Chatham Square II is 120 condominiums in five three-floor buildings on Dennis Circle inside Glen Eagle, 119 of them with a golf membership, and the building-by-building milestone record. Sell or buy with McGreevy and Comisar.
McGreevy and Comisar are the team Chatham Square II owners call first when they are ready to sell, and the team buyers call when they want the building-level record before they tour: which of the five buildings has finished its county milestone inspection and which has not, what the three floor plans have actually sold for, what the club, the condominium and the shared Commons each charge, and what the recorded declaration says about leasing, pets and flooring. Chatham Square II is a 120-residence condominium of five three-floor buildings inside the Glen Eagle Golf & Country Club community in Naples, Florida. It sits on the north side of Dennis Circle, faces the golf course and a lake, and, with Glenmoor Greens I, is one of Glen Eagle’s two lowest-priced ways into a bundled golf membership.
Jesse McGreevy and Marc Comisar lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012 and Top 1% of agents nationally since 2008. This page is built from the recorded declaration of condominium and its 2009 restatement and 2015 amendments, the notices of commencement recorded against the five buildings since 1998, Collier County’s live milestone-inspection roster, the Florida condominium records and structural integrity reserve study database, the Collier County tax roll (2026 preliminary, unit by unit), FEMA’s effective and preliminary flood maps queried building by building, the school district’s address lookup, the club’s 2026 Realtor’s Packet, and every Chatham Square II closing in the Southwest Florida MLS for the last five years. Where the public record stops, we say so and name the document that answers the question.
If you own a Chatham Square II condo and are weighing a sale, start with the market snapshot and the seller section. If you are buying, the building-by-building milestone record and the rule-by-rule detail below will tell you whether a Chatham Square II unit fits before you drive through the Glen Eagle gate.
By Jesse McGreevy and Marc Comisar, McGreevy and Comisar, Domain Realty Group. Updated September 2026.
McGreevy and Comisar are the best realtor for Chatham Square II at Glen Eagle because the proof is on the record: the #1 team in Southwest Florida since 2012, Top 1% nationally since 2008, over $900 million in personal sales, and a Chatham Square II market read built on every closing of the last five years and the county’s building-by-building milestone roster.
If you’re searching for the best realtor for Chatham Square II in Glen Eagle Golf & Country Club, Naples, whether you’re ready to sell your Chatham Square II home or buy your next one, McGreevy and Comisar is the team that delivers. We lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 billion sold as a team and $900 million in personal sales between Jesse and Marc.
Recent Chatham Square II track record: In the last 12 months Chatham Square II has seen 4 resales in the Southwest Florida MLS (closings dated September 26, 2025 to September 26, 2026, pulled September 26, 2026): $268,000, $257,500, $210,000 and $265,000, for $1,000,500 in total sold volume. The highest-priced Chatham Square II sale in that window was $268,000, a 1,275-square-foot end unit. Because four sales are too few for a reliable median, we also measure the full five years: 13 closings from September 2021 to September 2026 at a median $295,000, a median 83 days on market and an average 96.1% of list price. The MLS pull behind this page recorded the list and sold prices, not the listing office on each closing, so we do not state a represented-sale count for Chatham Square II here; ask us and we will walk you through all 13 closings one by one.
For Chatham Square II sellers: premium marketing, including cinematic video, drone, professional photography, a qualified-buyer database, and discretion with off-market capability when a sale needs to stay quiet. At Chatham Square II we also build the paperwork file before the first showing: your building’s milestone status and the recorded repair permits, the association’s estoppel and the club’s estoppel, the working capital contribution your buyer will owe, your building’s flood zone on both FEMA maps, and the flooring and leasing rules a buyer’s attorney will read. In a building set where four of five buildings show on the county roster as behind on their milestone inspection, the seller who answers the milestone question before a lender or insurer asks it is the seller who keeps the buyer.
For Chatham Square II buyers: the first question is the building, because the building decides the milestone status: Building G has completed its inspection and is next due in 2035, while Buildings E, F, H and I show as delinquent and have Phase 2 concrete repairs permitted since September 2025. The second is the plan: 1,097, 1,209 or 1,275 square feet. The third is the bill stack, from the club’s $8,031 golf dues to the association’s own budget. Sellers and buyers comparing the best real estate agents in Naples should ask each one to answer those three questions for a specific Chatham Square II address; we answer them below.
Honors and recognition:
Selling your Chatham Square II home? Get a free Chatham Square II home valuation or call Jesse direct at (239) 898-6072.
Buying a home in Chatham Square II? Call Marc at (239) 287-5873 for a personalized buyer consultation, or read how we represent buyers in Naples.
Chatham Square II at Glen Eagle in one screen: the count, the buildings, the price, the bill stack, the flood map and the milestone law, each figure sourced below in the section that proves it.
Living in Chatham Square II at Glen Eagle means a two- or three-bedroom condominium on one of five golf-and-lake buildings on the north side of Dennis Circle, an assigned covered parking space, a shared pool and tennis court a short walk away, and the full Glen Eagle club, from the par-70 course to the fitness center, attached to the home under the club’s recorded Declaration.
Chatham Square II is one of fifteen neighborhood associations inside Glen Eagle Golf & Country Club and one of its larger condominiums by count. Of Glen Eagle’s 1,234 homes, 120 are Chatham Square II condominiums, according to the Collier County tax roll (2026 preliminary) and the Florida condominium records, which lists the condominium at 120 units. What follows is the day-to-day picture, drawn from the recorded documents and county records.
Chatham Square II, a Condominium, is a Chapter 718 condominium of 120 units in five buildings, operated by Chatham Square II, Inc., a Florida not-for-profit corporation formed on August 22, 1990. Its declaration was recorded on February 13, 1991 at Official Records Book 1592, Page 1656, and restated in full in 2009. It is not the same condominium as Chatham Square I, the 96-unit condominium that shares Dennis Circle, even though the two appear under one name, “Chatham Square”, in the Southwest Florida MLS.
Each Chatham Square II building holds 24 homes on three residential floors of eight, numbered 101 to 108, 201 to 208 and 301 to 308 on the county roll. The two end homes on each floor (01 and 08) are the 1,275-square-foot plan; the middle homes are the 1,097-square-foot plan, except the 04 and 05 positions on the second and third floors, which are the 1,209-square-foot plan. The club’s 2026 Realtor’s Packet describes Chatham Square II as one of Glen Eagle’s “3 or 4-story” building groups, and the restated Declaration lists a common utility and elevator room among the elements the association maintains.
Dennis Circle is a loop off Glen Eagle Boulevard in the east half of the community. Chatham Square II takes the north arc of the loop: Building E at 7105 and Building F at 7065 face a lake and the golf course, Building G at 7025 sits at the center of the arc, and Buildings H at 6985 and I at 6945 run east toward the fairway. Chatham Square I’s two-storey buildings take the south and west arcs. The Chatham Square pool and tennis court sit in the green inside the loop.
The owners are mostly second-home and investor buyers. The Collier County tax roll (2026 preliminary) shows a homestead exemption on 33 of the 120 Chatham Square II units, so about 28% are owner-occupied as a primary residence; 117 of the 120 tax bills mail to United States addresses and one each to Canada, Chile and the United Kingdom. The same roll puts the median Chatham Square II just value at $236,363.
Daily life at Chatham Square II is a golf-community routine at a condominium price: a covered parking space outside the building under section 8 of the restated Declaration, the Commons pool steps away, a short drive to the Glen Eagle clubhouse on Glen Eagle Boulevard, and Davis Boulevard shopping minutes past the gate. The club runs the golf course, clubhouse, dining room, fitness center, four Har-Tru tennis courts and a heated pool; the Chatham Square Commons runs the pool and tennis court inside Dennis Circle; the condominium runs the buildings.
Chatham Square II condos have sold for a median $295,000 across 13 Southwest Florida MLS closings in the last five years, and for $210,000 to $268,000 in the four closings of the last twelve months. Every recent sale closed below its final list price, and the two homes listed on September 26, 2026 ask $215,000 and $225,000.
Data updated: September 2026
We tracked every one of the 13 Chatham Square II closings in the Southwest Florida MLS from September 27, 2021 to September 26, 2026, plus the county’s recorded deeds for the same five buildings, and split them from Chatham Square I address by address (the method is in the next section). Our window rule is simple: we report the shortest window that holds at least ten closings, and under ten we list the sales instead of quoting a median. At Chatham Square II the 12-, 24- and 36-month windows hold 4, 8 and 9 closings, so the five-year window carries the headline figures and the last twelve months are listed one by one.
