with the golf course built in 1995 and home construction running roughly 1996 to 2000. The community is built out, so there is no new construction from a developer; inventory is resale. That established, mature character, with grown landscaping and a settled club, is part of the appeal for many buyers.

Do Highland Woods homes have golf course views, lake views, and garages?

Many do. The community was designed among lakes, fountains, and fairways, and a large share of homes overlook water or the golf course, which is a frequent selling point in listings here. Garage availability depends on the product type, with many coach homes offering a garage and single-family homes and villas typically including one. For the specific view and garage on any listing, ask your agent.

How much do homes cost in Highland Woods, and what is the price range?

Highland Woods spans a wide range, from entry-tier condos (Heathermoor resale has historically started around the high-$100Ks to low-$200Ks) up to premium single-family homes reaching roughly $800K or more. Prices move with the market, so for the current, accurate range and the median, ask us for a live pull. The last 12 months of closings ran from $198,000 to $1,100,000 and a $415,000 median reflect today's numbers.

What is the buying process for a bundled-golf home in Highland Woods?

It looks like a normal Florida home purchase with a few community-specific steps. You tour and select a home, write an offer, and go under contract. During due diligence, your agent obtains the association documents, the master and neighborhood budgets and reserves, and a flood-zone determination for the exact parcel. At closing, you pay the one-time capital contribution and the estoppel fee, and your Owner Equity Membership activates within a day or two of the deed and fees reaching the club office. We guide sellers and buyers through every one of these steps.

What should I know before buying in Highland Woods?

Know that you are buying a home plus a full equity golf membership, so budget for the annual club dues (currently $13,812.79), your neighborhood association dues, the $500 food-and-beverage minimum, and the one-time $10,000 capital contribution at closing. Know that there is no CDD, no golf waitlist, and no membership tiers. And know that flood zone, pet rules, and reserves are address- and building-specific, so verify them for the exact home. Working with an agent who knows the community, like our team, makes all of it straightforward.

Lifestyle, amenities, and community rules

What amenities does Highland Woods have?

Highland Woods offers an 18-hole Gordon Lewis golf course, an updated clubhouse with multiple dining venues, seven heated pools including a resort-style zero-entry main pool with a Jacuzzi and poolside cafe, six pickleball courts, four lighted tennis courts, a three-court bocce complex, and a 24-hour two-level fitness center. There is a manned gatehouse, a 20 mph community speed limit, and a state-protected gopher tortoise preserve on the property. It is a full country-club amenity set for a mid-sized community.

Does Highland Woods have pickleball, tennis, and bocce?

Yes to all three. Highland Woods has six dedicated pickleball courts (with open play, a ball machine, loaner paddles, and ambassadors for newcomers), lighted tennis courts, and a bocce complex with seasonal leagues for men, women, and couples. Racquet sports are a big part of the social calendar here. Note that the club's own materials have shown slightly different tennis and bocce court counts over time as it renovated, so confirm the current configuration with the club.

How many pools does Highland Woods have, and is there a fitness center?

Highland Woods has seven heated community pools. The main clubhouse pool is a resort-style, zero-entry pool with a Jacuzzi and the poolside Woods Cafe, and six additional pools are spread through the condominium and veranda neighborhoods, including one covered pool. The fitness center is a two-level facility built in 2016 and open 24 hours, with an equipment room, a mirrored group-exercise studio, a certified trainer, and classes. Water aerobics runs six days a week.

What dining options does Highland Woods have, and was the clubhouse renovated?

Highland Woods has three dining venues: the casual Grille Room overlooking the 18th green, a formal Dining Room for events and dinner nights, and the poolside Woods Cafe. Yes, the clubhouse was renovated, most recently through the roughly $8.3 million "Project '22," which added the resort-style pool, the Woods Cafe, and upgraded pickleball, tennis, and the golf shop, following an earlier roughly $6.5 million renovation in 2016.

Does Highland Woods have an active social calendar, and what is it like to live there?

Yes, very active, especially in season (October through April). The calendar includes bocce, tennis, and pickleball leagues and socials, Tuesday game nights, Sunday breakfast buffets, and marquee parties (Welcome Back, New Year's Eve, Valentine's Day, End of Season, St. Patrick's Day). The club describes itself as warm and welcoming, with members from all over the country, and an active-yet-relaxed lifestyle. Summers are quieter, with reduced club hours, which tells you it is a genuine seasonal community.

Is Highland Woods a 55-plus or age-restricted community?

No. Highland Woods is an all-ages community, not a 55-plus or age-restricted one. Children are allowed to live here. In practice the community skews toward seasonal residents, retirees, and second-home owners because of its golf-club character, but there is no age restriction, and families are welcome.

Is Highland Woods gated and safe?

Yes, Highland Woods is a private, gated community with a manned gatehouse that controls entry, a dedicated gatekeeper line, and a 20 mph community speed limit. Visitors are routed to the visitors gate, and guests using amenities must be registered. The manned gate and controlled access are part of the community's appeal and its everyday sense of security.

What is the pet policy at Highland Woods?

