Chatham Square
Condos for Sale in Naples, FL
All 2,052 homes for sale in Naples, FL · median $429,000 · 1,840 condos for sale in Naples · 224 homes for sale in 34104 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Florida Gulf Coast MLS
As of October 2026, Chatham Square in Naples, FL has 6 homes for sale and 1 pending, asking from $215,000 to $424,900 (median $274,000). Over the 12 months ending 2026-09-20, 10 recorded sales closed at a median of $266,500, $231 per square foot, a median 87 days on market, sellers accepting 88% of original asking (-24% versus the prior year). Homes listed or recently sold were built 1991–1992; 7 of 7 report an HOA (median $669/mo); none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 11 ft). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $2,950 ($2,510 with the full homestead exemption).
Last 30 days in Chatham Square: 4 new listings (median asking $314,000), 1 under contract right now. As of October 19, 2026, Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate.
Homes For Sale Right Now in Chatham Square
Live MLS inventory for Chatham Square. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Chatham Square listings as of 2026-10-19, priced high to low. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Chatham Square is pricing at a median of $274,000, with a median price per square foot of $235.87 and a typical marketing period of just over 87 days. That combination — a moderate price point stretched over a long selling window — tells you this is not a market where sellers are setting the pace right now. The 21.6% year-over-year decline in median price is the number that matters most here; it reflects either softer buyer demand, a shift in the mix of homes that closed, or both, and a buyer working this community should not assume last year's pricing as a reference point.
With only 10 closings in the current window, the data set is thin enough that a single unusual sale can move the median meaningfully. That is not a criticism of the community, it is a caution about reading too much precision into any one number. The practical takeaway: price here is negotiable and condition-driven, days on market run long enough that sellers need realistic expectations, and buyers have room to negotiate on both price and terms if they are patient.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Chatham Square right now
🔴 Off the recent peak. The trailing-12-month median ($266K) is down 23.8% from the prior 12 months ($350K). With about a dozen sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Florida Gulf Coast MLS closed sales, 12-month windows ending September 20. Confidence: Medium (10 and 6 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 20, 2026 · Live data: Florida Gulf Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Chatham Square market snapshot (as of September 20, 2026): the median sale price is about $266K ($231 per sq ft over the trailing 12 months of closed sales), and a median 88 days on market for closed sales. The trailing-12-month median is down 24% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (10 closings in the current window).
In ZIP 34104 (Naples), 1,347 homes closed in the last 12 months at a median of $570K ($327/sq ft), down 2.4% year over year, with a median 59 days on market. Right now 580 active and 154 pending listings — a buyer's market. See the live ZIP 34104 housing market and the Collier County market.
Florida Gulf Coast MLS sales records identify 12 homes in Chatham Square that have changed hands since 2021, built between 1990 and 1995 (median 1991), with a median living area of about 1,308 sq ft and a typical 2-bedroom, 2-bath layout; 100% are condominiums. Source: Florida Gulf Coast MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Chatham Square is a Naples community currently showing a lower price point relative to broader Collier County activity, with pricing and timing data reflecting a market that favors buyers willing to be patient.
The setting & the homes.
Aerial and on-site photos of Chatham Square. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Chatham SquarePhotos from Florida Gulf Coast MLS listings in Chatham Square; content deemed reliable but not guaranteed.
Who Chatham Square is best for.
Best for
- Buyers targeting a median price point near $274,000 who want negotiating leverage in a slower market
- Buyers with flexible timelines who can tolerate a marketing period stretching toward three months if they later resell
- Value-focused buyers comfortable evaluating homes on individual merit rather than a shared amenity package
Probably not for
- Buyers expecting community amenities such as pools, clubhouses, or organized recreational facilities
- Sellers who need a quick sale and cannot accommodate an extended days-on-market timeline
- Buyers using recent year-over-year price trends as a guarantee of near-term stability or appreciation
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Florida Gulf Coast MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($266K) IS the median in the snapshot above, and the move from 2025 ($350K) IS the -23.8% one-year change.
Windows contain 0 to 17 sales each (10 in the current window); every figure carries its sample size, and thin markets swing on single closings. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
14% of homes for sale in ZIP 34104 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-19).
Chatham Square Market Scorecard
Chatham Square is currently a balanced market., a median asking price of $225,000, and homes go under contract in about 10 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Florida Gulf Coast MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Chatham Square on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Florida Gulf Coast MLS. Map data © OpenStreetMap contributors.
The Chatham Square buying strategy.
If we were buying in Chatham Square today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Chatham Square.
A market that rewards patience, not urgency
The market heat score of 15 is the clearest single signal in this data set — it places Chatham Square well toward the cooler end of the spectrum, and it lines up with everything else: a negative year-over-year price trend, an extended median days-on-market figure near three months, and a limited number of recent closings. None of these numbers individually is alarming, but together they describe a community where sellers are not commanding quick sales or premium pricing right now.
No community amenities were identified from current MLS listings, which means whatever value proposition Chatham Square carries is tied to the homes themselves and their location within Naples, rather than to shared recreational features, clubhouses, or association-run facilities. Buyers should treat this as a straightforward housing purchase — evaluate the individual property, its condition, and its price per square foot against the $235.87 median, rather than weighing in a lifestyle amenity package that isn't part of the current inventory.