Four Chatham Square II homes closed in the Southwest Florida MLS between September 26, 2025 and September 26, 2026. None sold at or above its final list price; the four averaged 90.8% of list and took a median 209.5 days on market.
Closed | Building | Plan (county roll) | Sold price | Days on market | Sold as % of final list |
|---|---|---|---|---|---|
January 16, 2026 | H, 6985 Dennis Cir, unit 308 | 1,275 sq ft end unit | $268,000 | 55 | 96.1% |
February 27, 2026 | F, 7065 Dennis Cir, unit 203 | 1,097 sq ft | $257,500 | 299 | 93.7% |
April 3, 2026 | H, 6985 Dennis Cir, unit 204 | 1,209 sq ft | $210,000 | 241 | 84.7% |
June 3, 2026 | E, 7105 Dennis Cir, unit 302 | 1,097 sq ft | $265,000 | 178 | 88.6% |
Source: Southwest Florida MLS, Residential, Development GLEN EAGLE, pulled September 26, 2026; plan sizes from the Collier County tax roll (2026 preliminary). The April 2026 listing gave its living area as 1,400 square feet; the county roll records unit 204 as a 1,209-square-foot plan, and we use the county figure.
The county’s deed record adds a fifth recent sale the MLS did not carry: unit 103 in Building H recorded at $284,000 on April 9, 2026 and is marked as a qualified sale on the Collier County roll. Counting the county’s qualified sales from August 29, 2025 to August 28, 2026 instead of MLS closings, Chatham Square II recorded 6 sales at a median $266,500 ($210,000 to $284,000).
Window (to September 26, 2026) | Closings | Median | Range | Median days on market | Average sold-to-list | Closed at or above list |
|---|---|---|---|---|---|---|
12 months | 4 | listed above | $210,000 to $268,000 | 209.5 | 90.8% | 0 |
24 months | 8 | $274,000 | $210,000 to $350,000 | 144.5 | 94.0% | 1 |
36 months | 9 | $280,000 | $210,000 to $350,000 | 122 | 94.1% | 1 |
60 months | 13 | $295,000 | $210,000 to $385,000 | 83 | 96.1% | 5 |
Medians are the middle sale (for an even count, the mean of the middle two); sold-to-list is the average of each sale’s own ratio. Total five-year sold volume was $3,819,000, and the median five-year price per square foot of MLS living area was $268.92. The top Chatham Square II sale of the five years was $385,000, a 1,209-square-foot unit on the third floor of Building F in June 2022.
Two Chatham Square II homes were listed for sale in the Southwest Florida MLS on September 26, 2026, both the 1,097-square-foot two-bedroom plan: unit 107 in Building I at $225,000 (255 days on market) and unit 202 in Building G at $215,000 (211 days on market). No Chatham Square II listing was pending that day. Against 4 closings in twelve months, two listings is roughly six months of supply.
Plan decides price at Chatham Square II more than any other feature. In the five-year MLS record the 1,275-square-foot end units closed at $268,000 and $350,000, the 1,209-square-foot units at $210,000, $280,000 and $385,000, and the 1,097-square-foot interior units at $257,500 to $319,000. Floor matters less than you might expect: third-floor units sold at both the top ($385,000) and near the bottom ($265,000) of the range, because timing and condition moved prices more than elevation did.
Chatham Square II followed the Naples condominium cycle. The four 2021 and 2022 closings all sold at or above list, at $280,500 to $385,000, with a median of 6.5 days on market. From 2024 on, sales took longer and closed lower: the 2025 closings ranged from $280,000 to $350,000, and the four closings of 2026 to date sit between $210,000 and $268,000. The same pattern shows in the county’s deed record, where the Chatham Square II median qualified sale fell from $300,000 across the three qualified sales of September 2021 through 2022 to $266,500 in the twelve months to August 2026.
Chatham Square II sits at Glen Eagle’s entry price. Across all 15 Glen Eagle neighborhoods the Southwest Florida MLS recorded 63 sales at a median $405,000 in the twelve months to September 24, 2026. Chatham Square II’s own four sales in the same span all closed at $268,000 or less, and its five-year median of $295,000 is the second lowest among Glen Eagle’s condominiums in the five-year MLS table, above only Glenmoor Greens I at $272,500 (16 closings) and below Saratoga Colony at $364,000, Glenmoor Greens II at $440,000 (12 closings), Sterling Greens at $365,000 and the Sterling Lakes condominiums at $422,500 to $430,000. The comparable-subdivisions section below lays the full table out.
For buyers, 2026 is a buyer’s market at Chatham Square II: every recent sale closed below list, the median sale of the last year sat almost seven months, and the milestone repairs give a careful buyer room to negotiate. For sellers, the months from November to April bring the seasonal buyers who own most of Chatham Square II, and a listing priced to the two current asks and documented on the milestone question competes on the right terms. We tell both sides the same thing: the building file matters as much as the price.
Thinking about Chatham Square II at Glen Eagle? Ask us for the building file before you tour: which building has completed its milestone inspection, which units in Buildings E, F, H and I sit on the recorded Phase 2 repair notices, and what the three plans have sold for. Buyers: call Marc at (239) 287-5873 or read how we represent buyers in Naples. Sellers: call Jesse direct at (239) 898-6072 or get a free Chatham Square II home valuation.
Chatham Square II and Chatham Square I share one Southwest Florida MLS subdivision name, “CHATHAM SQUARE”, so a search for Chatham Square returns both condominiums mixed together. We split every row by street number against the Collier County tax roll, where each Dennis Circle address carries its own condominium number and building letter.
The county roll is unambiguous. Every parcel at 6945, 6985, 7025, 7065 and 7105 Dennis Circle belongs to Chatham Square II (120 units), and every parcel at 6700, 6740, 6780, 6820, 6860, 6900, 7145 and 7185 Dennis Circle belongs to Chatham Square I at Glen Eagle (96 units). Of the 35 Chatham Square closings in the MLS over five years, 13 are Chatham Square II and 22 are Chatham Square I.
Street number on Dennis Circle | Building | Condominium | Homes | Floors |
|---|---|---|---|---|
7105 | E | Chatham Square II | 24 | three |
7065 | F | Chatham Square II | 24 | three |
7025 | G | Chatham Square II | 24 | three |
6985 | H | Chatham Square II | 24 | three |
6945 | I | Chatham Square II | 24 | three |
6700, 6740, 7185, 7145 | A, B, C, D | Chatham Square I | 12 each | two |
6900, 6860, 6820, 6780 | J, K, L, M | Chatham Square I | 12 each | two |
Two shortcuts help. A Chatham Square unit number in the 300s is always Chatham Square II, since Chatham Square I buildings have two floors. A Chatham Square address listed at 1,308 square feet is almost always Chatham Square I, whose 96 homes are all that one plan on the county roll. When a listing’s own square footage disagrees with the county, as happens on a few Chatham Square rows, we go with the county’s recorded plan.
Chatham Square II was built by Chatham Square Development Corporation in 1991 and 1992, in the first wave of the Embassy Woods Golf and Country Club at Bretonne Park community that was renamed Glen Eagle in 1998. Its declaration was recorded on February 13, 1991, the buildings followed through early 1992, and by 1993 the owners’ association was in Collier circuit court against the developer (case 93-4692-CA), a case closed by judgments recorded in 1997.
The community around Chatham Square began in 1990 as Embassy Woods Golf and Country Club at Bretonne Park, with a Mark McCumber course that opened in 1991. The master association was renamed Glen Eagle Golf & Country Club, Inc. in amended and restated articles filed with the state on January 20, 1998, and the members elected an entirely owner-controlled board on August 2, 2004, according to the club’s own history and the articles of amendment filed that September. The Florida condominium records still lists both Chatham Square condominiums at “Chatham Square Lane, Naples 33962”, the pre-rename street name and ZIP.
Chatham Square Development Corporation formed all three Chatham Square associations on August 22, 1990: Chatham Square I, Inc., Chatham Square II, Inc., and the Chatham Square Commons Association, Inc., which holds and runs the shared pool, tennis court, roads and parking inside Dennis Circle. The Commons declaration was recorded on September 13, 1990 at Official Records Book 1558, Page 1174, five months before the Chatham Square II declaration.