Pets are part of community life but are restricted in amenity areas: animals are not allowed in the pool areas or on the golf course. The specific number, size, and breed limits are set by each neighborhood association's condo or HOA documents, not the master rules, so your exact pet allowance depends on which building or neighborhood you buy in. Confirm the pet rules for the specific association at contract, and your agent will pull them for you.

Location, schools, and flood

Where is Highland Woods located, and what county and city is it in?

Highland Woods Golf & Country Club is at 9100 Highland Woods Blvd, Bonita Springs, in Lee County, Florida, ZIP 34135. Its main entrance is on the east side of US-41 (Tamiami Trail South) at the West Terry Street corridor, just north of West Terry Street. It is in the City of Bonita Springs, east of US-41 and west of I-75, which puts it minutes from shopping, beaches, and the airport.

How far is Highland Woods from the beach, Coconut Point, and RSW airport?

The Gulf beaches (Bonita Beach, Barefoot Beach) are roughly 4 to 6 miles west, about a 10 to 15 minute drive. Coconut Point outdoor mall in Estero is roughly 3 to 4 miles north, about 8 to 10 minutes. RSW airport is roughly 19 to 21 miles, about 20 to 30 minutes. The nearest Publix, at US-41 and Bonita Beach Road, is essentially at the front gate. It is a very convenient location.

What schools serve Highland Woods?

Highland Woods is in the School District of Lee County. The zoned middle school, Bonita Springs Middle Center for the Arts (grades 6-8), sits immediately adjacent on West Terry Street. The zoned high school is Bonita Springs High School (grades 9-12, opened 2019). Elementary uses Lee County's proximity-and-choice model, with Spring Creek Elementary and Bonita Springs Elementary in zone. Always confirm the exact address on the district's official SchoolSite Locator, since zones can change.

Is Highland Woods in a flood zone, and do you need flood insurance?

It depends on the exact home. Most of Highland Woods (the entrance and southern and central areas) is in FEMA Zone X, where flood insurance is not federally required, though a low-cost policy is still smart. Some interior homes near the drainage corridor and lakes on the north and northeast are in Zone AE, where flood insurance is required with a mortgage. Verify the specific parcel on the FEMA Flood Map Service Center, and note that the whole area benefits from a 25% CRS flood-insurance discount.

Did Highland Woods flood during recent hurricanes?

Highland Woods sits inland off US-41, roughly 4 to 5 miles from the Gulf, and it was outside the catastrophic coastal storm surge in Hurricane Ian (2022), where the 10 to 15 foot surge hit the immediate coast and inland Bonita high-water marks ran 5 to 7 feet. In Hurricane Milton (2024), Bonita's flood damage concentrated west of Old 41 near the Imperial River, not at Highland Woods. The community is still mapped in worst-case Evacuation Zone A, so residents plan to leave when ordered, but its inland position kept it out of the worst recent surge.

Are Highland Woods homes required to have hurricane shutters?

The Bonita Springs area is a Wind-Borne Debris Region with a 160 mph design wind speed, so new construction and replacement windows and doors must be protected with impact-rated products or code-approved shutters. It is not the stricter High Velocity Hurricane Zone, which applies only to Miami-Dade and Broward. Homes with impact windows or shutters meet code and can earn insurance wind-mitigation credits, which is worth confirming on any specific home.

Comparisons and neighborhoods

How does Highland Woods compare to other Bonita Springs golf communities, and is it a good value?

Highland Woods is frequently cited as a strong-value bundled-golf option in Bonita Springs, with an established Gordon Lewis course, a fully renovated amenity package, an equity membership every owner shares, and, importantly, no CDD. The combination of immediate golf with no waitlist, a member-owned club, and no CDD debt is a genuine value story. We can give you a candid, side-by-side read of Highland Woods versus other area communities based on current dues, prices, and what you want out of the lifestyle. We keep those comparisons factual and tailored to you.

What are the neighborhoods in Highland Woods?

Highland Woods is organized into named associations: the St. Andrews Verandas (coach-home condos, the largest group, roughly 350 units), the Terrace condos, Heathermoor (entry-tier condos), the Highland Woods Villas (attached villas), and the self-managed single-family homes in the Summer Greens area. Each has its own association and management company. Dedicated sub-pages for each neighborhood, with fee schedules, recent comps, and street-level detail, are coming and will be linked here when live.

Who manages the HOA at Highland Woods, and how do I contact the club?

Highland Woods has a master board and general manager over the club, plus separate management companies for each neighborhood association (including firms handling the various Verandas, Terrace, Heathermoor, and Villas buildings, and a self-managed single-family group). The club's administrative office and general manager can be reached at the main club number, and the official site is hwgcc.com. For which management company handles a specific building and how to obtain documents or an estoppel, your agent can point you to the right contact.

Still have questions about buying in Highland Woods?

Call Jesse McGreevy at (239) 898-6072 or Marc Comisar at (239) 287-5873, or email [email protected]. As the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold, McGreevy and Comisar can answer any Highland Woods question and show you the homes that fit. Our office is at 24031 S. Tamiami Trail, Suite 101, Bonita Springs, FL 34135.

