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253 Cheshire WAY
NAPLES, FL 34110

$4,495,000

Beds: 4
Baths: 4 | 2
Sq. Ft.: 6,026
Type: House
Listing #225084896
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. 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.
Property Features
Location Information
County: Collier
Development: AUDUBON
MLS Area: NA01 - N/O 111th Ave Bonita Beach
Community: Gated, Golf Course, Tennis
Latitude: 26.318953
Longitude: -81.824076
Subdivision: AUDUBON COUNTRY CLUB
Interior Features
Rooms: Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Loft, Screened Lanai/Porch
Interior: Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet(s), Window Coverings, Zero/Corner Door Sliders
1/2 Baths: 2
Dining Room Description: Eat-in Kitchen, Formal
Heating: Central Electric
Cooling: Ceiling Fan(s), Central Electric
Floors: Marble, Wood
Equipment: Generator
Total Number of Units: 1
Windows/Doors Description: Window Coverings
Exterior Features
Style: 2 Story
Stories: 2
Construction: Concrete Block, Wood Frame, Stucco
Exterior: Balcony, Screened Lanai/Porch, Built In Grill, Outdoor Kitchen
Roof: Tile
Garage Description: 3, Circular Driveway, Attached
Irrigation: Other
Pool Description: Community, Pool/Spa Combo, Below Ground, Custom Upgrades, Gas Heat
Lot Description: Golf Course, Oversize
Lot Size in Acres: 0.41
Storm Protection: Impact Resistant Windows, Other, Shutters Electric
Rear Exposure: S
Waterfront Description: None
View Description: Golf Course
School
Elementary School: NAPLES PARK
Middle School: NORTH NAPLES
High School: AUBREY ROGERS
Additional Information
Property Type: SFR
Property SubType: Single Family
Building Design: Single Family
Year Built: 2002
Status: Active
HOA Fee: $8,575
HOA Frequency: Annually
Additional Fees: Mandatory Club Fee: 10855, Mandatory Club Fee Frequency: Annually
One Time Fees: Mandatory Club Fee: 10855, Transfer Fee: 3700
Restrictions: Deeded
Pets: Yes
Boat Access: None
Spa Description: Below Ground, Heated Gas, Pool Integrated, Screened
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
Maintenance: Cable, Internet/WiFi Access, Legal/Accounting, Manager, Master Assn. Fee Included, Reserve, Security, Street Lights, Street Maintenance
Tax Year: 2024
Tax Amount: $22,833.04
Original List Price: 4495000

Listing Courtesy of: Downing Frye Realty Inc. Co-listing agent:
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The data relating to real estate for sale on this limited electronic display come in part from the Broker Reciprocity Program (BR Program) of the Bonita Springs-Estero Association of REALTORS®, Florida Gulf Coast Multiple Listing Service, Inc., and the M.L.S. of Naples, Inc. Properties listed with brokerage firms other than ShellStar Realty are marked with the BR Icon and detailed information about them includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties available through the BR Program.
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Southwest Florida data last updated at January 23, 2026, 5:43 PM ET