The original Chatham Square II declaration was recorded on February 13, 1991 at Official Records Book 1592, Page 1656 (82 pages), with Capital Bank joining in the instrument. A run of surveyor’s certificates and amendments recorded from September 1991 to April 1992 added the buildings as they were completed. The Florida condominium records records the same February 13, 1991 date and 120 units. On April 16, 2009 the owners adopted a full amended and restated Declaration, recorded July 23, 2009 at Official Records Book 4474, Page 3011, which governs today with two recorded 2015 amendments.
The county tax roll gives Buildings E, F and G a 1991 year built and Buildings H and I a 1992 year built. Collier County’s list of milestone buildings gives certificates of occupancy of March 28, 1991 for Building E, September 10, 1991 for Building G and January 14, 1992 for Buildings H and I. Every Chatham Square II building therefore passed 25 years of age in 2016 or 2017, which is why the county’s milestone deadline for all five was December 31, 2024.
Chatham Square II has three floor plans on the Collier County tax roll: a 1,097-square-foot interior plan, a 1,209-square-foot plan on the second and third floors, and a 1,275-square-foot end plan. Each building repeats the same layout, so a buyer can identify the plan from the unit number alone.
Plan (county base area) | Where in each building | Homes per building | Homes in Chatham Square II | How the MLS usually lists it |
|---|---|---|---|---|
1,097 sq ft | 102 to 107; 202, 203, 206, 207; 302, 303, 306, 307 | 14 | 70 | two bedrooms, two baths |
1,209 sq ft | 204, 205, 304, 305 | 4 | 20 | two bedrooms, two baths |
1,275 sq ft | 101, 108, 201, 208, 301, 308 | 6 | 30 | three bedrooms (or two plus den), two baths |
Plan sizes and positions are from the Collier County tax roll (2026 preliminary), unit by unit; bedroom counts are from the MLS listings and vary with how each owner describes the third room. No Chatham Square II plan appears in the county roll at a size other than these three.
The restated Declaration gives every Chatham Square II unit the exclusive use of at least one assigned covered parking space as a limited common element. The carports are the association’s to maintain, and the Declaration lets two owners swap assigned spaces by written agreement with the board’s approval. Carport work was recorded under notices of commencement in November 1998 for Carports A to D (Aluminum Specialties) and in 2006 for carport and Building F work (Stettinus Construction).
The two ends of every floor are the larger plan and have windows on three sides. Buildings E and F look north over a lake toward the golf course; Buildings G, H and I look out over the fairway on the north and east sides of the circle. Ground-floor homes step straight out to the lawn; third-floor homes have the longest views.
A Chatham Square II condo comes with three layers of amenities: the unit and its covered parking space from the condominium, a shared pool, tennis court, roads and parking from the Chatham Square Commons, and the full Glen Eagle club, including golf, from the membership the club’s recorded Declaration exhibit attaches to 119 of the 120 units.
Layer | Who runs it | What it covers for a Chatham Square II owner | Recorded source |
|---|---|---|---|
The unit | The owner | Interior, floor coverings, screens, sliding doors, the unit’s own air conditioning | Restated declaration, sections 8 and 11 |
The condominium | Chatham Square II, Inc. | Five buildings: exterior walls, concrete slabs and walkways, the utility and elevator room, lanai and walkway railings, carports, fire alarm and sprinkler systems, pipes and wiring up to each unit | Restated declaration, sections 8 and 11.1 |
The Commons | Chatham Square Commons Association, Inc. | Pool, tennis court, roads, parking areas and retention areas shared with Chatham Square I | Commons declaration, OR 1558 PG 1174 |
The club | Glen Eagle Golf & Country Club, Inc. | Golf course, clubhouse, dining, fitness center, club tennis courts and pool, gatehouse and private roads | Club declaration and 2026 Realtor’s Packet |
The Chatham Square Commons Association was created to own and run the recreation facilities, roads, parking and water management shared by the two Chatham Square condominiums; its articles name swimming pools, tennis courts, a bathhouse, common roads and covered and open parking among its purposes. Recorded notices show the pool deck extended in 2004 (Liberty Concrete and Masonry) and pool-area work in 2010 (Hegi Construction). In 2016 the Commons won a circuit-court judgment (case 16-CA-1195) quieting its title to the Commons land against the dissolved original developer. The Commons rules bar pets from the pool, and the restated condominium declaration repeats the rule.
Golf is included with 119 of the 120 Chatham Square II units. The club’s recorded “Designation of Membership” exhibit, in the 2015 Amended and Restated Master Declaration and Bylaws, lists Chatham Square II at 119 golf and 1 social membership. A golf membership covers the par-70, 18-hole Mark McCumber course that opened in 1991, with cart fees of $26.50 per 18 holes in 2026; a social membership covers every non-golf facility and golf from May through October. The membership belongs to the unit and cannot be bought, sold or upgraded separately, according to the club’s 2026 Realtor’s Packet.
The Glen Eagle clubhouse holds a dining room, private dining room, lanai, the 19th Hole lounge, a fitness center, billiard and card rooms, a meeting room and an activities center, and the club adds four lighted Har-Tru tennis courts and a heated pool, according to the club’s amenities page and its 2026 packet. Every Chatham Square II owner pays a $600 annual food and beverage minimum. There is no marina, beach club or pickleball court inside Glen Eagle; East Naples Community Park, home of the US Open Pickleball Championships, is the nearest large pickleball venue.
Chatham Square II owners pay three recurring bills: Glen Eagle club dues of $8,031 a year for the 119 golf units in 2026, the Chatham Square II association’s own assessment (which also carries the unit’s share of the Chatham Square Commons budget), and the club’s $600 food and beverage minimum. The condominium’s budget and quarterly assessment are not published.
Bill | Amount | How often | Source |
|---|---|---|---|
Glen Eagle golf membership dues | $8,031 a year (2026) | half on January 1, half on July 1 | Club 2026 Realtor’s Packet |
Glen Eagle social membership dues (one unit) | $5,402 a year (2026) | half on January 1, half on July 1 | Club 2026 Realtor’s Packet |
Club food and beverage minimum | $600 a year | calendar year, not prepaid | Club 2026 Realtor’s Packet |
Chatham Square II condominium assessment | not published; set in the association’s annual budget | monthly or quarterly, as the board decides under the bylaws | Restated declaration and bylaws |
Chatham Square Commons share | included in the condominium’s budget; Chatham Square II carries 120 of the 216 Chatham Square homes, about 55.6% of the Commons budget | billed quarterly to the association | Commons declaration, section 7 |
Property taxes | millage code 266, 10.6058 mills in 2025; the county’s 2026 preliminary roll computes a median of about $2,277 per Chatham Square II unit | annual | Collier County Tax Collector and tax roll |
Community development district | none | none | County CDD layer and state special district list |
The club’s dues nearly doubled over ten years: golf dues were $4,078 in 2016 and are $8,031 in 2026, according to the club’s archived 2016 Sale Information Packet and its 2026 packet. The condominium’s own budget, reserve schedule and any special assessment are held by the association’s manager and are not public; a buyer under contract receives them with the resale disclosure documents.
Cost at closing | Amount | Paid by | Source |
|---|---|---|---|
Club Resale Capital Contribution (golf unit) | $9,000 | buyer | Club declaration Article 11.12(B); 2026 packet |
Club Resale Capital Contribution, buyer already a Glen Eagle owner | $4,500 (golf) | buyer | 2026 packet |
Club transfer fee | $425 (golf), $350 (social) | per contract | 2026 packet |
Club estoppel certificate | $299, or $399 if needed in under five business days | per contract | 2026 packet |
Chatham Square II working capital contribution | set by the board, capped at $1,000 | buyer | Declaration section 14.7 as amended December 7, 2015 |
Association estoppel and application fees | set by the association within Florida’s statutory caps | per contract | Florida Statutes sections 718.116 and 718.112 |
A buyer of a golf unit therefore brings up to $10,000 in capital and working capital contributions to closing, on top of the price, before the estoppel and transfer fees.
Fees are where Chatham Square II buyers most often get surprised. Selling a Chatham Square II condo? Get a free Chatham Square II home valuation or call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Chatham Square II is governed by four layers: its own condominium association, Chatham Square II, Inc., under Chapter 718; the Chatham Square Commons Association for the shared pool, roads and parking; the Glen Eagle master association and club under Chapter 720; and Collier County for building safety, including the milestone inspection program.