Frequently Asked Questions: Selling in Highland Woods (Seller Edition)

Selling in Highland Woods means marketing a home plus a full equity golf membership, which is a real advantage when handled by the right listing agent. Below are the questions sellers ask most, from what your home is worth and how fast homes sell, to the membership transfer at closing, the fees you pay, and why McGreevy and Comisar, the #1 team in Southwest Florida since 2012, is the team to list with. As Top 1% Real Estate Agents Nationally Since 2008 and a top-reviewed Highland Woods team, we answer these questions for owners every week.

Home values and the market

What is my Highland Woods home worth?

Your Highland Woods home's value depends on its neighborhood (condo, veranda, villa, or single-family), its size, its view (golf, lake, or fountain views command a premium), its condition and updates, and current market conditions. The most accurate answer comes from live comparable sales in the community. Get a free, no-obligation valuation at https://mcgreevyandcomisar.com/home-valuation or call Jesse at (239) 898-6072, and we will give you a real number, not a computer estimate. The community's 36 closed sales of the last 12 months, from $198,000 condos to $1,100,000 single-family homes, anchor the analysis.

What is my Highland Woods condo worth?

Condo values in Highland Woods vary by building group. Heathermoor is the entry tier, the Terrace and St. Andrews Verandas coach homes sit above that, and view and floor level matter a great deal. Because association dues and reserves differ by building, a buyer weighs those too. We price your condo against the most recent sales in your specific association, not the community average, which is how you get an accurate number. Call us for a current condo valuation.

What have homes sold for in Highland Woods, and what is the median sale price?

Sold prices in Highland Woods span from entry condos to premium single-family homes, and the median moves with the market, so live numbers matter. For the current figures, ask us for a fresh pull. 36 sold last year at $17.4 million in volume, with a median of $415,000 and recent sold prices ranging from $198,000 to $1,100,000.

Are home values in Highland Woods going up or down?

Highland Woods values track the broader Bonita Springs and Southwest Florida golf-community market, and the direction shifts with season, inventory, and interest rates. Rather than guess, we will show you the actual trend in the community's recent sales and months of supply. The last 12 months' 36 closed sales at a $415,000 median and $302 average per square foot and 2.7 months of supply tell the real story, and we will interpret them honestly for your specific home and neighborhood.

Do Highland Woods homes hold their value, and is it a good investment?

Highland Woods has durable value drivers: an established Gordon Lewis course, a member-owned equity club, a fully renovated amenity package, no CDD debt, and a convenient US-41 location minutes from beaches and the airport. Bundled-golf communities with no waitlist and no CDD tend to hold appeal for the steady stream of seasonal and second-home buyers in this market. As with any home, value depends on price, condition, and timing, and we will give you a clear-eyed read for your situation.

How fast do homes sell in Highland Woods, and what is the average days on market?

Days on market in Highland Woods varies with price point, season, and how well a home is prepared and priced. Recent snapshots have shown days on market running roughly in the 80-to-115-day range, but that changes, so use a live number. Recent sales averaged 88 days on market and 88 reflect current conditions. Homes that are professionally marketed and correctly priced consistently sell faster, which is exactly what our team delivers.

How many homes are currently for sale in Highland Woods, and what is the months of supply?

Active inventory and months of supply move constantly, so these should always be pulled live. 8 homes are currently for sale, representing 2.7 months of supply months of supply. We monitor this in real time, because whether it is a seller's or a more balanced market directly affects your pricing strategy and how we position your home. Ask us for today's numbers.

Selling process, fees, and the membership transfer

Who is the best realtor or listing agent to sell a home in Highland Woods?

McGreevy and Comisar is the best team to sell your Highland Woods home. We are the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse and Marc. We know how to market a bundled-golf home so buyers see the membership as value, and our premium marketing (cinematic video, drone, professional photography, and a deep qualified-buyer database) nets sellers more. Call Jesse at (239) 898-6072.

How do I sell my home in Highland Woods?

Start with an accurate valuation and a marketing plan. We tour your home, price it against live Highland Woods comps, and prepare it to show at its best. We produce professional photography, cinematic video, and drone footage, then launch it across digital, social, and search, and into our qualified-buyer database. We manage showings, negotiate offers, coordinate the estoppel and membership transfer, and guide you to the closing table. The first step is a free valuation: call Jesse at (239) 898-6072 or visit https://mcgreevyandcomisar.com/home-valuation.

What do I need to do to sell a bundled-golf condo in Highland Woods?

Selling a bundled-golf condo has a few community-specific steps beyond a standard sale. Your listing must present the golf membership as the value it is, and the buyer will review your association's budget, reserves, and any assessments, so having those documents ready helps. The membership conveys to the buyer, the buyer pays the one-time capital contribution at closing, and an estoppel is ordered from the club and the association. We handle all of it, and we know exactly how to market the coach-home and condo product here.

Does the golf membership transfer when I sell my Highland Woods home?

Yes. The Owner Equity Member golf membership is tied to the home and conveys to the buyer at closing. You are not selling the membership separately, and the buyer does not join a waitlist; they become a full golf member as soon as the sale closes and the club activates the new owner. This automatic transfer is a major selling point, and we make sure buyers understand the value they are getting.

What fees does a seller pay at closing in Highland Woods?

