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$4,495,000
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Property Description
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.
Full Property Details
Full Property Details for 253 Cheshire Way
General
- Price: $4,495,000
- Taxes: (2024)
- Status: Active
- Type: Single Family
- Source: Bonita_Springs
- MLS ID: 225084896
- Updated: 1/3/2026
- Added to Site: 16 day(s) ago
Rental Information
- Lease/Rent Term: 60
- Min. Lease (Days): 60
Interior
- Interior Features: Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Loft, Entrance Foyer, Volume Ceiling, Walk-In Closet(s)
- Fireplace: Yes
- Appliances: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Microwave, Range, Refrigerator with Icemaker, Reverse Osmosis, Washer, Wine Cooler
- Furnishings: Negotiable
- Flooring: Marble, Wood
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 4
- Half Bathrooms: 2
- Primary Bathroom: 2 Masters, Multiple Shower Heads, Separate Tub And Shower
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Master BR Sitting Area, Master BR Ground
Other Rooms
- Dining Room: Eat-in Kitchen, Formal
- Laundry: Inside, Sink
Additional Information
- Shared Amenities: Golf Non Equity, Bocce Court, Cabana, Clubhouse, Park, Pool, Community Room, Fitness Center, Fishing, Golf, Internet Access, Library, Pickleball, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated, Golf Course, Tennis
- Pool: Yes
- Private Pool: Yes
- Pool Description: Community Lap Pool, In Ground, Custom Upgrades, Gas Heat
- Spa: Yes
- Spa Description: In Ground, Heated (Gas), Integrated with Pool, Screened
- Tennis: Yes
- Security/Safety: Security System, Smoke Detector(s)
- Equipment: Generator, Home Automation
Exterior
- Exterior Features: Gas Grill, Balcony, Outdoor Grill, Outdoor Kitchen, Automatic Sprinkler
- Porch/Patio/Deck: Screened Lanai/Porch, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Circular Driveway, Garage Door Opener, Attached
Location
- Area: NA01 - N/O 111th Ave Bonita Beach
- County: Collier
- Subdivision: AUDUBON COUNTRY CLUB
- Building Name: AUDUBON
- Driving Directions: Use the Vanderbilt west entrance. Show the gatehouse your business card and have clients in your car or directly behind you.
- Direction Faces: North
School Information
- Elementary School: NAPLES PARK
- Middle School: NORTH NAPLES
- High School: AUBREY ROGERS
Community
- Association: Yes
- Assoc. Fees Include: Cable TV, Internet, Legal/Accounting, Manager, Master Assn. Fee Included, Reserve, Security, Street Lights, Street Maintenance
- Units Assoc/Comm: 1
- Pets Allowed: Yes
- Management Type: Professional
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Ceiling Fan(s), Central Electric
- Heating Type: Central Electric, Fireplace(s)
Utilities
- Gas: Propane
- Sewer: Central
- Water: Central
- Cable Available: Yes
- Utility Description: Underground Utilities, Propane, Cable Available
Structural Information
- Description/Design: Single Family Residence
- Exterior Const.: Concrete Block, Wood Frame, Stucco
- Roof: Tile
- Windows: Impact Resistant, Single Hung, Impact Resistant Windows, Shutters Electric, Window Coverings
- Doors: Zero/Corner Door Sliders
- Stories/Levels: 2
- Stories in Building: 2
- Square Feet: 6,026
- Sq. Ft. Source: Property Appraiser Office
- Living Area: 6,026 Sq. Ft.
- Year Built: 2002
Additional Structures
- Other Structures: Gazebo
Lot Features
- Property View: Golf Course
- Lot Size (Acres): 0.41
- Lot Size (Sq. Ft.): 17,859
- Lot Size Source: Property Appraiser Office
- Lot Dimensions: 150 x 150 x 120 x 120
- Frontage: Private Road
- Frontage Feet: 150
- Irrigation System: Other
- Lot Features: On Golf Course, Oversize
- Lot Description: On Golf Course, Oversize
Water Features
- Water Front Desc.: None
- Canal Width: None
Financial Considerations
- Other Assoc Fees: $8,575
- Mand. Club Fee: $10,855
- Mand. Club Fee Freq: Annually
- One Time Club Fee: $92,500
- Application Fee: $150
- Other Fee Freq.: Annually
- Tax Year: 2024
- Terms: Buyer Finance/Cash
Disclosures and Reports
- Ownership: Single Family
- Legal Description: AUDUBON COUNTRY CLUB UNIT TWO BLK D LOT 6
- Property ID: 22510006750
- Section: 8
- Block: D
- Lot Number: 6
Listed by Downing Frye Realty Inc.
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Schools
Schools serving 253 Cheshire Way
School District:Collier County School District
| Name | Grades | Distance |
|---|---|---|
Naples Park Elementary School 685 111th Avenue North, Naples, FL 34108 | PK-5 | 3.2 mi |
North Naples Middle School 16165 Learning Lane, Naples, FL 34110 | 6-8 | 3.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 253 Cheshire Way
Date
Details
Price
Change
Source
1/02/2026
Listed
$4,495,000
36.21%
MLS
3/31/2022
Sold
$3,300,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 253 Cheshire Way
Year
Property Taxes
Change
Tax Assessment
Change
2025
$24,339
2%
$2,572,153
3%
2024
$23,785
—
$2,497,369
3%
2023
$23,688
84%
$2,427,921
103%
2021
$12,877
1%
$1,197,462
-3%
2022
$12,724
-1%
$1,233,386
-12%
2021
$12,877
-13%
$1,404,034
2%
2019
$14,746
20%
$1,372,467
19%
2018
$12,335
1%
$1,153,434
2%
2017
$12,169
-8%
$1,129,710
-8%
2016
$13,290
—
$1,234,006
1%
2015
$13,309
1%
$1,217,325
1%
2014
$13,163
-1%
$1,207,664
—
2013
$13,330
—
$1,203,476
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 253 Cheshire Way
253 Cheshire Way, Naples, FL 34110 (MLS# 225084896) is a Single Family property with 4 bedrooms, 4 full bathrooms and 2 partial bathrooms. 253 Cheshire Way is currently listed for $4,495,000 and was received on January 02, 2026. Want to learn more about 253 Cheshire Way? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.