Chatham Square II, Inc. is a Florida not-for-profit corporation filed on August 22, 1990 (Florida Division of Corporations document N39621). The Florida condominium records lists it as the managing entity of Chatham Square II, a Condo (project PR1S021416), care of Anchor Associates, Inc., 2340 Stanford Court, Naples, in the state’s condominium public records extract read September 26, 2026. The club’s 2026 packet lists Anchor Associates (239-649-6357) as the manager for both Chatham Square condominiums and the Chatham Square Commons.
Chatham Square Commons Association, Inc. (document N39623, filed the same day in 1990) has two members, Chatham Square I, Inc. and Chatham Square II, Inc. Its board adopts a budget each December and assesses each condominium in proportion to its share of the 216 Chatham Square homes, billed quarterly on the first of January, April, July and October; each condominium then passes its share through to its owners, under section 7 of the Commons declaration.
Glen Eagle Golf & Country Club, Inc. is both the master homeowners’ association and the club, owned by the 1,234 Glen Eagle homeowners (document N39323). Every Chatham Square II owner is a member of both the master association and the condominium association, and the club’s packet notes that neighborhood rules “could have more strict rules than the Master Association, however, they can never have less strict rules.”
The Chatham Square II declaration of condominium was restated in full in 2009 and amended twice in 2015, and it sets rules that are stricter than most Glen Eagle neighborhoods on leasing, guests and pets. The recorded instruments and their key sections are summarized below; the full text is public at the Collier Clerk.
Instrument | Recorded | What it does |
|---|---|---|
February 13, 1991, OR 1592 PG 1656 | Creates the condominium (82 pages) | |
January 2007, OR 4166 PG 2519 | Cuts leases to three a year, none longer than three months | |
July 23, 2009, OR 4474 PG 3011 | Restates the whole declaration; adopted April 16, 2009 | |
June 19, 2012, OR 4808 PG 2209 | Buys flood insurance only if required by law; authorizes a Letter of Map Amendment | |
August 26, 2015, OR 5188 PG 1790 | Drops the wall-to-wall carpet rule; hard floors need a sound rating of 68 and board approval | |
December 7, 2015, OR 5221 PG 242 | Raises the buyer’s working capital contribution cap from $400 to $1,000 |
Every sale or gift needs the board’s prior written approval under section 14 of the restated Declaration. The seller gives the board at least 20 days’ notice before closing with the buyer’s name and the signed contract, the board may interview the buyer, and it must approve or disapprove within 20 days after receiving everything (or 60 days after the notice, whichever comes first). Approval can be withheld only for listed good-cause reasons; if the board disapproves without good cause and the owner has made a written demand, the association must supply an approved alternate purchaser at the same price and terms. A sale closed without approval is voidable, and the board may suspend a real estate agent or company that skips the procedure after one written warning.
Since the August 2015 amendment, Chatham Square II no longer requires wall-to-wall carpeting: hard flooring is allowed anywhere in the unit, including bedrooms, if a licensed contractor installs it over an underlayment that meets a sound transmission class rating of 68 (the amendment names Proflex 90 or equivalent as preferred) and the board approves it in writing first. Hurricane shutters must match the model, style and color the board adopts under section 11.13, and the board may not refuse a conforming shutter. Lanais may not be enclosed, tiled or carpeted without written board approval. The restated Declaration also carries a “High-Risk Components” schedule (water heaters, shut-off valves, supply lines, the air-conditioning condensate line, toilet gaskets and shower valves) with required replacements, and it requires any unit left empty for a month or longer to have a condo watcher inspect it at least monthly, with a current key on file with the association.
The restated Declaration bars “For Sale”, “For Rent” and “Open House” signs anywhere on the condominium property, including windows, lanais and vehicles. Glen Eagle’s own sign procedure, printed in the club’s 2026 packet, allows the club’s open-house signs at the entrance on weekends from noon to 4 p.m. and specifically lets a listing agent mark the open unit number in front of “3 or 4-story buildings within Sterling Greens or Chatham 2.”
Chatham Square II is not a 55+ community. Neither the restated Declaration nor the club’s documents register it as housing for older persons, and the Declaration’s occupancy rules speak of families with children, requiring only that residents under 18 be supervised by an adult. Buyers of any age may purchase, subject to the association’s approval process.
Chatham Square II allows rentals only as short seasonal leases: under section 13.2 of the restated Declaration, no unit may be leased more than three times a calendar year, for a minimum of one month and a maximum of three months, and no more than three months a year to the same tenant. Annual leases are not allowed, and every lease needs board approval.
In practice, Chatham Square II is a seasonal-rental building: a January-to-March winter lease fits the rules exactly, and a year-round tenant does not. Tenants reach Glen Eagle’s club facilities by registration and pay the club’s tenant golf rates ($75 for 18 holes from January to March in 2026, per the club’s fee schedule). Florida law protects owners on one point: under section 718.110(13) of the Florida Statutes, a rental amendment adopted after an owner bought applies to that owner only if the owner voted for it, so an owner who has held a unit since before the 2006 amendment may have different rights. Ask the association for the current rental rules and the owner’s history before you buy for rental income.
Chatham Square II owners may keep one domesticated dog or one domesticated cat weighing 30 pounds or less at maturity, plus up to two birds and tropical fish, under section 12.6 of the restated Declaration. Tenants and guests may not keep pets, and the board may remove a pet it finds to be a nuisance on three days’ notice.
Rule | Chatham Square II restated Declaration, section 12.6 |
|---|---|
Number and size | one dog or one cat, 30 pounds or less at maturity; up to two birds and tropical fish |
Tenants and guests | no pets |
Pool area | no pets, leashed or not |
Common elements | on a handheld leash or carried |
Lanais | pets may not be left unattended on screened porches or balconies |
Nuisance | written notice, removal within three days |
Exceptions | the board may grant individual exceptions with conditions |
Service and support animals are governed by federal and Florida fair housing law, not by the pet limit.
Chatham Square II is subject to Florida’s milestone inspection and structural integrity reserve study laws because its five buildings have three habitable floors. On September 26, 2026, Collier County’s milestone roster listed Building G as completed, next due in 2035, and Buildings E, F, H and I as “Milestone Delinquent”, with Phase 2 concrete repairs permitted and recorded in September 2025.
The milestone law, section 553.899 of the Florida Statutes, requires a structural inspection of every condominium building of three or more habitable stories once it reaches a set age and every ten years after. Collier County applies a 25-year trigger to buildings within three miles of saltwater, and Glen Eagle falls inside that buffer on the county’s own map. For coastal buildings with a certificate of occupancy before July 1, 1997, which includes all five Chatham Square II buildings, the county set the first-inspection deadline at December 31, 2024, according to Collier County’s milestone inspection program page.
Building | Address | County milestone status (September 26, 2026) | Next inspection year shown | County record |
|---|---|---|---|---|
E | 7105 Dennis Cir | Milestone Delinquent | 2023 | PL20230004784 |
F | 7065 Dennis Cir | Milestone Delinquent | 2023 | PL20230004783 |
G | 7025 Dennis Cir | Milestone Completed | 2035 | PL20230004785 |
H | 6985 Dennis Cir | Milestone Delinquent | 2023 | PL20230004788 |
I | 6945 Dennis Cir | Milestone Delinquent | 2023 | PL20230004789 |
Source: Collier County MilestoneMap service, milestone points layer, queried September 26, 2026. The same layer lists no Chatham Square I building, because Chatham Square I’s buildings have two floors.
A milestone inspection has two phases. Phase 1 is an engineer’s or architect’s visual inspection; if it finds substantial structural deterioration, a Phase 2 inspection with testing follows, then a repair permit within 150 days and repairs begun within 365 days, under the county’s published process. On September 26, 2025, Chatham Square II, Inc. recorded four notices of commencement for concrete work by JR Florida Builders, LLC, three of them labeled “Milestone” and “Phase 2” with the building’s county record number:
Building | Recorded work (notice of commencement, September 26, 2025) | County permit |
|---|---|---|
E, 7105 Dennis Cir | Repair the exterior concrete wall at units 303, 306 and 308 per the engineering instructions | PRMFH20250832950, OR 6511 PG 2095 |
F, 7065 Dennis Cir | Repair the concrete at unit 302; “Milestone, Phase 2, PL20230004783” | PRMFH20250832045, OR 6511 PG 2097 |
H, 6985 Dennis Cir | Repair the exterior concrete wall at unit 303; “Milestone, PL20230004788, Phase 2” | PRMFH20250832967, OR 6511 PG 2094 |
I, 6945 Dennis Cir | Repair the exterior concrete wall at units 201, 205 and 207; “Milestone, PL20230004789, Phase 2” | PRMFH20250832963, OR 6511 PG 2096 |
Our reading, labeled as ours: the “Delinquent” flag on Buildings E, F, H and I means the county’s milestone cycle for those buildings is still open past its deadline; it is not, by itself, a finding that a building is unsafe, and the recorded Phase 2 permits show the repair stage under way a year before this page was written. The engineer’s reports, the county’s letters and any occupancy letter sit in the Documents and Images tab of each record on Collier County’s GMCD public portal; a buyer should read them, and the association’s plan and budget for finishing the work, before the inspection period ends.