A seller pays the standard Florida closing costs (such as the brokerage commission, documentary stamp taxes on the deed, title-related costs per your contract, and prorated dues and taxes). Note that the one-time Resale Capital Contribution ($10,000 for 2026) is paid by the buyer, not the seller. There is also an estoppel fee (roughly $250 to $450) to produce the club and association estoppel. We will give you a clear net-proceeds estimate up front so there are no surprises.

What is the estoppel process when selling in Highland Woods?

When your home goes under contract, an estoppel is ordered from the club (and from your neighborhood association) that states the current dues, any amounts owed, and the fees due at closing. The estoppel fee runs roughly $250 to $450, with possible add-ons to update or expedite. Once the buyer's warranty deed and closing fees reach the club's administration office, the new owner's membership activates, typically within a day or two. We coordinate the estoppel so it does not delay your closing.

How much is the resale capital contribution the buyer pays, and does it affect my sale?

The buyer pays a one-time Resale Capital Contribution of $10,000 for 2026 (up from $6,500 in 2025). It does not come out of your proceeds, but it is part of the buyer's total cost of entry, so a skilled listing agent frames it correctly as the price of stepping into a member-owned equity club with immediate golf. We know how to present the full ownership picture so it strengthens your sale rather than becoming an objection.

How do buyers view the annual dues when I sell, and how do you handle that?

Informed buyers who seek out a bundled-golf community expect annual club dues, and they weigh them against the value of immediate, waitlist-free golf in a member-owned club with a renovated amenity set and no CDD. Our job as your listing agent is to make sure buyers see that value clearly, with the right comparisons and marketing, so the dues read as what they buy rather than just a cost. That framing is a big part of why our listings sell.

Timing, preparation, and marketing

When is the best time to sell a home in Highland Woods?

Highland Woods is a seasonal community, and buyer activity is typically strongest in the winter season (roughly October through April), when seasonal residents and second-home buyers are in town. That said, the right price and marketing sell homes year-round, and listing in a lower-inventory window can work in your favor. We will look at current inventory, recent sales, and your personal timeline and recommend the smartest listing window for your specific home.

What should I do to prepare my Highland Woods home to sell?

Focus on first impressions and the details buyers here care about: clean and declutter, address any deferred maintenance, and make sure the view (golf, lake, or fountain) is showcased. We advise on cost-effective updates and staging that pay off, then bring in professional photography, cinematic video, and drone footage so your home looks its best in the first three seconds online. A pre-listing walkthrough with our team will give you a specific, prioritized plan.

How will you market my Highland Woods home?

Every listing we take gets premium marketing: professional architectural photography, cinematic listing video, aerial drone footage of the home and the community's golf and lake setting, full digital, social, and search exposure, and placement in our qualified-buyer database built over more than a decade in this market. We market to the seasonal and second-home buyers who gravitate to bundled-golf communities, and we back it with expert pricing and negotiation. This is how our sellers consistently net more.

Why should I list with McGreevy and Comisar instead of another agent?

Because results and expertise. McGreevy and Comisar is the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and a 5 Star Award for Customer Satisfaction for 20 straight years (only 5 out of 21k-plus licensees, per Gulfshore Life Magazine). We know Highland Woods and Bonita Springs bundled-golf communities intimately, we market at a premium level, and we negotiate hard for your bottom line. Call Jesse at (239) 898-6072.

Do you handle both the club estoppel and the neighborhood association paperwork?

Yes. Selling in Highland Woods involves both the master club and your specific neighborhood association, and we coordinate the estoppels and document requests for both so nothing falls through the cracks or delays closing. We know which management company handles each building group and how to obtain the documents buyers will request. Managing these moving parts smoothly is part of the full-service listing experience we provide.

Can you sell my Highland Woods home if I live out of state or out of the country?

Absolutely. Many Highland Woods owners are seasonal or second-home owners who are not in Florida year-round, and we regularly list and sell homes for out-of-area owners. We handle the preparation, marketing, showings, negotiation, and closing coordination, and we keep you fully informed remotely. Distance is not an obstacle; call Jesse at (239) 898-6072 or email [email protected] and we will make it seamless.

How do I get started selling my Highland Woods home?

The first step is a free, no-obligation home valuation. Visit https://mcgreevyandcomisar.com/home-valuation or call Jesse McGreevy directly at (239) 898-6072. We will give you an accurate value based on current Highland Woods sales, a clear marketing plan, and an honest conversation about timing and net proceeds. When you are ready to sell for the most the market will pay, list with the #1 team in Southwest Florida since 2012.

More seller questions

Does having no CDD help me when I sell my Highland Woods home?

Yes, it is a real selling point. Highland Woods has no Community Development District, so there is no CDD bond and no annual CDD assessment layered onto a buyer's cost, which many competing golf communities do carry. A savvy buyer notices the difference in total cost of ownership. We make sure your listing highlights the no-CDD advantage, because it is a genuine reason a buyer may choose Highland Woods over a comparable community with CDD debt.

Should I update my Highland Woods home before selling, or sell as-is?

It depends on your home, your timeline, and the return on each improvement. Some updates (fresh paint, flooring, kitchen and bath refreshes, and anything that showcases the view) reliably pay back at sale, while others do not. We give you an honest, prioritized recommendation on what is worth doing and what is not, so you do not overspend. In some cases, selling as-is at the right price to the right buyer is the smarter move, and we will tell you straight.

