253 Cheshire Way
Description
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—turnkey and move-in ready. 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...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—turnkey and move-in ready. 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. 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.
- Listed by Patti Fortune, PA • Downing Frye Realty Inc.
Property Details for 253 Cheshire Way
Property Details for 253 Cheshire Way
| Status | Active |
|---|---|
| MLS # | 225084896 |
| Days on Market | 12 |
| Taxes | $22,833 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Residential / Single Family |
| Year Built | 2002 |
| Lot Size | 0.41 AC / 17,859 SF |
| County | Collier County |
Location
Building Information for 253 Cheshire Way
Payment Calculator
$23,811 per month
30 year fixed, 6.15% Interest
$21,908
$1,903
$0
Property Information for 253 Cheshire Way
- 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), Underground Utility
- Community Type: Clubhouse, Park, Pool, Fitness Center, Fishing, Golf Course, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis, Gated
- Elementary School: NAPLES PARK
- Golf Type: Golf Non Equity
- High School: AUBREY ROGERS
- Middle School: NORTH NAPLES
- Pets: No Approval Needed
- Status Type: Resale Property
- Frontage Type: Golf Course
- Carport Desc: Circular Driveway, Attached
- Carport Spaces: 0
- Attached Garage: Yes
- Garage Spaces: 3
- Carport: No
- Covered Spaces: 3
- Garage: Yes
- Total Parking: 3
- HOA Desc: Yes
- HOA Fee: $.00
- Condo Fee: $0
- Primary HOA Fee: $8,575
- Primary HOA Fee Freq: Annually
- Total Annual Recurring Fees: $19,430.00
- Tax Annual Amount: $22,833.04
- Virtual Tour URL Branded: https://lacasatour.com/property/253-cheshire-way-naples-fl-34110/ub
- Virtual Tour URL Unbranded: https://lacasatour.com/property/253-cheshire-way-naples-fl-34110/ub
- Laundry Features: Laundry in Residence, Laundry Tub
- Approx Living Area: 6026.0
- Living Area Units: Square Feet
- Bedroom Desc: Master BR Ground,Master BR Sitting Area
- Bedrooms: 4+Den
- Dining Description: Eat-in Kitchen,Formal
- Elevator: None
- Appliances: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Grill - Gas, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Washer, Wine Cooler
- Equipment: Auto Garage Door, Cooktop - Gas, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Generator, Grill - Gas, Home Automation, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Security System, Smoke Detector, Washer, Wine Cooler
- Flooring: Marble, Wood
- Interior Features: Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet, Window Coverings, Zero/Corner Door Sliders
- Spa Features: Below Ground, Heated Gas, Pool Integrated, Screened
- Private Pool Desc: Community, Pool/Spa Combo, Below Ground, Custom Upgrades, Gas Heat
- Private Pool: Yes
- Private Spa: Yes
- Room Count: 0
- Total Floors: 2
- Baths Full: 4
- Half Bathrooms: 2
- Bathrooms Total Decimal: 5.00
- Bathrooms: 6
- Bedrooms Total: 4
- Door Features: Zero/Corner Door Sliders
- Fireplace: Yes
- Foundation Details: Concrete Block
- Other Equipment: Generator
- View YN: Yes
- Floor Plan Type: 2 Story
- Additional Rooms: Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Loft, Screened Lanai/Porch
- Gas: Yes
- Exterior Features: Balcony, Screened Lanai/Porch, Built In Grill, Outdoor Kitchen, Cabana, Tennis Court(s), Gazebo, Patio
- Exterior Finish: Concrete Block, Wood Frame, Stucco
- Roof: Tile
- Windows: Window Coverings
- Storm Protection: Impact Resistant Windows, Other, Shutters Electric
- Cooling: Ceiling Fan(s), Central Electric
- Cooling YN: Yes
- Heat: Central Electric
- Heating YN: Yes
- Irrigation: Other
- Water: Central
- Gas: Propane
- Structure Type: House
- Lease Limits YN: Yes
- Horse: No
- Lease Term: Buyer Finance/Cash
- Transfer Fee: $3,700.00
- Leases Per Year: 2
- Min Days of Lease: 60