Florida also requires every condominium with a building of three or more habitable stories to complete a structural integrity reserve study and fund the reserves it sets, under section 718.112 of the Florida Statutes. The 2025 condominium law, CS/CS/HB 913, moved the deadline to complete a first SIRS to December 31, 2025 and applied the rule to buildings of three habitable stories or more, according to the Florida Senate bill summary. The state’s SIRS reporting database of studies submitted in July 2025 or later did not list Chatham Square II when we searched it on September 26, 2026; the state’s separate list of earlier submissions did not load in a searchable form for us. We therefore state no SIRS status for Chatham Square II; the completed study, if any, is an official record the association must provide to owners and, through the resale disclosure, to buyers.
Two costs follow from these laws: the milestone repairs themselves, and SIRS reserves that owners can no longer waive for the structural items the study covers. Either can arrive as a special assessment or a higher quarterly assessment. We have seen no public record of a Chatham Square II special assessment amount, and we do not guess one; the association’s estoppel certificate must disclose any assessment due, under section 718.116 of the Florida Statutes.
Under section 718.503 of the Florida Statutes, a resale buyer receives the Declaration, articles, bylaws, rules, the current year’s budget and financial report, the governance form, and the inspector-prepared summaries of any milestone inspection and structural integrity reserve study, and may cancel within the statutory review period after receiving them. HB 913 extended that review period for resale buyers from three days to seven, per the Senate summary. At Chatham Square II those summaries are the most important papers in the package.
The milestone file is the first thing we assemble for a Chatham Square II client. Selling a Chatham Square II condo? Get a free Chatham Square II home valuation or call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Chatham Square II’s recorded notices of commencement show the association working on its concrete in three waves, in 2001, 2012 and 2025, plus carport, fire-safety and exterior work between them. The table below lists every association notice we found in the Collier Clerk’s index, by party name, from 1998 to 2026.
Recorded | Work | Contractor | Record |
|---|---|---|---|
November 16 and 17, 1998 | Carports A to D; Building F carports 5 to 8 | Aluminum Specialties | OR 2481 PG 128 and following pages |
June 30, 2000 | Buildings H and I (scope not stated in the index) | Aluminum Specialties | OR 2693 PG 759 to 760 |
August 20, 2001 | Four notices (scope not legible in the index) | Liberty Concrete and Masonry | OR 2878 PG 1340 to 1343 |
May 2006 | Building F and carport work | Stettinus Construction | OR 4032 PG 1136; OR 4042 PG 1628 |
July 24, 2012 | “Concrete Repairs and Sealant” at all five buildings | Spectrum Contracting | OR 4819 PG 3318 to 3322 |
December 30, 2014 and July 14, 2016 | Fire and life safety work | Superior Fire and Life Safety | |
May 18, 2018 | Handwritten notice, scope not legible | Richard Minnick LLC | OR 5511 PG 1168 |
September 26, 2025 | Milestone Phase 2 concrete wall repairs, Buildings E, F, H and I | JR Florida Builders | OR 6511 PG 2094 to 2097 |
We found no recorded roof-replacement notice for Chatham Square II in the association’s party index. Roof age matters to a buyer’s insurer; ask the association for the roof dates and permits for your building.
Chatham Square II’s five buildings are in FEMA Zone X, outside the high-risk flood zone, on both the effective 2024 flood map and the preliminary map now in its appeal period, and the complex is in Collier County evacuation Zone C. The buildings predate Florida’s statewide building code, which shapes wind insurance more than flood does.
Building | Effective FEMA zone (panel 12021C0413J, effective February 8, 2024) | Preliminary FEMA zone (issued March 20, 2025) |
|---|---|---|
E, 7105 Dennis Cir | X, minimal flood hazard | X, minimal flood hazard |
F, 7065 Dennis Cir | X, minimal flood hazard | X, minimal flood hazard |
G, 7025 Dennis Cir | X, minimal flood hazard | X, minimal flood hazard |
H, 6985 Dennis Cir | X, minimal flood hazard | X, minimal flood hazard |
I, 6945 Dennis Cir | X, 0.2% annual chance (shaded X) | X, 0.2% annual chance (shaded X) |
Source: FEMA National Flood Hazard Layer and FEMA preliminary flood hazard data, queried at each building’s county address point on September 26, 2026. A narrow Zone AE strip follows the lake edge within about 40 meters of Building F’s address point on the effective map; a lender that maps the building footprint rather than the address point may ask about it. The 2012 amendment to the Chatham Square II declaration authorizes the board to seek a FEMA Letter of Map Amendment for exactly this reason. Collier County opened the appeal period on the preliminary maps on August 19, 2026 and expects them to take effect in summer 2027, per the county’s August 2026 release.
Chatham Square II is in evacuation Zone C on Collier County’s hurricane evacuation zone layer, queried at Chatham Square Buildings A and E on September 26, 2026. Hurricane Ian’s peak storm tide in Naples Bay was about 7.1 feet, according to the National Hurricane Center’s Ian report, and the ground at Glen Eagle homes sits at roughly 10.6 to 12.3 feet on the USGS elevation data our Glen Eagle research sampled. We found no public report of storm-surge flooding at Chatham Square in Irma, Ian, Helene or Milton.
The Chatham Square II buildings were finished in 1991 and 1992, a decade before the statewide Florida Building Code took effect on March 1, 2002, so they were not built to today’s wind-borne debris rules. The association insures the buildings (the condominium’s master policy, under section 718.111 of the Florida Statutes); owners carry an HO-6 policy for the interior, finishes and contents. The restated Declaration lets the board adopt one standard hurricane shutter and bars it from refusing a conforming one, and a wind mitigation report on the unit’s openings can lower an owner’s HO-6 premium. Because the buildings are in Zone X, flood insurance is optional for most lenders; Citizens Property Insurance is phasing in a requirement that its policyholders carry flood coverage, under its flood rules, so an owner insured through Citizens should check the date that applies to the unit.
Every Chatham Square II address is zoned to Calusa Park Elementary, East Naples Middle and Lely High School for the 2026-27 school year, according to the Collier County Public Schools address lookup queried for 7105 and 6945 Dennis Circle on September 26, 2026.
School | Grades | Address | 2026 state grade |
|---|---|---|---|
K to 5 | 4600 Santa Barbara Blvd | A | |
6 to 8 | 4100 Estey Ave | A | |
9 to 12 | 1 Lely High School Blvd | B |
Grades are from the district’s 2026 Accountability Brief, dated July 1, 2026. Private options within a short drive include Seacrest Country Day School at the Glen Eagle Boulevard and Davis Boulevard corner, St. John Neumann Catholic High School and the Community School of Naples.
The largest project near Chatham Square II is Vitano, a proposed community of about 622 homes and a Whole Foods Market on 82 acres at the southeast corner of Davis Boulevard and Santa Barbara Boulevard, roughly half a mile from Glen Eagle. Road work on Davis Boulevard and at the I-75 and Collier Boulevard interchange is also planned or under way.
Daily logistics at Chatham Square II run through three sets of rules: the club’s gate and vehicle rules for Glen Eagle as a whole, the Commons for Dennis Circle’s roads and parking, and the condominium for the buildings and carports.
