Mindy DolleDomain Realty · Naples
(239) 851-2556
Naples, FL · Street guide

Homes for sale on Cheshire Way

As of November 3, 2026, 2 homes listed at $3M and up are for sale in Cheshire Way, Naples, FL, priced from $3.19M to $4M with a median asking price of $3.6M (about $976 per square foot).

2Active homes $3M+
$3.19M – $4MList price range
$976Median list $ / sq ft
3Closed sales, 12 months

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Homes on Cheshire Way

2 at $3M+
260 Cheshire Way, Naples1 / 50
$3,995,000
260 Cheshire WayAudubon Country Club · Naples
3 bd3.5 ba3,272 sf
Listing courtesy of Keller Williams Elite Realty
168 Cheshire Way, NaplesNew today1 / 49
$3,195,000
168 Cheshire WayAudubon Country Club · Naples
3 bd4.5 ba4,366 sf
Listing courtesy of John R Wood Properties
188 Cheshire Way, NaplesNew · 3 days1 / 47
$2,950,000
188 Cheshire WayAudubon Country Club · Naples
3 bd3.5 ba3,959 sf
Listing courtesy of John R Wood Properties
268 Cheshire Way, NaplesNew · 6 days1 / 45
$2,895,000
268 Cheshire WayAudubon Country Club · Naples
4 bd4.5 ba3,979 sf
Listing courtesy of Florida Prime Realty, LLC
196 Cheshire Way, NaplesWaterfront1 / 45
$2,850,000
196 Cheshire WayAudubon Country Club · Naples
4 bd3.5 ba3,885 sf
Listing courtesy of John R Wood Properties

Listings are shown courtesy of the listing brokerages. Information is deemed reliable but not guaranteed.

Questions about Cheshire Way

How many homes over $3M are for sale in Cheshire Way?

2 homes priced at $3M or more are listed for sale in Cheshire Way, Naples, FL, according to the MLS as of November 3, 2026, out of 5 active listings overall. The list changes daily.

What do luxury homes cost in Cheshire Way?

Current asking prices at $3M and up run $3.19M to $4M, with a median of $3.6M or roughly $976 per square foot. Floor, view, finish and, for single-family homes, lot and water frontage account for most of the spread.

What kinds of homes are in Cheshire Way?

Cheshire Way is a street in Naples in Naples, FL. Current listings include homes with 3 bedrooms, 3,272 sq ft to 4,366 sq ft, built 1998 to 2001.

Are homes in Cheshire Way on the water?

Of the 2 current listings, 1 is waterfront, 2 have a private pool, per MLS data. Water type and access vary by street and building, so confirm each home's details before relying on them.

How fast do homes sell in Cheshire Way?

3 sales closed in the past 12 months at a median of $2.55M, with a median of about 38 days on market and a median sale-to-list ratio of 88.7%. A small number of sales means these medians are only a guide.

What should I check before buying a home in Cheshire Way?

Start with the association: the budget, reserves and any special assessments. Then check the flood zone and elevation, an insurance quote, any club or amenity membership and its transfer rules, and what comparable homes have actually sold for. Mindy can pull the closed sales for Cheshire Way and walk you through the documents.

Which communities are on Cheshire Way?

Current listings on Cheshire Way sit in Audubon Country Club (5). Each community has its own association rules, fees and amenities, so compare them before you choose.

Who can show me homes in Cheshire Way?

Mindy Dolle, a licensed Florida real estate sales associate with Domain Realty, can arrange showings, pull comparable sales and review association documents for homes in Cheshire Way. Call or text (239) 851-2556.

Along and near Cheshire Way