Retiring in Estero: Southwest Florida’s Hidden Gem
JESSE MCGREEVY February 18, 2026
JESSE MCGREEVY February 18, 2026
If you’ve been looking at maps of Southwest Florida trying to decide where to land, you’ve probably noticed a pattern. You have the high-energy, historic vibes of Fort Myers to the north and the upscale, luxury lifestyle of Naples to the south. Right in the middle—in what locals call the "sweet spot"—sits Estero.
For years, people drove through Estero to get to the "bigger" cities. But as we move through 2026, Estero has firmly established itself as a premier destination for retirees who want the best of both worlds. It’s a newer, master-planned village (incorporated only recently in 2014) which means the infrastructure is modern, the landscaping is manicured, and the strict design codes keep the neon signs and billboards away.
The location is strategic. You are minutes from Southwest Florida International Airport (RSW), right next to the massive Coconut Point Mall, and a short drive to the beaches. If you are looking for retirement communities in Estero FL, you aren't just buying a home; you're buying into a "village" atmosphere that feels distinct from the sprawling urbanization found elsewhere in the state.
So, why are so many active adults picking this specific zip code over the rest of the Sunshine State? Beyond the weather, it usually comes down to a mix of financial strategy and lifestyle convenience.
Let’s talk numbers first. Florida has no state income tax, which is a huge draw, but Estero sweetens the pot with one of the lowest millage rates in the area (around 0.73 mills for the Village portion). Because the village has a healthy commercial tax base from all the retail, the residential property tax burden is often lighter here than in neighboring municipalities.
Then there is the lifestyle. You don’t have to drive 30 minutes to buy a pair of shoes or get a good steak. Shopping in Estero is world-class, anchored by Coconut Point Mall and Miromar Outlets. These aren't just strip malls; they are walkable, outdoor lifestyle centers where you can grab a coffee, catch a movie, and run errands all in one loop.
Healthcare is another massive factor for retirees. The Lee Health Coconut Point facility offers a 24-hour emergency room, surgery center, and dozens of specialists right in town. While it’s not an inpatient hospital, it handles the vast majority of daily medical needs. For major procedures, NCH North Naples is just a short drive south.
Finally, you have nature. While Estero isn't directly on the beach, you have the Estero River flowing through town. You can kayak at Koreshan State Park—a fascinating historic settlement—or take a quick drive to the best beaches near Estero FL, like Lovers Key State Park.
When you start hunting for homes, you’ll notice two distinct categories. First, you have the "official" 55+ communities, where at least one resident must meet the age requirement. Second, you have "active lifestyle" communities. These are open to all ages, but because of their amenities and price points, the demographic is heavily skewed toward active adults and retirees.
Here is a breakdown of the top contenders in 2026.
If you want a social calendar that is absolutely packed, The Cascades is usually the first stop. This is a dedicated 55+ community, meaning the neighborhood is quiet, established, and focused entirely on the active adult lifestyle.
The Vibe: It’s highly social. If you play tennis or pickleball, you will find games running constantly. The atmosphere is friendly and very active.
The Homes: These are single-family homes, mostly built between 2002 and 2007. Because they are slightly older than the new builds down the street, you often get more square footage for your money. Prices generally range from the mid $400s to the $700s.
Amenities: The centerpiece is a 26,000-square-foot clubhouse. You’ve got indoor and outdoor pools, a massive fitness center, and dedicated rooms for arts, unmatched by many newer communities.
Fees: HOA fees are reasonable here, typically landing in the $350–$450/month range. This often includes high-speed internet and cable, which helps offset the cost. If you are looking for Cascades at Estero homes for sale, you are looking at one of the best values for a gated 55+ experience in the area.
For those who prefer new construction homes in Estero (or close to it), Tidewater is the modern alternative. Built by Del Webb, this community is smaller and more "boutique" than the massive developments of the past.
The Vibe: Modern, coastal, and intimate. With only about 385 homes, it’s easier to meet your neighbors here than in a community of 2,000 doors.
The Homes: Construction started around 2015, so these homes are built to newer hurricane codes. A rare bonus for Florida: many of these homes feature gas appliances, which is a huge selling point for serious cooks. Prices typically run from $500k to over $800k.
Amenities: The clubhouse feels like a resort. There is a lifestyle director on-site, a resort-style pool, a "barefoot bar" for happy hours, and a dog park.
Fees: The HOA fees are competitive, usually hovering around the $300/month mark, covering landscaping and those resort amenities.
Pelican Sound is unique because it offers "bundled golf." This means when you buy the house, the golf membership is included. There are no massive initiation fees like you’d find at private equity clubs, though you will pay annual dues.
The Vibe: This is a paradise for boaters and golfers. It is not age-restricted, but the lifestyle is heavily geared toward active retirees.
The Homes: You have a mix of everything here—condos starting in the $300k range, coach homes, and single-family estates going for $900k+.
Unique Feature: Aside from the 27 holes of golf, Pelican Sound has a private boat ramp and a shuttle boat that takes residents directly to the beaches at Lovers Key. It’s a rare perk that sets it apart from other golf course communities in Estero FL.