Topic | How it works at Chatham Square II | Source |
|---|---|---|
Gate | Staffed gatehouse at the Glen Eagle Boulevard entrance on Davis Boulevard; the club bars posting its gate codes | Club 2026 packet |
Parking | One assigned covered space per unit; no motor vehicle parks except in designated areas; non-residents may not leave a car on the property or in Commons parking more than 24 hours | Restated declaration, sections 8 and 12.7 |
Vehicles | The master association bars boats, trailers, campers, motor homes, pickup trucks and commercial vehicles unless garaged (SUVs exempt) | Club disclosure summary, item 11 |
Golf carts | No owner may keep a private golf cart in any Glen Eagle neighborhood | Club declaration, section 7 |
Pets | One dog or cat of 30 pounds or less, owners only | Restated declaration, section 12.6 |
Absent owners | A condo watcher at least monthly for any unit empty a month or longer; a key on file | Restated declaration, section 11 |
Taxes | Collier County, millage code 266; no community development district | Collier County Tax Collector |
Manager | Anchor Associates, 239-649-6357 | Club 2026 packet |
From the Glen Eagle entrance on Davis Boulevard, Fifth Avenue South in downtown Naples is about 4.9 miles and 11 minutes, Naples Airport about 3.7 miles and 9 minutes, the I-75 interchanges at exits 101 and 105 about 3.6 miles and 8 minutes, and Southwest Florida International Airport about 30 miles and 40 minutes, by free-flow road routing measured for our Glen Eagle guide. The nearest supermarkets are the Publix stores at Kings Lake Square and Berkshire Commons, two to three minutes from the gate, and NCH Baker Hospital is about 5.8 road miles away.
Chatham Square II is the second lowest-priced condominium in Glen Eagle on a five-year Southwest Florida MLS median: $295,000 across 13 closings, above Glenmoor Greens I at $272,500 across 16 closings and below every other condominium neighborhood, which run from $364,000 to $440,000. It is also one of only three Glen Eagle condominium groups with buildings of three or more floors, and the only one with buildings flagged delinquent on the county’s milestone roster.
The yardstick below is the same for every row: Southwest Florida MLS closings from September 27, 2021 to September 26, 2026, pulled September 26, 2026, with Chatham Square split into its two condominiums by address. Milestone status is from Collier County’s roster on the same day.
Glen Eagle condominium | Homes | Floors | 5-year MLS closings | 5-year median | Median days on market | Average sold-to-list | County milestone status |
|---|---|---|---|---|---|---|---|
Chatham Square II | 120 | three | 13 | $295,000 | 83 | 96.1% | 1 completed (next 2035), 4 delinquent |
96 | two | 22 | $360,000 | 19 | 97.0% | not listed (two floors) | |
95 | three to four | 25 | $365,000 | 31 | 97.7% | open, not yet due (2028 to 2029) | |
120 | not on roster | 31 | $364,000 | 15 | 99.4% | not listed | |
72 | On roster | 16 | $272,500 | n/a | n/a | Completed (next 2033) | |
84 | Not on roster (two-story) | 12 | $440,000 | n/a | n/a | Not required | |
132 | not on roster | 29 | $422,500 and $430,000 | 6 and 25 | 99.2% and 97.0% | not listed |
Sterling Lakes figures are shown separately for the two MLS names, “STERLING LAKES” (14 closings) and “STERLING LAKES II” (15 closings). Glenmoor Greens I and II share one MLS name; we split their closings by street address against the county roll (1001, 1051 and 1100 Eastham Way are Glenmoor Greens I). Home counts are from the Collier County tax roll (2026 preliminary).
The pattern is plain: the three-floor Chatham Square II buildings with open milestone work trade at a discount of $55,000 to $135,000 to the rest of Glen Eagle’s condominiums on the five-year median, and they take longer to sell. For a buyer who reads the milestone file and budgets for the work, that discount is the opportunity; for a seller, it is the reason documentation matters.
Chatham Square II and Chatham Square I share Dennis Circle, a pool and tennis court, a manager and one MLS name, but they are different buildings under different rules. Chatham Square II is three-floor living at a lower price with open milestone work and seasonal-only leasing; Chatham Square I is two-floor living with garages, a single larger plan, no milestone obligation and year-round leasing.
Question | Chatham Square II | Chatham Square I |
|---|---|---|
Homes and buildings | 120 homes in 5 buildings of 24 | 96 homes in 8 buildings of 12 |
Floors | three | two |
Floor plans (county roll) | 1,097, 1,209 and 1,275 sq ft | one plan, 1,308 sq ft (two bedrooms plus den in most listings) |
Parking | one assigned covered carport space | an assigned garage plus the space in front of it |
Milestone inspection | required; Building G completed, Buildings E, F, H and I delinquent with Phase 2 repairs permitted | not required (two-floor buildings are not on the county roster) |
Structural integrity reserve study | required for three-floor buildings | not required for buildings under three habitable stories |
Leasing | one to three months, at most three leases a year | 30 days to one year, at most four leases a year |
Pets | one dog or cat, 30 lb or less, owners only | one dog or cat, 30 lb or less, owners only |
Hard flooring | allowed with board approval, sound rating 68 | allowed with board approval, sound rating 58 |
Buyer’s working capital contribution | set by the board, up to $1,000 | set by the board |
Golf memberships | 119 golf, 1 social | 96 golf |
5-year MLS median | $295,000 (13 closings) | $360,000 (22 closings) |
Last 12 months | 4 closings, $210,000 to $268,000 | 5 closings, median $310,000 |
County median just value, 2026 | $236,363 | $271,052 |
Choose Chatham Square II if you want one of the two lowest prices of entry into a Glen Eagle golf membership, a third-floor view, a smaller plan or an end unit, and you are comfortable reading a milestone file and budgeting for the repair cycle. Choose Chatham Square I if you want a garage, a larger single plan, a two-floor building outside the milestone and SIRS laws, or the flexibility to lease for up to a year.
Not sure which side of Dennis Circle fits? Selling a Chatham Square II condo? Get a free Chatham Square II home valuation or call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Owning at Chatham Square II trades a low entry price and a golf membership bundled under the club Declaration for three-floor condominium obligations under Florida’s post-Surfside laws and a strict seasonal leasing rule. Both lists below come from the recorded documents and the county’s records, not from marketing.
On Chatham Square II showings, the same three questions come up before a buyer asks about the kitchen: which building is this, has that building finished its milestone inspection, and what will the repairs cost the owners. Those three questions decide whether a lender and an insurer will close the loan, and whether the buyer stays.
As Top 1% Real Estate Agents Nationally Since 2008, we prepare for them the same way on every Chatham Square II listing. We pull the building’s status from Collier County’s milestone roster, the recorded Phase 2 repair notices, the building’s zone on both FEMA maps, and the association’s current budget and estoppel through the owner, and we put them in the listing package. We tell buyers that the $9,000 club capital contribution and up to $1,000 in working capital are theirs to pay. And we tell sellers what the last twelve months say plainly: every Chatham Square II sale closed below list, the median sale took almost seven months, and the listings that sell are priced to the current asks and documented on the milestone question before the first showing.
We walk every Chatham Square II showing with the building file in hand. Selling a Chatham Square II condo? Get a free Chatham Square II home valuation or call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
If you’re searching for a Chatham Square II listing agent, or thinking, ‘I need someone to sell my Chatham Square II home…’, McGreevy and Comisar are the team to call. We price a Chatham Square II condo by building, plan and floor, document the milestone record before the first showing, and market it to the seasonal and out-of-state buyers who own most of Chatham Square II today.
Why sellers list with McGreevy and Comisar:
Recent Chatham Square II sold-listing statistics: In the last 12 months Chatham Square II has seen 4 resales in the Southwest Florida MLS, for $1,000,500 in total volume, at a median 209.5 days on market and an average 90.8% of list price; the sales were $210,000, $257,500, $265,000 and $268,000. Over five years, 13 closings, a $295,000 median, 83 median days on market and 96.1% of list. The MLS pull did not record the listing office on each sale, so we do not state how many we represented on the seller side; in the last 12 months we tracked every Chatham Square II closing, listing and recorded deed by building and plan for this guide.
Selling a Chatham Square II condo is selling a building as much as a unit. Five things decide the result:
Your Chatham Square II condo’s value starts with its plan and building (the 1,275-square-foot end units sold at $268,000 and $350,000 in the last two years, the 1,097-square-foot interiors at $257,500 to $319,000) and adjusts for floor, view, updates and the building’s milestone stage. Get a free Chatham Square II home valuation and we will price it against the actual Chatham Square II sales and current listings.
Talk to Jesse direct: (239) 898-6072, text or call. Confidential conversations welcome.