Property History for 253 Cheshire Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jan 2, 2026 | Listed (Active) Naples Area Board of REALTORS #225084896 | $4,495,000 | — |
| Dec 14, 2025 | Withdrawn Naples Area Board of REALTORS #225010140 | — | |
| Dec 14, 2025 | Temporarily Off Market Naples Area Board of REALTORS #225010140 | — | |
| Jun 15, 2025 | Price Change Naples Area Board of REALTORS #225010140 | $4,750,000 | — |
| Apr 10, 2025 | Price Change Naples Area Board of REALTORS #225010140 | $4,995,000 | — |
| Mar 6, 2025 | Price Change Naples Area Board of REALTORS #225010140 | $5,250,000 | — |
| Feb 25, 2025 | Price Change Naples Area Board of REALTORS #225010140 | $5,755,000 | — |
| Feb 1, 2025 | Listed (Active) Naples Area Board of REALTORS #225010140 | $5,995,000 | — |
| Apr 1, 2022 | Sold Naples Area Board of REALTORS #221082182 | $3,300,000 | — |
| Mar 31, 2022 | Sold (Public Record) Public Record #1487384685 | $3,300,000 | +20.0% / yr |
| Jan 11, 2022 | Temporarily Off Market BEARMLS #221082182 | — | |
| Jan 11, 2022 | Pending Naples Area Board of REALTORS #221082182 | — | |
| Jan 11, 2022 | Pending BEARMLS #221082182 | — | |
| Dec 7, 2021 | Pending With Contingencies Naples Area Board of REALTORS #221082182 | — | |
| Nov 30, 2021 | Listed (Active) BEARMLS #221082182 | $3,295,000 | — |
| Nov 30, 2021 | Listed (Active) Naples Area Board of REALTORS #221082182 | $3,295,000 | — |
| Apr 20, 2018 | Sold (Public Record) Public Record #620966894 | $1,610,000 | — |
| Apr 20, 2018 | Sold Naples Area Board of REALTORS #218007207 | $1,610,000 | — |
| Apr 11, 2018 | Pending Naples Area Board of REALTORS #218007207 | — | |
| Mar 17, 2018 | Pending With Contingencies Naples Area Board of REALTORS #218007207 | — | |
| Jan 29, 2018 | Listed (Active) Naples Area Board of REALTORS #218007207 | $1,825,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 01/02/2026 | Listed (Active) Naples Area Board of REALTORS #225084896 | $4,495,000 |
| 12/14/2025 | Withdrawn Naples Area Board of REALTORS #225010140 | — |
| 12/14/2025 | Temporarily Off Market Naples Area Board of REALTORS #225010140 | — |
| 06/15/2025 | Price Change Naples Area Board of REALTORS #225010140 | $4,750,000 |
| 04/10/2025 | Price Change Naples Area Board of REALTORS #225010140 | $4,995,000 |
| 03/06/2025 | Price Change Naples Area Board of REALTORS #225010140 | $5,250,000 |
| 02/25/2025 | Price Change Naples Area Board of REALTORS #225010140 | $5,755,000 |
| 02/01/2025 | Listed (Active) Naples Area Board of REALTORS #225010140 | $5,995,000 |
| 04/01/2022 | Sold Naples Area Board of REALTORS #221082182 | $3,300,000 |
| 03/31/2022 | Sold (Public Record) Public Record #1487384685 | $3,300,000 +20.0% / yr |
| 01/11/2022 | Temporarily Off Market BEARMLS #221082182 | — |
| 01/11/2022 | Pending Naples Area Board of REALTORS #221082182 | — |
| 01/11/2022 | Pending BEARMLS #221082182 | — |
| 12/07/2021 | Pending With Contingencies Naples Area Board of REALTORS #221082182 | — |
| 11/30/2021 | Listed (Active) BEARMLS #221082182 | $3,295,000 |
| 11/30/2021 | Listed (Active) Naples Area Board of REALTORS #221082182 | $3,295,000 |
| 04/20/2018 | Sold (Public Record) Public Record #620966894 | $1,610,000 |
| 04/20/2018 | Sold Naples Area Board of REALTORS #218007207 | $1,610,000 |
| 04/11/2018 | Pending Naples Area Board of REALTORS #218007207 | — |
| 03/17/2018 | Pending With Contingencies Naples Area Board of REALTORS #218007207 | — |
| 01/29/2018 | Listed (Active) Naples Area Board of REALTORS #218007207 | $1,825,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 253 Cheshire Way
Schools near 253 Cheshire Way
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 11 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Naples Park Elementary School PublicPK to 5 | ||
North Naples Middle School Public6 to 8 | ||
Aubrey Rogers High School Public9 to 11 | ||
Florida Virtual Course Offerings Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Downing Frye Realty Inc., Patti Fortune, PA
The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.