Fees: Be aware that because this includes golf and club access, your carrying costs are higher. Between the Master HOA and Club dues, you might be looking at $10k–$12k annually, but for unlimited golf, many residents find it a steal.
If you hate driving and love a Mediterranean flair, Rapallo might be your match. Located directly adjacent to the Coconut Point Mall, this community feels like the Italian Riviera.
The Vibe: Walkable and artistic. You can literally walk from your gate to a movie theater or a steakhouse.
Amenities: The "Club at Rapallo" is visually stunning with lagoon pools, an Olympic lap pool, a tennis program, and an arts center. It attracts a mix of full-time residents and snowbirds who want a "lock-and-leave" lifestyle.
The Homes: Mostly condos, coach homes, and courtyard villas ranging from $350k to $700k.
Retiring in Florida doesn't always have to mean million-dollar views. There are several communities that offer incredible value if you know where to look.
Villagio is a favorite for those who want a lot of amenities without a massive price tag. It’s a gated condo community that features its own "Town Center" inside the gates, complete with a cinema, café, and sports bar. Condos here often trade in the $300s, making it one of the more accessible options.
Breckenridge Golf & Tennis is another spot to watch. It offers bundled golf and tennis on a budget. The Par-3 course is perfect for seniors who want to play regularly without the exhaustion of a championship length course. It’s very social and condo-heavy.
For those strictly budgeting, Estero Bay Village offers a riverfront lifestyle at a fraction of the cost. This is a 55+ manufactured home community with boat access. You can find homes in the $200s–$300s here, allowing you to keep your nest egg liquid while enjoying the water.
If you are hunting for affordable homes in Estero FL, these three neighborhoods should be on your list.
Moving to Florida changes your budget. Some things get cheaper, and some get much more expensive. Here is the reality of the cost of living in Estero FL right now.
Home Prices: The median home price generally sits between $400k and $600k. However, this varies wildly depending on whether you are buying a condo or a single-family home with a pool.
HOA and CDD Fees: You have to watch out for two fees here.
HOA Fees: These can range from $300/month in a standard gated community to over $1,000/month in luxury bundled golf neighborhoods.
CDD Fees: Many communities in Estero have a Community Development District (CDD) fee. This is a bond paid to the local government for infrastructure (roads, sewers) put in by the developer. It usually appears on your annual tax bill and can add $1,000 to $2,000 a year to your costs. Always ask if a home has a CDD balance.
Insurance: This is the biggest variable in Florida. If you buy a home built before 2002 (new building codes), your insurance premiums could be $4,000–$6,000+ a year due to windstorm risks. Newer homes (post-2015) enjoy much lower rates, often in the $2,000–$3,000 range. Also, check the flood zone—flood insurance is separate and often mandatory here.
Taxes: The good news! If you make this your primary residence, the Florida homestead exemption explained simply is a deduction of up to $50,000 off your home's assessed value for tax purposes. Plus, it caps the annual increase of your assessed value, protecting you from tax spikes as property values rise.
Still on the fence? Here is a quick way to look at the three main markets.
Estero: This is for the golfer, the shopper, and the person who wants a calm, manicured base of operations. It is newer and quieter. Prices are mid-range.
Naples: If you want ultra-fine dining, high-end boutiques, and a very upscale feel, moving to Naples FL might be the play. However, expect to pay a premium—median prices there can be $200k higher than Estero.
Fort Myers: If you love history, a walkable downtown river district with nightlife, or need a lower price point, Fort Myers is a great option. It has more traffic and an urban feel compared to Estero's master-planned calmness.
The top contenders are usually The Cascades at Estero for a traditional, amenity-rich environment, and Tidewater by Del Webb for a modern, boutique feel. Both offer strict age-restriction protections and active social calendars.
Yes, it is consistently ranked highly for safety, tax benefits, and lifestyle. The lack of state income tax combined with access to top-tier healthcare at Lee Health and walkable shopping at Coconut Point makes it very convenient for seniors.
It varies significantly by community type. Standard gated communities typically charge between $300 and $450 per month. However, bundled golf communities will have higher monthly or annual fees to cover club memberships and course maintenance.
Estero is home to Lee Health Coconut Point, which includes a 24/7 emergency department, surgery center, and observation beds. For full inpatient hospital stays and trauma care, residents typically go to nearby NCH North Naples or Gulf Coast Medical Center.
Estero really does offer a "sweet spot" for retirement in Southwest Florida. You get the luxury and safety of a master-planned village without the extreme price tag of downtown Naples.
If you are considering a move, my best advice is to come down and see it. Drive the neighborhoods, have lunch at Coconut Point, and see if the vibe fits. Many people choose to rent seasonally for a month or two to "try on" a community before buying.
Whether you are looking for best 55+ communities in Southwest Florida or just a quiet condo near the golf course, Estero has inventory that fits almost every lifestyle. Browse the current listings, compare the fees, and get ready to enjoy the sunshine.
Stay up to date on the latest real estate trends.
Our team’s unprecedented professionalism, skill, and attention to detail has allowed us to set sales records for the past 15 years. We will ensure your buying or selling experience exceeds your expectations.