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.
Sold for $3,600,000
$3,600,000
253 Cheshire WAY, NAPLES, FL 34110
4beds
6,026sqft
Single Family Residence
Built in 2002
0.41 Acres Lot
$3,593,800 Zestimate®
$597/sqft
$31,300 Estimated rent
Home value
$3,593,800
$3.23M - $3.99M
$31,300/mo
Zestimate® history
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$39,056/mo
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Est. payment
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List your homeWhat's special
Spectacular golf course backdropDual oversized islandsSouthern golf course viewsPrivate bathsCustom cabinetrySoaring ceilingsPanoramic views
Zillow last checked:
Listing updated:
Listed by:
Patti Fortune, PA 239-272-8494,
Downing Frye Realty Inc.
Bought with:
Patti Fortune, PA
Downing Frye Realty Inc.
Source: SWFLMLS,MLS#: 225084896
Originating MLS: Naples
Originating MLS: NaplesFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 6
- Full bathrooms: 4
- 1/2 bathrooms: 2
Bedroom
- Features: Master BR Ground, Master BR Sitting Area
Dining room
- Features: Eat-in Kitchen, Formal
Heating
- Central
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Grill - Gas, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Washer, Wine Cooler
- Laundry: Inside, Laundry Tub
Features
- Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet(s), Window Coverings, Zero/Corner Door Sliders, Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Loft, Screened Lanai/Porch
- Flooring: Marble, Wood
- Doors: Zero/Corner Door Sliders
- Windows: Window Coverings, Impact Resistant Windows, Storm Protection (Other), Shutters Electric
- Has fireplace: Yes
Interior area
- Total structure area: 8,271
- Total interior livable area: 6,026 sqft
Property
Parking
- Total spaces: 3
- Parking features: Circular Driveway, Attached
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Screened Lanai/Porch
- Exterior features: Balcony, Outdoor Grill, Outdoor Kitchen
- Has private pool: Yes
- Pool features: Community, Pool/Spa Combo, In Ground, Custom Upgrades, Gas Heat
- Has spa: Yes
- Spa features: In Ground, Heated, Pool Integrated, Screened
- Has view: Yes
- View description: Golf Course
- Waterfront features: None
- Frontage type: Golf Course
Lot
- Size: 0.41 Acres
- Features: On Golf Course, Oversize
Details
- Additional structures: Cabana, Tennis Court(s), Gazebo, Outdoor Kitchen
- Parcel number: 22510006750
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Frame, Stucco
- Foundation: Concrete Block
- Roof: Tile
Condition
- New construction: No
- Year built: 2002
Utilities & green energy
- Gas: Propane
- Water: Central
Community & neighborhood
Security
- Security features: Security System, Smoke Detector(s), Gated Community
Community
- Community features: Clubhouse, Park, Pool, Fitness Center, Fishing, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Location
- Region: Naples
- Subdivision: AUDUBON COUNTRY CLUB
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $17,030 annually
- Amenities included: 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
Price history
| Date | Event | Price |
|---|---|---|
| 3/31/2026 | Sold | $3,600,000-10%$597/sqft |
Source:  SWFLMLS #225084896 Report a problem | ||
| 3/1/2026 | Pending sale | $3,999,000$664/sqft |
Source: SWFLMLS #225084896 Report a problem | ||
| 2/26/2026 | Price change | $3,999,000-11%$664/sqft |
Source: SWFLMLS #225084896 Report a problem | ||
| 1/3/2026 | Listed for sale | $4,495,000$746/sqft |
Source: SWFLMLS #225084896 Report a problem | ||
| 12/14/2025 | Listing removed | $4,495,000$746/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 10/10/2025 | Price change | $4,495,000-5.4%$746/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 9/9/2025 | Listed for sale | $4,750,000$788/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 8/1/2025 | Listing removed | $4,750,000$788/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 6/15/2025 | Price change | $4,750,000-4.9%$788/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 4/10/2025 | Price change | $4,995,000-4.9%$829/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 3/7/2025 | Price change | $5,250,000-8.8%$871/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 2/26/2025 | Price change | $5,755,000-4%$955/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 2/1/2025 | Listed for sale | $5,995,000+81.7%$995/sqft |
Source: SWFLMLS #225010140 Report a problem | ||
| 4/11/2022 | Sold | $3,300,000+0.2%$548/sqft |
Source: Public Record Report a problem | ||
| 12/7/2021 | Pending sale | $3,295,000$547/sqft |
Source: SWFLMLS #221082182 Report a problem | ||
| 11/30/2021 | Listed for sale | $3,295,000+104.7%$547/sqft |
Source: SWFLMLS #221082182 Report a problem | ||
| 4/23/2018 | Sold | $1,610,000-11.8%$267/sqft |
Source: Public Record Report a problem | ||
| 3/23/2018 | Pending sale | $1,825,000$303/sqft |
Source: Keller Williams Elite Realty #218007207 Report a problem | ||
| 1/30/2018 | Listed for sale | $1,825,000+644.9%$303/sqft |
Source: Keller Williams Elite Realty 2 #218007207 Report a problem | ||
| 7/3/2000 | Sold | $245,000$41/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $24,339 +2.3% | $2,572,153 +3% |
| 2024 | $23,785 +1.5% | $2,497,369 +2.9% |
| 2023 | $23,439 +87.6% | $2,427,921 +96.9% |
| 2022 | $12,493 -1.2% | $1,233,386 +3% |
| 2021 | $12,651 -14.3% | $1,197,462 -14.7% |
| 2020 | $14,760 +1.6% | $1,404,034 +2.3% |
| 2019 | $14,529 +19.9% | $1,372,467 +19% |
| 2018 | $12,122 -1.7% | $1,153,434 +2.1% |
| 2017 | $12,335 +1.4% | $1,129,710 -8.5% |
| 2016 | $12,169 -8.4% | $1,234,006 +1.4% |
| 2015 | $13,290 -0.1% | $1,217,325 +5.2% |
| 2014 | $13,309 -0.2% | $1,157,664 +0.4% |
| 2013 | $13,330 +0.5% | $1,153,476 +1.8% |
| 2012 | $13,270 -4.3% | $1,133,359 -4.9% |
| 2011 | $13,866 -14.6% | $1,191,397 -10.7% |
| 2010 | $16,240 -6.1% | $1,333,433 -6% |
| 2009 | $17,297 | $1,418,996 -14.3% |
| 2008 | $17,297 -7.1% | $1,656,412 -7.5% |
| 2007 | $18,624 +8.1% | $1,791,630 +14.8% |
| 2006 | $17,236 | $1,560,103 +15% |
| 2005 | $17,236 +13.3% | $1,356,992 +14.3% |
| 2004 | $15,212 -1.5% | $1,187,393 +0.9% |
| 2003 | $15,447 +418.2% | $1,177,002 +444.9% |
| 2002 | $2,981 -49.1% | $216,000 |
| 2001 | $5,861 +106.9% | $216,000 |
| 2000 | $2,833 | -- |
Find assessor info on the county website
Neighborhood: 34110
Nearby schools
GreatSchools rating
- 7/10Naples Park Elementary SchoolGrades: PK-5Distance: 3.2 mi
- 10/10North Naples Middle SchoolGrades: 6-8Distance: 3.8 mi
- 6/10Aubrey Rogers High SchoolGrades: 9-12Distance: 2.8 mi
Schools provided by the listing agent
- Elementary: NAPLES PARK
- Middle: NORTH NAPLES
- High: AUBREY ROGERS
Source: SWFLMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Florida
- Collier County
- Naples
- 34110
- 253 Cheshire WAY
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