The median Chatham Square II sale in the last twelve months took 209.5 days on market in the Southwest Florida MLS; over five years the median was 83 days. A condo priced near the two current asks ($215,000 and $225,000) and listed with the milestone file ready competes on the right terms; one priced to 2024 prices waits.
It can if it is a surprise. Buildings E, F, H and I show as delinquent on the county roster with Phase 2 repairs permitted; Building G is completed. Have the county record, the engineer’s summary and the association’s repair plan and budget in hand before listing, and price for the buyer’s view of the remaining work.
Yes. Section 14 of the restated Declaration requires the board’s written approval before closing, with at least 20 days’ notice and a copy of the signed contract. The board may interview the buyer and must act within 20 days of receiving everything.
The buyer. The club’s Resale Capital Contribution ($9,000 for a golf unit in 2026) is owed by the purchaser under the club declaration, and the association’s working capital contribution (up to $1,000) is owed by the purchaser under section 14.7. Both still affect your price, because a buyer adds them to the cost.
You can, but the leasing rule narrows the pool: leases of one to three months, no more than three a year. An investor who wants seasonal rentals fits; one who wants an annual tenant does not.
Late fall through early spring, when seasonal buyers are in Naples and the club’s open-house weekends draw traffic. A summer listing faces fewer buyers but also fewer competing Chatham Square listings.
Chatham Square II owners and buyers work directly with Jesse McGreevy and Marc Comisar, Top 1% Real Estate Agents Nationally Since 2008, not with a call center. Between them they bring more than twenty years of Southwest Florida transactions, and they read the Chatham Square II declaration, the county’s milestone records and every recent Chatham Square sale before writing this guide.
McGreevy and Comisar are the Domain Realty team behind this guide: Jesse McGreevy, Sales Associate, and Marc Comisar, Broker Associate. Jesse has been in the business since October 2004 and the team launched in October 2008. Read how the team was built on our about the McGreevy and Comisar team page.
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate. The credentials:
McGreevy and Comisar is a top-reviewed Chatham Square II realtor on Google, and the quotes below are genuine five-star client reviews in the reviewers’ own words. We publish no aggregate score. Read the full set on the McGreevy and Comisar Google Business Profile.
★★★★★ “Marc Comisar did an excellent job working with a very difficult client (me) selling our condo in a tough condo market. He went above and beyond.” Verified Google review
★★★★★ “Their recommendation on pricing my unit was sound and proved prescient. I never questioned their integrity and found it easy to rely on their recommendations. I would work with them again in a heartbeat.” Verified Google review
★★★★★ “Jesse was very professional, helpful and kept in touch with ideas and suggestions which developed into a sale. Highly recommend his company for their excellent follow through.” Verified Google review
★★★★★ “So knowledgeable! You can tell they truly have a high level of expertise and were incredibly professional from start to finish.” Verified Google review
★★★★★ “Marc knows the market, works for his buyer and is attentive to his goals.” Verified Google review
Selling a Chatham Square II home? Get a free Chatham Square II home valuation, or call Jesse direct at (239) 898-6072.
Buying at Chatham Square II? Call Marc at (239) 287-5873, or read how we represent buyers in Naples.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
Video walkthroughs and market updates are on McGreevy and Comisar on YouTube, and the team keeps a company page at McGreevy and Comisar on LinkedIn. For the community around Chatham Square II, see our Glen Eagle guide and our Naples guide.
Chatham Square II is the five three-floor buildings on the north arc of Dennis Circle, at 7105, 7065, 7025, 6985 and 6945 Dennis Circle, inside Glen Eagle Golf & Country Club off Davis Boulevard in East Naples, ZIP 34104.
120: five buildings of 24 homes each, per the Collier County tax roll and the Florida condominium records.
No. They are separate condominiums with separate associations and declarations. Chatham Square I is the 96 homes in eight two-floor buildings on the rest of Dennis Circle. They share the Chatham Square Commons pool, tennis court and roads, a manager and one MLS name.
Three residential floors of eight homes, numbered 101 to 308 on the county roll. The club’s packet groups Chatham Square II with Glen Eagle’s “3 or 4-story” buildings.
The restated Declaration lists a common utility and elevator room among the elements the association maintains. Confirm the elevator for the specific building, and its service record, with the association’s manager.
Three on the county roll: 1,097 square feet (70 homes), 1,209 square feet (20 homes, the 04 and 05 positions on the second and third floors) and 1,275 square feet (30 end homes).
Units ending in 01 and 08 on every floor of every building: 101, 108, 201, 208, 301 and 308. They are the 1,275-square-foot plan.
The four MLS closings of the last twelve months were $210,000 to $268,000, and the two listings on September 26, 2026 asked $215,000 and $225,000. The five-year MLS median is $295,000.
The median of the last five years was $268.92 per square foot of MLS living area; the four sales of the last twelve months had a median of $222.46.
Yes, from their 2022 peak. The 2022 closings reached $385,000; the 2026 closings to date sit between $210,000 and $268,000, and the county’s qualified-sale median fell from $300,000 in 2021 and 2022 to $266,500 in the year to August 2026.
A median 209.5 days on market in the last twelve months, and 83 days over five years, in the Southwest Florida MLS.
The condominium’s own assessment is not published; ask the manager for the current budget. On top of it, a golf unit pays $8,031 a year in 2026 club dues and a $600 food and beverage minimum.
Yes for 119 of the 120 units, which carry a golf membership under the club’s recorded designation exhibit; one unit carries a social membership. Confirm the designation for the specific unit before you write an offer.
For a golf unit, the club’s $9,000 Resale Capital Contribution ($4,500 if you already own in Glen Eagle), the club transfer and estoppel fees as the contract assigns them, and the association’s working capital contribution of up to $1,000.
No. Glen Eagle has no community development district, per the county’s CDD boundary layer and the state’s official list of special districts.
No. It is an all-ages condominium; the Declaration requires only that residents under 18 be supervised by an adult.
Only seasonally: one to three months per lease, at most three leases a year, each approved by the board, and no more than three months a year to the same tenant.
No. The restated Declaration caps any lease at three months.
No. Section 12.6(F) of the restated Declaration bars pets for tenants and guests.
One dog or one cat weighing 30 pounds or less at maturity, plus up to two birds and tropical fish.
Yes, with the board’s written approval, a licensed contractor and an underlayment meeting a sound transmission class rating of 68, under the 2015 amendment. Bedrooms are no longer carpet-only.
Yes, if they match the standard model, style and color the board has adopted; the board may not refuse a conforming shutter.
One assigned covered carport space as a limited common element under section 8 of the restated Declaration. Owners may swap spaces by written agreement with board approval.
Building G (7025 Dennis Circle), completed with its next inspection due in 2035, per Collier County’s roster on September 26, 2026.
Buildings E, F, H and I, with Phase 2 concrete repairs permitted and recorded on September 26, 2025.
We could not confirm it from public records: the state’s database of SIRS submitted in July 2025 or later did not list Chatham Square II on September 26, 2026. Ask the association for the study and its funding plan.
We found no public record of one. Milestone repairs and SIRS reserves are the costs to ask about; the association’s estoppel certificate must disclose any assessment due.
Zone X at all five buildings on the effective 2024 FEMA map and on the preliminary map, with Building I in the 0.2% annual chance (shaded X) area.
Most lenders do not require it in Zone X, but a narrow Zone AE strip runs along the lake edge near Building F, and Citizens policyholders face a flood-coverage requirement. Price an HO-6 flood endorsement either way.
Zone C on Collier County’s evacuation map.
Calusa Park Elementary (A), East Naples Middle (A) and Lely High (B), per the district’s address lookup for 2026-27 and its 2026 grades.
Yes. The main entrance on Davis Boulevard has a staffed gatehouse.
Anchor Associates, Inc., 2340 Stanford Court, Naples, per the Florida condominium records and the club’s 2026 packet; phone 239-649-6357.
Yes. The seller gives at least 20 days’ notice; the board may interview you and must act within 20 days of receiving everything it asked for.
The restated Declaration allows ownership by a trust or entity with the board’s approval, conditioned on naming one natural person as the primary occupant.
Any unit empty for a month or longer needs a condo watcher inspecting it at least monthly, and the association must have a current key.
Chatham Square II is cheaper and offers three plans and third-floor views, with open milestone work and seasonal-only leasing; Chatham Square I has garages, a single 1,308-square-foot plan, no milestone obligation and leases up to a year. The comparison table above sets them side by side.