How do golf-course, lake, and fountain views affect my sale price?

Significantly. In Highland Woods, homes overlooking the golf course, a lake, or a fountain typically command a premium over interior-facing units, and the quality of the view is one of the first things buyers weigh. When we price and market your home, we account for your specific view and make sure our photography and video capture it, because in a community built around water and fairways, the view is a major part of what a buyer is paying for.

Do I need to disclose the flood zone when I sell my Highland Woods home?

Florida sellers must disclose known material facts, and flood history and flood-zone status are increasingly important to buyers. Since the flood zone in Highland Woods is address-specific (Zone X for much of the community, Zone AE for some interior homes near the drainage corridor and lakes), we help you obtain the accurate determination for your exact parcel so it is presented correctly. Being upfront and accurate about flood zone and any storm history protects your sale and your closing.

How does the seasonal market affect how long my home takes to sell?

Highland Woods is a seasonal community, so buyer traffic is typically heaviest in winter (October through April) when seasonal residents and second-home shoppers are in town, and lighter in summer when club hours scale back. That rhythm can affect days on market. We factor the season into your pricing and launch strategy, and even in the quieter months, correct pricing and premium marketing keep well-presented homes moving. We will advise on the best window for your goals.

What happens to my club membership and dues when the sale closes?

Your Owner Equity Member golf membership conveys to the buyer at closing rather than being cashed out to you, since it is tied to the home. Your dues are prorated to the closing date as part of the settlement, and the buyer takes over from there and pays the one-time capital contribution to the club. We coordinate the proration and the club's activation of the new owner so the handoff is clean, and we explain exactly how it works before you list.

How do I price my Highland Woods home correctly in a changing market?

Correct pricing starts with the most recent comparable sales in your specific neighborhood and product type, adjusted for your home's view, condition, and updates, then read against current inventory and buyer demand. Overpricing in a seasonal market can leave a home sitting; underpricing leaves money on the table. We build your price from live Highland Woods data, not a formula, and we revisit it as the market moves. Get started with a free valuation: call Jesse at (239) 898-6072.

Still have questions about selling in Highland Woods?

Call Jesse McGreevy at (239) 898-6072 or Marc Comisar at (239) 287-5873, or email [email protected]. McGreevy and Comisar, part of Domain Realty, is the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse and Marc. Our office is at 24031 S. Tamiami Trail, Suite 101, Bonita Springs, FL 34135. Learn more about our brokerage at DomainRealtyGroup.com.

Downloadable Documents and Public Records

The public records below govern and describe Highland Woods, from the recorded plats and master Declaration to the club's own fee schedules and rules, plus the government flood, road, and school documents relevant to the community. Each is a real, official document. For now, each is cited on its authoritative source URL (government, official club, county, state, or federal). At our WordPress migration, these will be self-hosted here for easy download.

Recorded instruments and corporate records (Lee County Clerk and sunbiz)

Official club documents (hwgcc.com)

Tax, flood, and hazard records (county, FEMA, and city)

Road, civic, and school records (FDOT, city, and state)

Note: some Highland Woods materials, including per-neighborhood recorded condominium declarations, current association budgets and reserves, structural reserve studies, the owner-to-tenant transfer-fee dollar tiers, and all member-login club content, are member-restricted or obtained only through estoppel and due diligence. Those are not published here. Your agent can obtain the applicable documents for a specific home during the transaction.

Sources

Every fact on this page traces to a primary source: government agencies, the official club (hwgcc.com), the Florida Division of Corporations (sunbiz), Lee County, FEMA, FDOT, the National Hurricane Center, universities and school authorities, official venue sites, and reputable news media. No competitor real estate or aggregator sites were used.

Official club (Highland Woods Golf & Country Club)

1. Highland Woods Golf & Country Club, official site: https://www.hwgcc.com/
2. Highland Woods, Contact / Directions: https://www.hwgcc.com/contact-us
3. Highland Woods, Real Estate (management companies, transfer of membership, documents): https://www.hwgcc.com/real-estate
4. Highland Woods, Hours of Operation: https://www.hwgcc.com/hours-of-operation
5. Highland Woods, Racquet Sports (tennis and pickleball): https://www.hwgcc.com/racquetsports
6. Highland Woods, Fitness: https://www.hwgcc.com/fitness
7. Highland Woods, Bocce: https://www.hwgcc.com/bocce
8. Highland Woods, Pools: https://www.hwgcc.com/pools
9. Highland Woods, Grille Room: https://www.hwgcc.com/grille-room
10. Highland Woods, Woods Pool Cafe: https://www.hwgcc.com/the-woods-pool-cafe
11. Highland Woods, Dining Room: https://www.hwgcc.com/dining-room
12. Highland Woods, Around the Club: https://www.hwgcc.com/around-the-club
13. Highland Woods, Rules & Regulations v1.10 (12/18/2023): https://www.hwgcc.com/documents/20124/0/Rules%20%26%20%20Regs%20version%201.10%20%20%20%2012.18.2023%282%29.pdf/273cfb35-8330-3af9-19bd-3e8e6866e502
14. Highland Woods, 2026 Master Association Schedule of Fees: https://www.hwgcc.com/documents/20124/291310/Estoppel+Info+2026.pdf/600cd9a6-2d92-aa80-152c-7dc907705c49
15. Highland Woods, 2025 Master Association Schedule of Fees: https://www.hwgcc.com/documents/20124/0/Estoppel%20Info%202025%283%29.pdf/593b2404-ef0f-d7a3-ca45-e806e1972fab
16. Highland Woods, 2025 Golf Scorecard: https://www.hwgcc.com/documents/20124/221608/2025+Scorecard+Final+PDF.pdf
17. Highland Woods, Community Map: https://www.hwgcc.com/documents/20124/0/Community%20Map-2%281%29.pdf/5ddb5913-ee90-b801-b1d3-a5d2f6da8f45

