260 CHESHIRE WAY, Naples
Naples Homes for Sale
Naples is a Collier County market built first around its beach, with a verified public beach right here in the area. Golf sits close behind: roughly one in six listings are in golf communities, so a course-side address is a normal option rather than an unusual one. Boating is the third thread, with a verified marina in the area, which matters if a boat is part of the plan. Put together, that gives you three different kinds of purchase under one market name, and the homes for sale range from attached units to whole parcels with water behind them. The Fahey Team works this market daily and knows how those pieces fit.
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- Homes Between $750,000 to $1,000,000
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Naples at a Glance
- County
- Collier County
- Typical asking price
- $682,500, middle half $399,000-$1,399,000 (median of 4,040 homes, excluding 821 land and other non-dwelling listings)
- Typical sold price
- $605,000, middle half $400,000-$1,100,000 (median of 8,845 home sales, excluding 593 land and other non-dwelling sales, past 12 months)
- Typical home
- 1,800 sq ft, middle half 1,360-2,530 (n=4,039) · 3 bed / 2 bath (medians, n=4,007)
- Typical days to sell
- 96 days (median of 8,845 closed home sales, past 12 months)
- Months of supply
- 5.5 (balanced, homes only)
- Sold-to-list
- 95.1% of asking (median per home sale, n=8,844) · 3.9% sold above asking
- Waterfront
- Lake 19% · Canal Front 6.2% · Bay 5% · Gulf Frontage 2.4% · On the Gulf Beach 1.8% (roughly a third have some water frontage)
- Data current as of
- August 2026, M.L.S. of Naples, Inc
Condo or house: what each side of the search feels like
The first real decision in Naples is between a condo and a single family home, and the two shop nothing alike. Single family listings here tend to find their buyer, so when one lines up with what you want, treat it as a decision you make on the spot rather than one you sit on. Condos work the other way: more selection at any given moment, and more time to walk through several before you commit. If you want to compare carefully, the attached side rewards that. If you want the house, be ready with financing and a plan before you tour.
The attached side of Naples
Nothing outside your own front door is yours to organize on this side of the market. You can be gone for months and come back to a building that was looked after while you were away, and that is the real appeal of holding just the interior. The fee is the other half of it, running around $12,096 a year at the median, so read any listing's number against what the association actually carries before you judge it. Median sale price is $415,000, and typical time to sell is about 104 days, useful when you are mapping out a closing and a move. Stock here typically dates from 1995. Building styles lean low rise of one to three floors, more than half of what sells, with high rise of eight or more at roughly one in six and mid rise about one in ten. About half of these communities are gated, roughly a third are not, and about a quarter include tennis. Ask which association documents govern rentals if you ever plan to let the unit out.
Whole parcels in Naples
Buy a single family home here and you own the ground as well as the building, so what happens to the yard and the driveway is between you and the county, with no association standing in the middle. That is a real freedom, and it comes with the roof, the irrigation and the landscaping on your own calendar and your own budget. The median sale sits at $725,000, and homes on this side typically take about 90 days to sell, which is worth knowing when you are timing a move. Where there are fees, the median is about $5,600 a year, so ask what a given community's dues actually cover. Typical construction year is 2010. Almost all of this segment is detached single family, with small shares of attached villas and townhouses. Roughly a third of these communities are gated and roughly a third are not, and about one in six offer tennis. On a detached parcel, ask about impact windows and the age of the electrical panel.
Naples houses with water of their own
A pool of your own turns a swim into a decision instead of an arrangement, and the only schedule it keeps is yours. That changes how a house gets used, morning and evening, all year. It also means a pump, a heater, a cage and a service visit you either book or do yourself. Pool homes carry a median sale of $1,125,000, so plan the budget around the house and the water together rather than treating the pool as an add-on. Typical time to sell is about 93 days. Where fees apply, the median is around $6,352 a year. Construction is typically from 2013. Nearly all of this group is detached single family, with small shares of attached villas and low rise buildings of one to three floors. Roughly a third of these communities are gated, roughly a third are not, and about one in six have tennis. Ask when the pool was last resurfaced and whether the cage screening has been replaced.