Not reliably. Third-floor units sold at both the top ($385,000 in 2022) and near the bottom ($265,000 in 2026) of the five-year range; plan, timing and condition moved prices more than floor did.
For a buyer who wants a Glen Eagle golf membership near the lowest price and understands the milestone and reserve obligations, it offers value; for a buyer who wants annual rental income, the leasing rule rules it out.
Call Marc at (239) 287-5873. We pull the building’s milestone file, the recorded repairs, both flood maps and the association’s approval requirements before you write an offer.
Start with the last twelve months of Chatham Square II closings ($210,000 to $268,000) and the two current asks ($215,000 and $225,000), then adjust for plan, floor, view, updates and your building’s milestone stage. Get a free Chatham Square II home valuation and we will price it against every recent sale.
Four in the Southwest Florida MLS from September 26, 2025 to September 26, 2026, plus one more recorded deed ($284,000 in April 2026) that did not go through the MLS.
Because buyers are pricing the milestone repairs, the reserve law and a slow market: all four sales of the last twelve months closed below list, at an average 90.8%. Sellers who price to the current asks and document the building close closer to their price.
The median of the last twelve months was 209.5 days on market; the five-year median was 83 days. Pricing and documentation are the two levers you control.
If you plan to sell within a year, list for the November-to-April season with the milestone file ready. Prices have fallen from the 2022 peak, so the question is less timing than positioning against the two current listings.
Yes. Building G has completed its milestone inspection (next due 2035); Buildings E, F, H and I show as delinquent with Phase 2 repairs permitted. A buyer will ask which building, and a completed building is easier to finance and insure.
Yes. The 1,275-square-foot end units have sold at $268,000 and $350,000 in the last two years, the 1,209-square-foot units from $210,000 to $385,000 over five years, and the 1,097-square-foot interiors from $257,500 to $319,000.
Less than plan and building. Third-floor units have sold at both the top and near the bottom of the five-year range.
Update what a buyer’s inspector and insurer will flag first: the water heater, shut-off valves, supply lines and condensate line on the Declaration’s High-Risk Components schedule, and the age of the air conditioning. Cosmetic updates come second.
Many Chatham Square II buyers are seasonal, so furnished can widen the pool. Price the furnishings separately in the contract so the appraisal sees the real estate price.
Florida’s resale disclosure law, section 718.503, requires the buyer to receive the inspector-prepared summaries of any milestone inspection and structural integrity reserve study. Disclose your building’s status and the repairs; buyers find it on the county map anyway.
Disclose the stage, give the buyer the engineer’s summary and the association’s plan, and settle in the contract who pays any assessment adopted before closing. A clear allocation keeps the deal together.
The contract decides, and the standard Florida condominium contract forms address it expressly, so settle it before you sign. The association’s estoppel certificate will show what is due.
The contract assigns them. A Chatham Square II sale needs the association’s estoppel and the club’s ($299, or $399 if needed in under five business days).
Yes. Give at least 20 days’ notice before closing with the signed contract; the board may interview the buyer and must act within 20 days of receiving everything.
Only for the listed good-cause reasons in section 14 of the restated Declaration. If it disapproves without good cause and you made a written demand, it must supply an approved buyer at the same price and terms.
The buyer, at closing, under Article 11.12(B) of the club declaration. A buyer who already owns in Glen Eagle pays $4,500.
The buyer, up to $1,000, under section 14.7 of the restated Declaration as amended in 2015.
No. The restated Declaration bars sale, rent and open-house signs on the condominium property, including windows and lanais. The club’s procedure places open-house signs at the entrance and lets your agent mark the open unit at the building.
The club posts open-house signs at the entrance on Saturday and Sunday from noon to 4 p.m.; your agent registers the open house with the club, uses only the standard signs, and at Chatham Square II may mark the open unit number at the building.
Yes, but only an investor who accepts seasonal leasing: one to three months per lease, at most three leases a year.
Yes, if the lease was approved; the lease cannot exceed three months, so time the closing to its end or assign the remaining weeks to the buyer in the contract.
You can, but a Chatham Square II sale runs on documents most owners do not keep: the milestone record, both estoppels, the association approval, the capital contributions and both flood maps. Pricing and documentation are where an agent earns the fee.
Start from the price, then subtract the commission, Florida documentary stamp tax on the deed, title and closing charges, the estoppel fees your contract assigns to you, prorated condominium and club dues, and any assessment you owe. The buyer pays the club capital contribution and the working capital contribution.
Yes. The membership is attached to the unit under the club’s recorded designation exhibit and passes with the deed; the buyer pays the club’s transfer fee and capital contribution.
Yes. All five buildings are in Zone X on both the effective and preliminary FEMA maps; show the buyer the building’s zone so a lender does not assume otherwise. If your building is F, be ready for a question about the lake-edge strip.
Florida’s flood disclosure law, section 689.302, requires a seller to disclose, among other things, whether the seller has filed a flood insurance claim or received federal flood assistance for the property. Complete the form with your agent before the contract.
The building’s county record (PL number on this page) holds the reports and letters in the Documents and Images tab of Collier County’s GMCD portal, and the repair notices are public at the Collier Clerk. We assemble them for our sellers.
It narrows the buyer pool to owner-occupants, second-home buyers and seasonal investors. Price against Chatham Square II sales, which already reflect the rule, not against Glen Eagle condominiums that allow annual leases.
Chatham Square I’s five-year MLS median is $360,000 across 22 closings, against $295,000 for Chatham Square II; Chatham Square I’s units are larger (1,308 square feet), have garages and are outside the milestone law.
Late October or November, so the listing is ready for the seasonal buyers who arrive from November to April.
We price by building, plan and floor from every Chatham Square II sale, assemble the building file (milestone record, repair permits, flood maps, budget, approval packet) before the first showing, and market to the seasonal and out-of-state buyers who make up most Chatham Square II owners. Call Jesse at (239) 898-6072.
Choose an agent who can tell you, before listing, your building’s milestone status, the recorded repair permits, both flood zones, the association’s approval timeline and the price of your plan over the last five years. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008 and the #1 team in Southwest Florida since 2012, and this guide is our answer.
Only if the numbers work. A three-month winter lease can cover part of the carrying cost, but it complicates showings in the months buyers visit, and while the unit is leased you lose use of the recreation and parking facilities.
Every source below is a primary record: county, state and federal agencies, the recorded documents at the Collier Clerk, the Glen Eagle club, the school district and federal imagery. Market figures come from the Southwest Florida MLS (not linked) and the Collier County tax roll (2026 preliminary files dated August 29, 2026), read directly and cited in plain text. Links were checked on September 26, 2026.
Chatham Square II’s governing documents and building records are public at their official sources. Download them from the authority that holds them:
Document | Date and recording | Official source |
|---|---|---|
Amended and restated Declaration of condominium | OR 4474 PG 3011, July 23, 2009 | |
Original declaration of condominium | OR 1592 PG 1656, February 13, 1991 | |
Leasing amendment (three-month maximum) | OR 4166 PG 2519, January 9, 2007 | |
Flood insurance and LOMA amendment | OR 4808 PG 2209, June 19, 2012 | |
Flooring amendment | OR 5188 PG 1790, August 26, 2015 | |
Working capital contribution amendment | OR 5221 PG 242, December 7, 2015 | |
Chatham Square Commons declaration | OR 1558 PG 1174, September 13, 1990 | |
Commons quiet-title judgment | OR 5324 PG 1240, October 18, 2016 | |
Milestone Phase 2 repair notices, Buildings E, F, H, I | OR 6511 PG 2094 to 2097, September 26, 2025 | |
Club 2026 Realtor’s Packet | 2026 | |
Club master declaration and bylaws, with membership designations | 2015 restatement | |
Collier milestone buildings by year | as of January 2026 |
The association’s budget, reserve schedule, structural integrity reserve study, milestone reports and insurance schedule are held by the manager or filed with the county; owners and buyers under contract request them from Anchor Associates, and the county’s milestone reports are in each building’s record on the GMCD portal.
Market data from Southwest Florida MLS, pulled September 2026.McGreevy and Comisar, Best Realtor for Chatham Square II at Glen Eagle. Brokered by Domain Realty. Jesse McGreevy, FL Lic. SL3101296 · Marc Comisar, FL Lic. BK3060671.
Thinking about buying or selling in Southwest Florida? Tell us what you are trying to do and we will tell you honestly what it will take. McGreevy and Comisar, Domain Realty Group.