Recorded instruments and corporate records (Lee County Clerk, sunbiz) 18. Master Declaration of CC&Rs, OR Book 2612, Pages 3397-3485 (Lee County Clerk Official Records): https://or.leeclerk.org/LandMarkWeb/Document/GetDocumentByBookPage/?booktype=OR&booknumber=2612&pagenumber=3397 19. Recorded Plat, Highland Woods Phase One, Plat Book 57, Pages 1-9: https://or.leeclerk.org/LandMarkWeb/Document/GetDocumentByBookPage/?booktype=P&booknumber=57&pagenumber=1 20. Recorded Plat, Highland Woods Phase Three, Plat Book 59, Pages 95-101: https://or.leeclerk.org/LandMarkWeb/Document/GetDocumentByBookPage/?booktype=P&booknumber=59&pagenumber=95 21. sunbiz, Highland Woods Golf & Country Club, Inc. entity detail (N95000000818): https://search.sunbiz.org/Inquiry/CorporationSearch/SearchResultDetail?inquirytype=EntityName&directionType=Initial&searchNameOrder=HIGHLANDWOODSGOLFCOUNTRYCLUB%20N950000008180&aggregateId=domnp-n95000000818-984d7e18-f125-41e5-a3c9-cde1869d83aa&searchTerm=Highland%20Woods 22. sunbiz, Bonita Bay Properties, Inc. (developer general partner): https://search.sunbiz.org/Inquiry/CorporationSearch/SearchResultDetail?inquirytype=EntityName&directionType=Initial&searchNameOrder=BONITABAYPROPERTIES%20M092341&aggregateId=domp-m09234-0f83fb07-45ed-4d6b-8376-7d7622d2739e&searchTerm=Bonita%20Bay%20Properties 23. sunbiz, U.S. Home Corporation (production homebuilder, later Lennar): https://search.sunbiz.org/Inquiry/CorporationSearch/SearchResultDetail?inquirytype=EntityName&directionType=Initial&searchNameOrder=USHOME%20F000000020861&aggregateId=forp-f00000002086-96960554-2ff9-4acd-acf0-ba08f46dbc65&searchTerm=US%20Home%20Corp 24. Lee County Clerk of Courts, Official Records search portal: https://www.leeclerk.org/departments/official-records-services/search-official-records

Lee County property, tax, and hazard data 25. Lee County Tax Collector, 2025 tax bill parcel 27-47-25-B1-0170L.0030 (no-CDD proof): https://lee.county-taxes.com/public/real_estate/parcels/27-47-25-B1-0170L.0030 26. Lee County Property Appraiser, tax estimator (Folio 10439257; Highland Woods Ph III legal): https://www.leepa.org/taxestimator/default.aspx?FolioId=10439257 27. Lee County Property Appraiser, HazardsFloodZones MapServer, Flood Zones layer: https://gissvr.leepa.org/gissvr/rest/services/HazardsFloodZones/MapServer/3 28. Lee County Property Appraiser, HazardsFloodZones MapServer, Wind Speed layer: https://gissvr.leepa.org/gissvr/rest/services/HazardsFloodZones/MapServer/5 29. Lee County Property Appraiser, HazardsFloodZones MapServer, Evacuation / Storm Surge layer: https://gissvr.leepa.org/gissvr/rest/services/HazardsFloodZones/MapServer/7 30. Lee County, Know Your Evacuation Zone: https://www.leegov.com/publicsafety/emergencymanagement/knowyourzone 31. Lee County Flood Insurance Study 12071CV001D: https://www.leegov.com/dcd/Documents/Flood/FIS/12071CV001D.pdf 32. Lee County FIRM panel 12071C0676F: https://gisftpdata.leegov.com/PDFs/AGOL/FIRM/12071C0676F.pdf 33. Lee County FIRM panel 12071C0657F: https://gisftpdata.leegov.com/PDFs/AGOL/FIRM/12071C0657F.pdf

FEMA, National Hurricane Center, and flood insurance 34. FEMA Flood Map Service Center (by-address search): https://msc.fema.gov/portal/search 35. FEMA Bulletin W-24005, Notice of Potential NFIP Probation in Lee County: https://agents.floodsmart.gov/sites/default/files/bulletins/W-24005/w-24005.pdf 36. National Hurricane Center, Hurricane Ian Tropical Cyclone Report (AL092022): https://www.nhc.noaa.gov/data/tcr/AL092022_Ian.pdf 37. Florida Statute 627.714 (condo unit-owner loss-assessment minimum): https://www.leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0600-0699/0627/Sections/0627.714.html 38. Florida Office of Insurance Regulation, market release (01/27/2025): https://floir.gov/home/2025/01/27/commissioner-mike-yaworsky-approves-over-10-property---casualty-insurers-to-enter-the-market-following-historic-reforms 39. Citizens Property Insurance, Discounts (wind mitigation, FBC compliance): https://www.citizensfla.com/discounts 40. Citizens Property Insurance, Wind Mitigation Inspections: https://www.citizensfla.com/wind-mitigation-inspections