Where the boat leaves from the back of the house
On the water-access side of Naples, the boat lives here and leaves from here, so a morning on the water starts at the back of the house rather than at a marina an hour before it. That is the whole point of this stock, and it comes with pilings, a lift and a service schedule that belong to you. Median sale price is $1,200,000, so plan financing around a house and a working waterfront structure together. Recurring fees run a median near $17,300 a year, which you should read as what the association carries rather than as a flat surcharge. These homes typically date from 1987. Roughly a third of what sells here is a single family residence, about a quarter is high rise, and roughly one in six is low rise, so the same access can arrive as a house or as a unit. Most of it sits in boating communities, about half non-gated, about a quarter gated. Naples City Dock is in the area, worth knowing before you rule out a listing without frontage.
Living on the sand in Naples
Beachfront here means the shoreline becomes an ordinary daily thing rather than an outing, with an outlook across open water that no future construction can take away. The median sale in this group is $2,000,000, so come in with financing settled. These buildings typically date from 1981, and more than half of what trades on the sand is high rise, so expect elevators, shared corridors and a building-wide approach to the exterior. Frontage is what you are buying, and it is finite: there are only so many of these lines of units, and the inventory is small. If you are placing yourself on the shore, Park Shore Beach is in Naples as well. Typical time to sell in this group is around 118 days. Ask what a unit's assigned parking and storage actually include before you write.
What owning here asks of an owner
Across Naples as a whole, the typical home dates from 2000, with the middle half falling between 1989 and 2014. At that age a roof, an air handler and a water heater come due, so on any listing you are serious about, ask what has already been replaced and what is still original. Recurring fees across the area run a median of about $8,716 a year, with the middle half between $5,800 and $15,651. Read a fee as what it buys: one near the top of that range is usually covering amenities, insurance and exterior maintenance that a lower one leaves you to arrange and pay for yourself. Establish early whether a property is governed by an association with rules and documents, or sits in no subdivision at all with nothing between you and the county. The most common layout sold is a three-bedroom, at a median of $655,000, which is a fair place to locate yourself. Land and other non-dwelling listings are roughly one in six of what is active, typically around $258,500, and about half of those are in Golden Gate Estates.
What buyers filter for here
Views split the field more than people expect. About half of homes have no notable view at all. Of the rest, lake is the most common at about a quarter, trees or woods roughly one in six, general water about one in ten, with smaller shares looking at a canal or the bay. What a home looks at and what it sits on are different filters, so use both. Roughly a third of homes have some water frontage: lake frontage is roughly one in six, with smaller shares on a canal, the bay, the Gulf, or directly on the Gulf beach. About a quarter of homes have a pool, and that group sells at a median of $1,125,000, so filter on it early if it is non-negotiable. Most listings are resale, with small shares new or under construction; new construction sells at a median of $690,000. About half of listings are unfurnished, with turnkey and negotiable each roughly one in six, and pet terms vary between yes, limits and approval.
Which parts of Naples the listings come from
Only one community here is large enough in the listing count to be worth naming: Golden Gate Estates, at roughly one in six of active listings. Everything else sits in smaller communities with no name a buyer would think to type into a search box. That matters practically. A name-based search misses most of this market, so build your search on the filters that actually sort it: water frontage, property class, and price band. Start there, then let the community names show up as results rather than as your starting point. If you already have a name in mind, use it as one lane and keep a second, broader search running alongside it.
Worth confirming before you write an offer
- Dock and boat lift capacity for canal or bay access.
- Septic versus sewer service for the lot.
- Find out the seawall's age and condition and who is responsible for repairing it.
- If you plan to keep a boat, measure the clearance and the depth on the run to open water before you commit.
- Ask how the association's insurance is placed and whether its compliance status affects coverage or financing on the unit.
Working with the Fahey Team
The Fahey Team works Naples closely enough to know how a listing actually differs from the one two streets over, and to tell you plainly what a given property will ask of you once you own it. That is most of the value: someone alongside you who has seen enough of these to know which questions to put in writing before you sign anything. What is left is your call. Condo or single family home is the first fork, and a pool home is the other kind of purchase buyers here weigh. Decide which of those matches how you actually plan to live, and the rest of the search gets much simpler.
Newest Homes for Sale in Naples, FL
The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.