The location and the amenities are priced into every listing in Chatham Square. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin, slower-moving data set like this one, pricing a home correctly the first time matters more than it does in a hot market — overpricing here risks adding to an already long days-on-market figure, while underpricing leaves money on the table in a market with only 10 recent closings to benchmark against. We track this community's numbers closely enough to help sellers price defensibly and help buyers know when a listing is priced to the current trend versus priced to last year's market.
Chatham Square in 15 seconds.
Tools for a Chatham Square buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Chatham Square sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chatham Square, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chatham Square home worth?
Get a no-obligation home value based on real comparable sales in Chatham Square, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Recently off market in Chatham Square
Homes in Chatham Square that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 6700 Dennis Cir A102 · off market
| Location | Naples, Collier County, FL · ZIP 34104 |
|---|---|
| Home types (current listings and sales) | condos 100% |
| Sale prices, last 12 months | $266,500 median across 10 closed sales · $231 per sq ft · -23.8% vs the prior 12 months |
| Days on market (closed sales) | 87 median |
| For sale right now | 3 active, 0 pending · median asking $225,000 |
Data as of September 20, 2026. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Market figures describe homes, not residents. Cite as: Momentum Realty, “Chatham Square key facts,” movewithmomentum.com/neighborhoods/chatham-square, data as of September 20, 2026.
Housing distress & ownership in Chatham Square, Naples
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
Just listed in Chatham Square
The newest homes for sale in Chatham Square right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 6945 Dennis Cir 203 $249,000 · 2 bd · 2 ba · 1,097 sq ft · new today Courtesy of Premiere Plus Realty Company
- 6985 Dennis Cir 204 $424,900 · 2 bd · 2 ba · 1,400 sq ft · 3 days on market Courtesy of Coldwell Banker Realty
- 6945 Dennis Cir 205 $299,000 · 2 bd · 2 ba · 1,209 sq ft · 8 days on market Courtesy of Gulf Coast International Prop
- 6740 Dennis Cir 103 $329,000 · 2 bd · 2 ba · 1,308 sq ft · 10 days on market Courtesy of Premiere Plus Realty Company
- 7025 Dennis Cir G202 $215,000 · 2 bd · 2 ba · 1,097 sq ft · 211 days on market Courtesy of Premier Sotheby's Int'l Realty
- 6945 Dennis Cir I-107 $225,000 · 2 bd · 2 ba · 1,097 sq ft · 254 days on market Courtesy of Premiere Plus Realty Company
Checked against the MLS Oct 19, 2026. All new listings in this market.
Every Home for Sale in Chatham Square Right Now (7)
All 7 active and pending Chatham Square listings with a detail page, newest first, refreshed twice a day from the MLS.
- 6985 Dennis Cir 204 · $424,900 · 2 bd / 2 ba · listed Oct 17, 2026 · listed by Coldwell Banker Realty
- 6945 Dennis Cir 205 · $299,000 · 2 bd / 2 ba · listed Oct 11, 2026 · listed by Gulf Coast International Prop
- 6740 Dennis Cir 103 · $329,000 · 2 bd / 2 ba · listed Oct 9, 2026 · listed by Premiere Plus Realty Company
- 6945 Dennis Cir 203 · $249,000 · 2 bd / 2 ba · listed Oct 9, 2026 · listed by Premiere Plus Realty Company
- 6780 Dennis Cir M103 · $365,000 · 2 bd / 2 ba · pending · listed Sep 18, 2026 · listed by Mainstay Brokerage, LLC
- 6945 Dennis Cir I-107 · $225,000 · 2 bd / 2 ba · listed Jul 21, 2026 · listed by Premiere Plus Realty Company
- 7025 Dennis Cir G202 · $215,000 · 2 bd / 2 ba · listed Jul 21, 2026 · listed by Premier Sotheby's Int'l Realty
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What it really costs to own in Chatham Square Condos for Sale
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $2,416/yr across 13 listings here (MLS tax records, 2026-10-20). |
|---|---|
| HOA dues | Median $8,031/year (about $669/month) across 7 MLS listings (most billed annually; 2026-10-20). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Collier County is $2,147/yr (2,002 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 1991 across 13 listings. An original roof here would be about 35 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Estimated carrying cost at the median asking price, before the mortgage: about $1,049/month (tax $201, HOA $669, insurance $179). An estimate from the sources above, not a quote.
Email me new listings in Chatham Square Condos for Sale
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Ask an agent about Chatham Square Condos for Sale
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Frequently Asked Questions
What is the median home price in Chatham Square?
How long do homes in Chatham Square take to sell?
Who is the best real estate agent for Chatham Square?
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Can Momentum Realty connect me with an agent for Chatham Square?
Where is Chatham Square, and what county is it in?
Should you buy in Chatham Square?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: October 19, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2013 (130 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Florida Gulf Coast MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Florida Gulf Coast MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Chatham Square fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Chatham Square Condos for Sale in Naples
- Home values · What homes in Chatham Square Condos for Sale in Naples actually sell for
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