City of Bonita Springs (government) 41. City of Bonita Springs, FEMA Community Rating System page (CRS Class 5 / 25% discount): https://www.cityofbonitasprings.org/FEMACRS 42. City of Bonita Springs, Flood Protection Information (11/17/2022 FIRMs): https://www.cityofbonitasprings.org/services___departments/communications_department/emergency_resources/flood_protection_information 43. City of Bonita Springs, Communications & Community Outreach report (Highland Woods outreach log): https://cdnsm5-hosted.civiclive.com/UserFiles/Servers/Server_11726458/File/Communications%20and%20Community%20Outreach_Rev4.pdf 44. City of Bonita Springs, Flood Hazard Reduction Ordinance 22-05: https://cdnsm5-hosted.civiclive.com/UserFiles/Servers/Server_11726458/File/Ordinance%20No.%2022-05%20Flood%20Hazard%20Reduction.pdf 45. City of Bonita Springs, About / History (incorporated 1999): https://www.cityofbonitasprings.org/about_us/history 46. City of Bonita Springs, Mayor & Council: https://www.cityofbonitasprings.org/government/mayor___council 47. City of Bonita Springs, Airports (RSW): https://www.cityofbonitasprings.org/discover_bonita_springs/about_bonita_springs/airports 48. City of Bonita Springs, Things to Do: https://www.cityofbonitasprings.org/discover_bonita_springs/things_to_do 49. City of Bonita Springs, Council advances rail-to-trail funding to vote: https://www.cityofbonitasprings.org/news/what_s_new/city_council_advances_rail-to-_trail_funding_to_vo 50. City of Bonita Springs, West Terry Street public meeting notice: https://www.cityofbonitasprings.org/news/what_s_new/the_city_of_bonita_springs_will_host_a_public_meet 51. City of Bonita Springs, East Terry Street improvements: https://www.cityofbonitasprings.org/services___departments/public_works/east_terry_street_improvements

FDOT and roads 52. FDOT SWFL Roads, US 41 at Bonita Beach Road project (444321-1): https://www.swflroads.com/project/444321-1 53. FDOT, US 41 at Bonita Beach Road, Approved Type 2 Categorical Exclusion Determination Report: https://www.swflroads.com/project-files/126/444321%20US%2041%20at%20Bonita%20Beach%20Road%20Approved%20Type%202%20CE%20Determination%20Report.pdf 54. FDOT SWFL Roads, Old 41 (CR 887) four-lane widening PD&E (435110-1): https://www.swflroads.com/project/435110-1

Schools (district, state, federal) 55. Lee County Schools, School Zones page: https://www.leeschools.net/student_enrollment/school_zones 56. Lee County SchoolSite Locator (address lookup): https://www.schoolsitelocator.com/apps/leecounty/ 57. Lee County Schools, 2026-2027 Student Enrollment Plan: https://www.leeschools.net/common/pages/GetFile.ashx?key=c5aKDQZk 58. Bonita Springs Middle Center for the Arts: https://bnm.leeschools.net/ 59. Bonita Springs High School: https://bnh.leeschools.net/ 60. Spring Creek Elementary School: https://spc.leeschools.net/ 61. Bonita Springs Elementary School: https://bne.leeschools.net/ 62. Florida Department of Education, School Grades 2024 data (XLSX): https://www.fldoe.org/file/18534/SchoolGrades24.xlsx 63. Florida Department of Education, 2024-25 School Grades Results Packet: https://www.fldoe.org/file/18534/SchoolGradesResultsPacket25.pdf 64. Florida DOE, Know Your Schools report-card portal: https://edudata.fldoe.org/ReportCards/Schools.html 65. National Center for Education Statistics, school detail records: https://nces.ed.gov/ccd/schoolsearch/

Healthcare 66. Lee Health, Coconut Point Emergency Department: https://www.leehealth.org/locations/find-a-location/coconut-point-emergency-room 67. Lee Health, Convenient Care Bonita (urgent care): https://www.leehealth.org/locations/find-a-location/convenient-care-bonita 68. Lee Health, Gulf Coast Medical Center: https://www.leehealth.org/locations/find-a-location/gulf-coast-medical-center 69. NCH, Bonita Freestanding Emergency Department: https://locations.nchmd.org/fl/bonita-springs/nch-emergency-department-bonita-freestanding 70. NCH North Naples Hospital Campus (Florida Health Finder profile): https://quality.healthfinder.fl.gov/Facility-Provider/Profile/?LID=10147

