See Home Value
$3,600,000
● House - Off Market

253 Cheshire Way

Naples, FL 34110
bedrooms
4 Beds
bathrooms
4 Baths, 2 Half Baths
square feet
6,026 Ft²
$22,054
Est. Monthly
$515
HOA / Fees

About This Property

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 cafe, 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.
Unit Size
6,026 Ft²
Days on Market
88 days
Land Size
0.41 acres
Price per sqft
$664
Property Type
House
Property Taxes
$1,903
HOA Dues
$515
Year Built
2002

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Last updated: 6 months ago ( #225084896)

Price History

Date / Event Date Event Price
Mar 31, 2026 Sold
Sold
Mar 2, 2026 In contract -
In contract
Feb 26, 2026 Price Decreased $3,999,000
↓ $496K (11%)
Price Decreased
Jan 2, 2026 Listed by Downing Frye Realty Inc. $4,495,000
Listed by Downing Frye Realty Inc.
Dec 15, 2025 Temporarily off market -
Temporarily off market
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Property Highlights

Garage
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 2002
  • Effective Year Built: 2002
  • Building Count: 1
  • Bedroom Count: 0
  • Building Condition: 0
  • Building Quality: 1
  • Construction Type: 12
  • Building Style: 0
  • Exterior Walls Type: 0
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 0
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 315
  • Parking Space Count: 1
  • Patio Type: 70
  • Porch Type: 0
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 17,860
  • Lot Size Depth Feet: 1,500
  • Lot Size Frontage Feet: 1,200
  • Total Building Area: 4,860
  • Gross Building Area: 4,860
  • Building Area: 4,545
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 0
  • Heating: 0
  • Heated Square Feet: 4,545
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: AUDUBON COUNTRY CLUB #2
  • Land Acres: 0000000410
  • Standard Land Use Code: 1001
  • County Land Use Code: 1
  • State Land Use Code: 01
  • Legal Description 1: AUDUBON COUNTRY CLUB UNIT TWO BLK D LOT 6

Neighborhood

  • School District Name: Collier County School District
  • School Tax School District: DISTRICT 1
  • Census Tract: 010114

Zoning

  • Zoning: PUD

Geography

  • Assessors Map Reference: 3A08
  • Subdivision Tract Number: 170500
  • Parcel: 22510006750
  • Block: D
  • Lot: 6
  • Meridian: SEC 8 TWN 48 RNG 25
  • Municipality: COUNTY COLLIER
  • Latitude: 26.3189
  • Longitude: -81.8241

    Address

  • Full Address: 253 Cheshire Way
  • Legal Unit: 2
  • Address - House Number: 253
  • Address - Street Name: Cheshire
  • Address - Suffix Type: Way
  • State: FL
  • City Name: Naples
  • Carrier Code: R884
  • 4-Digit Zip Code: 4410
  • Zip Code: 34110

Valuation

    Tax

  • Total Area: 6,046
  • Tax Year: 2022
  • Tax Amount: $1,272,430
  • Tax Rate Code Area: 168

    Appraisal Valuation

  • Standard Deviation: 0.4817
  • Valuation Date: Feb 14, 2024
  • Confidence Score: 3
  • Final Value: 1,901,871
  • High Value: 2,818,103
  • Low Value: 985,638

    Market Valuation

  • Market Total Value: $2,538,601
  • Market Land Value: $453,600
  • Market Improvement Value: $2,085,001

    Assessments Valuation

  • Assessed Year: 2022
  • Assessed Total Value: $1,233,386

    Sales

  • Current Sale Contract Date: Apr 01, 2022
  • Current Sale Recording Date: Apr 11, 2022
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 6234214
  • Previous Sale Recording Date: Apr 23, 2018
  • Previous Sale Contract Date: Apr 20, 2018
  • Previous Sale Amount: $1,610,000
  • Previous Sale Document Type: 71
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About North Naples


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Frequently Asked Questions

When was property at 253 Cheshire Way built and last sold?
The property at 253 Cheshire Way was built in 2002 and last sold on Apr 1, 2022 for $3,300,000.
How much is this home worth?
The estimated value of the home located at 253 Cheshire Way is $0.
What are some comparable homes to 253 Cheshire Way?
There are currently no comparable homes to 253 Cheshire Way.