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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
    $3,578,200 Zestimate®
    $597/sqft
    $31,300 Estimated rent

    Home value

    $3,578,200

    $3.22M - $3.97M

    $31,300/mo

    Zestimate® history
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    What's special

    Spectacular golf course backdropDual oversized islandsSouthern golf course viewsPrivate bathsCustom cabinetrySoaring ceilingsPanoramic views
    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.

    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#: 225084896MLS LogoOriginating MLS: Naples

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 6
    • Full bathrooms: 4
    • 1/2 bathrooms: 2
    Rooms
    • Room types: Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Office, Loft, Screened Lanai/Porch, 4 Bedrooms Plus Den
    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 & HOA

    Community
    • Features: Clubhouse, Park, Pool, Fitness Center, Fishing, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
    • Security: Security System, Smoke Detector(s), Gated Community
    • Subdivision: AUDUBON COUNTRY CLUB
    HOA
    • Has HOA: Yes
    • 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
    • HOA fee: $17,030 annually
    Location
    • Region: Naples

    Financial & listing details

    • Price per square foot: $597/sqft
    • Tax assessed value: $3,046,801
    • Annual tax amount: $22,833
    • Date on market: 1/2/2026
    • Lease term: Buyer Finance/Cash

    Price history

    DateEventPrice
    3/31/2026Sold$3,600,000-10%$597/sqft
    Source: SWFLMLS #225084896 Report a problem
    3/1/2026Pending sale$3,999,000$664/sqft
    Source: SWFLMLS #225084896 Report a problem
    2/26/2026Price change$3,999,000-11%$664/sqft
    Source: SWFLMLS #225084896 Report a problem
    1/3/2026Listed for sale$4,495,000$746/sqft
    Source: SWFLMLS #225084896 Report a problem
    12/14/2025Listing removed$4,495,000$746/sqft
    Source: SWFLMLS #225010140 Report a problem
    10/10/2025Price change$4,495,000-5.4%$746/sqft
    Source: SWFLMLS #225010140 Report a problem
    9/9/2025Listed for sale$4,750,000$788/sqft
    Source: SWFLMLS #225010140 Report a problem
    8/1/2025Listing removed$4,750,000$788/sqft
    Source: SWFLMLS #225010140 Report a problem
    6/15/2025Price change$4,750,000-4.9%$788/sqft
    Source: SWFLMLS #225010140 Report a problem
    4/10/2025Price change$4,995,000-4.9%$829/sqft
    Source: SWFLMLS #225010140 Report a problem
    3/7/2025Price change$5,250,000-8.8%$871/sqft
    Source: SWFLMLS #225010140 Report a problem
    2/26/2025Price change$5,755,000-4%$955/sqft
    Source: SWFLMLS #225010140 Report a problem
    2/1/2025Listed for sale$5,995,000+81.7%$995/sqft
    Source: SWFLMLS #225010140 Report a problem
    4/11/2022Sold$3,300,000+0.2%$548/sqft
    Source: Public Record Report a problem
    12/7/2021Pending sale$3,295,000$547/sqft
    Source: SWFLMLS #221082182 Report a problem
    11/30/2021Listed for sale$3,295,000+104.7%$547/sqft
    Source: SWFLMLS #221082182 Report a problem
    4/23/2018Sold$1,610,000-11.8%$267/sqft
    Source: Public Record Report a problem
    3/23/2018Pending sale$1,825,000$303/sqft
    Source: Keller Williams Elite Realty #218007207 Report a problem
    1/30/2018Listed for sale$1,825,000+644.9%$303/sqft
    Source: Keller Williams Elite Realty 2 #218007207 Report a problem
    7/3/2000Sold$245,000$41/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax 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 homes

    Nearby schools

    GreatSchools rating
    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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