Everyday needs, venues, and utilities 71. Publix, The Center of Bonita Springs (grocery + pharmacy): https://www.publix.com/locations/1449-the-center-of-bonita-springs 72. Publix, Grande Oak Shoppes (Estero): https://www.publix.com/locations 73. Simon, Coconut Point mall: https://www.simon.com/mall/coconut-point 74. Promenade at Bonita Bay: https://promenadeshops.com/ 75. Experience Mercato (North Naples): https://experiencemercato.com/ 76. Lee County, Bonita Beach Access #10 (Little Hickory): https://www.leegov.com/parks/beaches/littlehickory 77. Friends of Barefoot Beach, The Preserve: https://friendsofbarefootbeach.org/the-preserve/ 78. Bonita Springs Utilities, Inc. (BSU): https://bsu.us/

News media and directory corroboration 79. WGCU, unincorporated Lee County keeps flood discount (11/21/2024): https://www.wgcu.org/government-politics/2024-11-21/unincorporated-lee-county-keeps-flood-program-discount-fort-myers-beach-does-not 80. Naples Daily News, Hurricane Milton in Bonita Springs (damage areas, Imperial River): https://www.naplesnews.com/story/news/local/2024/10/25/hurricane-milton-left-its-mark-on-bonita-springs-damaging-homes-beaches/75824736007/ 81. WGCU, Lee County maintains B school rating (July 2025): https://www.wgcu.org/education/2025-07-09/school-grades-issued-lee-county-maintains-b-rating-mostly-as-bs-for-others-in-southwest-florida 82. Gulfshore Business, Midtown rises as Bonita Springs growth shifts east: https://www.gulfshorebusiness.com/development/midtown-rises-as-bonita-springs-growth-shifts-east/article_51d53e99-0b38-460a-8192-e028db89bd81.html 83. News-Press, Revana Lakes approved by City Council (01/23/2026): https://www.news-press.com/story/marketplace/real-estate/bonita-springs/2026/01/23/revana-lakes-gets-green-light-from-city-council-in-bonita-springs/88301215007/ 84. GolfPass, Highland Woods course listing (built 1995, Gordon Lewis): https://www.golfpass.com/travel-advisor/courses/1903-highland-woods-golf-country-club

Key Takeaways

Highland Woods is an established, member-owned bundled-golf community of about 799 homes in Bonita Springs, where every home carries a full equity golf membership with no tiers and no waitlist, there is no CDD, and the location off US-41 puts beaches, shopping, top schools, and RSW airport minutes away. Here is the community at a glance.

• True bundled equity golf. Every one of the roughly 799 homes in Highland Woods carries a full Owner Equity Member golf membership. There is one membership type (no separate golf-versus-social tiers), no initiation fee to join, and no golf waitlist, so buyers have immediate golf access at closing.
• A Gordon Lewis course and a renovated club. The 18-hole, par-72 course was designed by Gordon Lewis and built in 1995, set among preserves and waterways. The club has reinvested heavily, including roughly $6.5 million in 2016 and roughly $8.3 million in "Project '22," which upgraded the resort-style pool, cafe, pickleball, tennis, and golf shop.
• A full amenity set. Highland Woods offers seven heated pools, six pickleball courts, lighted tennis, a bocce complex, a 24-hour fitness center, three dining venues, a manned gate, and an active seasonal social calendar (October through April).
• The real cost of ownership. Buyers budget the 2026 annual club dues of $13,812.79, their neighborhood or condo association dues, a $500 food-and-beverage minimum, and a one-time $10,000 Resale Capital Contribution paid at closing. Dues are reset annually by the Board.
• No CDD. Highland Woods has no Community Development District, proven by the Lee County tax bill, so there is no CDD bond and no annual CDD assessment, a genuine cost advantage over many newer golf communities.
• A range of homes. Product spans entry-tier Heathermoor condos, Terrace condos, the St. Andrews Verandas coach homes, Highland Woods Villas, and Summer Greens single-family homes, built roughly 1996 to 2000, now a built-out resale community. Dedicated neighborhood sub-pages are coming.
• Address-specific flood risk. Most of Highland Woods is FEMA Zone X (flood insurance not federally required); some interior homes near the drainage corridor and lakes are Zone AE (required with a mortgage). The area holds a 25% CRS flood-insurance discount, uses a 160 mph wind standard (not the HVHZ), and its inland position kept it out of the catastrophic surge in Ian and Milton. Verify the exact parcel.
• Great location and schools. Off US-41 at West Terry Street, the community is minutes from the nearest Publix, the Gulf beaches, Coconut Point, and RSW airport, with the zoned Bonita Springs Middle Center for the Arts next door and Bonita Springs High School (opened 2019) nearby.
• Leasing is allowed, with rules. A 30-day minimum lease, membership transfer to tenants (maximum 12 per year), and transfer fees make Highland Woods suited to seasonal and long-term rentals rather than short-term vacation rentals.
• List with the best. McGreevy and Comisar is the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 Billion in real estate sold and $900 million in personal sales between Jesse and Marc. Whether you are buying or selling in Highland Woods, call Jesse at (239) 898-6072 or Marc at (239) 287-5873, email [email protected], or get a free home valuation at https://mcgreevyandcomisar.com/home-valuation. Office: 24031 S. Tamiami Trail, Suite 101, Bonita Springs, FL 34135. Part of Domain Realty, DomainRealtyGroup.com.