Chatham Square
What has actually sold in Chatham Square over the last twelve months, and what is on the market there today.
across 10 sales in a year
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on the market today
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for the typical home
what sellers actually got
on the typical sale
of homes that sold
What kind of place it is
Association dues here run about $1,088 a month. That is what the listings say they are paying, not a quote, and it is the number people forget when they work out what they can afford.
Middle and high school here run on school choice rather than a fixed zone, and each high school has its own focus. Fort Myers is advanced academics, South Fort Myers is career and technical, Cypress Lake runs the Center for the Arts, Dunbar leans to cybersecurity and networking. Which one suits depends on the child, not the address, so it is worth a conversation with the district before you assume anything.
Read off the 6 homes for sale here, and listed only where most of those listings agree. Anything one or two agents claimed on their own is left out, which means this is shorter than the brochure and likelier to be true. Associations change their rules, so confirm anything that would change your mind.
What the association gives you
What it takes to buy here
The middle half of sales landed between $257,500 and $342,000. Half of everything sold went under contract inside 87 days.
40% of sales here were on the water, which is the thing that sets the price in this part of Naples more than square footage does.
Listings open in our search. The MLS requires an account before it will show you listing detail and sold prices, which takes a minute.
Before you offer on anything here
Your taxes reassess when you buy, so the seller's bill is not yours. Insurance depends on the roof and the flood zone. Both matter more than the price you negotiate.
Questions people ask about Chatham Square
Is Chatham Square gated?
No. Chatham Square is an open neighbourhood with no gate on the entrance.
Is Chatham Square a 55 and over community?
No. Chatham Square is open to all ages.
What are the HOA fees in Chatham Square?
Association dues run about $1,088 a month, adding up every fee the listings disclose. Ask for the current budget and any assessment on the table before you offer, because dues are the part of the payment that moves after closing.
Does Chatham Square have golf?
Yes. Listings in Chatham Square carry a golf course. Whether membership is included, optional or mandatory varies by community and it is worth asking early, since a mandatory membership can add a large one-off fee at closing.
How much do homes in Chatham Square sell for?
The median sale in Chatham Square over the last twelve months was $274,000, across 10 closings. The middle half landed between $257,500 and $342,000. There are 3 homes for sale there today.
How long does it take to sell in Chatham Square?
Half of what sold went under contract within 87 days. Sellers got 95.2% of what they asked. A home sitting far longer than that is usually telling you something about its price rather than about the neighbourhood.
Also in Naples
Golden Gate Estates
717 sales · 453 for sale
Naples Park
138 sales · 96 for sale
Isles Of Collier Preserve
128 sales · 49 for sale
Golden Gate City
118 sales · 37 for sale
Island Walk
111 sales · 27 for sale
Verona Walk
95 sales · 36 for sale
Thinking about Chatham Square?
Numbers will not tell you which streets flood or which association is about to assess. Ring and ask.
Aggregated from Florida Gulf Coast Multiple Listing Service data, twelve months of closed sales filtered to homes. Information is deemed reliable but is not guaranteed accurate by the MLS. A median is not a valuation of any particular property. Rebuilt 2026-08-26.