About 253 Cheshire Way
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.
Features of 253 Cheshire Way
| MLS® # | 225084896 |
|---|---|
| Price | $3,999,000 |
| Sold Price | $3,600,000 |
| Bedrooms | 4 |
| Bathrooms | 6.00 |
| Full Baths | 4 |
| Half Baths | 2 |
| Square Footage | 6,026 |
| Acres | 0.41 |
| Year Built | 2002 |
| Type | Residential |
| Sub-Type | Single Family |
| Style | Two Story, Single Family |
| Status | Closed |
Community Information
| Address | 253 Cheshire Way |
|---|---|
| Area | NA01 - N/O 111th Ave Bonita Beach |
| Subdivision | AUDUBON COUNTRY CLUB |
| City | NAPLES |
| County | Collier |
| State | FL |
| Zip Code | 34110 |
| Community Type | Gated, Golf Course, Tennis |
Amenities
| 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 |
|---|---|
| Parking | Circular Driveway, Attached |
| # of Garages | 3 |
| Garages | Attached |
| View | Golf Course |
| Is Waterfront | No |
| Pets Allowed | No Approval Needed |
| Waterfront | None |
| Has Pool | Yes |
| Pool | Community, Pool/Spa Combo, Below Ground, Custom Upgrades, Gas Heat |
| Elevator | None |
Interior
| Interior Features | Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet(s), Window Coverings, Zero/Corner Door Sliders |
|---|---|
| Appliances | Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Grill - Gas, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Washer, Wine Cooler |
| Heating | Central Electric |
| Cooling | Ceiling Fan(s), Central Electric |
| Fireplace | Yes |
Exterior
| Exterior | Concrete Block, Wood Frame, Stucco |
|---|---|
| Exterior Features | Balcony, Screened Lanai/Porch, Built In Grill, Outdoor Kitchen |
| Lot Description | Golf Course, Oversize |
| Windows | Window Coverings |
| Roof | Tile |
| Construction | Concrete Block, Wood Frame, Stucco |
School Information
| Elementary | NAPLES PARK |
|---|---|
| Middle | NORTH NAPLES |
| High | AUBREY ROGERS |
Additional Information
| Date Listed | January 2nd, 2026 |
|---|---|
| Date Sold | March 31st, 2026 |
| Days on Market | 251 |
| Foreclosure | No |
| Short Sale | No |
| Annual Recurring Fees | $17,030 |
Listing Details
| Office | Downing Frye Realty Inc. |
|---|