253 Cheshire WAY Naples, FL $ 3,999,000
253 Cheshire WAY
$ 3,999,000
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253 Cheshire WAY

Naples, FL, 34110
$ 3,999,000
Bedrooms4 Baths4.2 Sq 6,026

Monthly Estimate*

$ 24,623

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Single Family Home for sale in Naples, FL

for $3,999,000 with 4 bedrooms and 4 full baths, 2 half baths. This 6,026 square foot home was built in 2002 on a lot size of 0.41.

Your Naples Sanctuary Awaits – Completely Reimagined for 2026 Imagine your perfect Naples winter: morning coffee overlooking championship fairways, afternoons by your resort pool, sunset cocktails as Gulf Coast skies ignite in color. This meticulously transformed Audubon estate delivers it all. No Expense Spared Every surface, every finish thoughtfully updated to today's most discerning standards. Fresh paving, new exterior and interior paint, soaring ceilings, gleaming marble floors, and custom finishes throughout. Expansive pocketing doors erase boundaries between indoor and outdoor living, framing spectacular southern golf course views. Chef's Kitchen & Living Spaces The show-stopping kitchen features custom cabinetry, professional appliances, and dual oversized islands—the natural gathering spot. Floor-to-ceiling windows bathe living and dining areas in natural light while showcasing panoramic views. Owners exclusive retreat area designed for indoor/outdoor meditation & yoga. Master Suite Sanctuary Your private retreat offers a sitting area perfect for morning reflection or remote work. The completely reimagined spa bathroom showcases modern finishes, while his-and-hers facilities ensure personal luxury. Resort-Style Outdoor Living Newly renovated pool with sun shelf and spa. Designer gazebo with full outdoor kitchen and bar. Spectacular golf course backdrop. Lush landscaping ensures privacy while showcasing sweeping views. Every sunset becomes an event. Guest Wing Excellence Dedicated upstairs wing with two elegant suites, private baths, living room with kitchenette, and balcony offering panoramic Gulf Coast views. Audubon Country Club Private, gated community featuring championship 18-hole golf, tennis, pickleball, fitness center, heated lap pool, courtside café, vibrant social events, scenic nature trails, and kayak launch. The Opportunity 4 bedrooms | 6 bathrooms | Southern golf course views | Completely updated | Fresh to market January 2026 After extensive renovations, this estate represents exceptional value in Naples' most desirable private golf community. Your winter escape awaits.

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Single Family Pending

Price

$ 3,999,000

Bedrooms

4

Full Bath

4

Half Bath

2

Property Type

Single Family

Taxes

$ 22,833

Style

Two Story,Single Family

Lot Size

0.41

Year Built

2002

Town/City

Naples

County/Region

Collier

MLS | Web ID

225084896

Features
Interior
Interior Amenities Fireplace Foyer Laundry Tub Volume Ceiling Walk-In Closet(s) Window Coverings Zero/Corner Door Sliders
Flooring Marble Wood
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N Y
Heating Y/N Y
Window Features Window Coverings
Fireplace Y/N Y
Half Baths 2
Laundry Features Laundry in Residence Laundry Tub
Total Bedrooms 4
Total Baths 6
Dining Room Features Eat-in Kitchen Formal
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General
Heating Central Electric
Cooling Ceiling Fan(s) Central Electric
Roof Tile
Appliances Gas Cooktop Dishwasher Disposal Double Oven Dryer Freezer Grill - Gas Microwave Range Refrigerator/Icemaker Reverse Osmosis Washer Wine Cooler
HOA Fee 17030
Garage Spaces 3
Gas Y/N Propane
Patio/Porch Features Patio
Architectural Style Two Story Single Family
Pool Features Community Pool/Spa Combo Below Ground Custom Upgrades Gas Heat
Security Features Security System Smoke Detector(s) Gated Community
Construction Materials Concrete Block Wood Frame Stucco
Pets Allowed Yes
Year Built 2002
View Golf Course
Levels 2
Property Subtype Single Family Residence
Tax Year 2024
Waterfront Features None
Community Features Clubhouse Park Pool Fitness Center Fishing Golf Putting Green Restaurant Sidewalks Street Lights Tennis Court(s) Gated
County Collier
New Construction N
Property Type Residential
Association Amenities Bocce Court Cabana Clubhouse Park Pool Community Room Fitness Center Fishing Pier Golf Course Internet Access Library Pickleball Putting Green Restaurant Sidewalk Streetlight Tennis Court(s) Undergro
HOA N
Attached Garage Y
Subdivision Name AUDUBON COUNTRY CLUB
Garage Y/N Y
Other Structures Cabana Tennis Court(s) Gazebo Outdoor Kitchen
Total Rooms 0
Full Baths 4
Status Pending
High School AUBREY ROGERS
City NAPLES
Senior Community Y/N N
Number Of Units Total 1
MLS Area AUDUBON
Lot Size Units Acres
Lot Size Square Feet 17860
Carport Spaces 0
Carport Y/N N
Spa Features Below Ground Heated Gas Pool Integrated Screened
Elementary School NAPLES PARK
Land Lease Y/N N
Tax Annual Amount 22833.04
Middle/Junior High School NORTH NAPLES
Ok to Lease Buyer Finance/Cash
Additional Parcels Y/N N
Virtual Tour https://www.zillow.com/view-imx/93788909-fe01-4716-be81-0cc18ebc2cee?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard https://lacasatour.com/property/253-cheshire-way-naples-fl-34110/ub
Structure Type House
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
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Exterior
Exterior Amenities Balcony Screened Lanai/Porch Built In Grill Outdoor Kitchen
Parking Features Circular Driveway Attached
Lot Features Golf Course Oversize
Water Source Central
Total Parking 3
Lot Size Area 0.41
Foundation Details Concrete Block
Park Name AUDUBON
Spa Y
Building Area Total 8271
Lot Size Acres 0.41
Frontage Type Golf Course
Waterfront Y/N N
Covered Spaces 3
Door Features Zero/Corner Door Sliders
Other Equipment Generator
Horse Y/N N
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Internal Only
Street Number 1 253
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* Excluded Features
List By
Downing Frye Realty Inc.

Broker

Affordability Calculator

$26,525
Per Month
93%
7%
0%
Monthly Principal & Interest
$24,623
Monthly Property Taxes
$1,903
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4158624 Elementary School
4102080 Middle School
Aubrey Rogers High School High School
Pricing History
DatePricePrice ChangeDescription
2/26/2026$3,999,000 -11.03% Price Down
1/3/2026$4,495,000 Listed Price

Map


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253 Cheshire WAY, Naples, FL, 34110 is a Single Family Home for sale at $3,999,000 with 6,026 sqft and a lot size of 0.41. 253 Cheshire WAY has 4 bedrooms, 4.2 baths, and was built in 2002. The property's zip code is 34110 which is in Naples, FL