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For sale
  • $2,995,000

    268 Cheshire WAY, NAPLES, FL 34110

    4beds
    3,979sqft
    : 
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    Single Family Residence
    Built in 2005
    0.39 Acres Lot
    $2,723,200 Zestimate®
    $753/sqft
    $1,411/mo HOA

    What's special

    Golf course beyondBeautifully renovated kitchenExpansive lanaiFenced dog runDistinguished study
    This casually elegant residence combines luxury and nature in the prestigious Audubon Golf and Country Club, a rare offering west of 41. The entrance opens to stunning views through the living spaces onto an expansive lanai, a pool framed by lush landscaping, and the golf course beyond. The outdoor sanctuary blends seamlessly with generous living spaces, beautifully renovated kitchen, and family room, creating an entertainer’s delight! The inviting layout is framed by a large bay window and sliding glass doors that open to the spectacular lanai and pool. The lanai showcases a newly resurfaced saltwater pool and spa with new pool equipment and propane heater, and a stunning new marble pool deck installed in 2025. Complementing the protection provided by 2006 construction standards and impact windows, newly installed MagnaTrack hurricane-rated screens controlled by a controller or through an app provide security while preserving the view of the 13th green of the Signature Joe Lee 18-hole golf course without compromising privacy. An outdoor shower adds to the resort-inspired living. A fenced dog run and professional landscaping complete the redesigned grounds. With resiliency in mind, the home features a new roof and solar panels installed in 2024 with four Tesla Powerwall batteries to generate more electricity than the house uses from the electric grid. The system provides resiliency during power outages without the need for a generator. Inside, four large bedrooms, each with its own private en-suite bathroom, a distinguished study, and a powder room opening onto the lanai complete the house. A Sonos sound system in the living room, family room, and primary suite provide entertainment. The generous 1,224 sq ft garage has room for up to 6 vehicles. The scenic community spreads across 755 acres, with 58% certified as a nature preserve and 28 lakes woven throughout. The main clubhouse offers both formal and casual dining, along with a card room for Bridge, Mah Jongg, Canasta, and more. The recently built Lifestyle Center houses the Courtside Café, an open-air dining venue overlooking the 25-meter heated lap pool. The state-of-the-art 10,000 square foot Fitness Center featuring Technogym cardio and weight machines offers personal training, exercise and Pilates classes, physical therapy, and massage services. Newly renovated and expanded tennis, pickleball, and bocce courts, along with a renovated croquet lawn, complete the sports opportunities. The natural setting of the community is complemented by the bayside Boardwalk, an idyllic setting for sunset strolls, winding its way through marsh teeming with wildlife to Little Hickory Bay, a dedicated kayak and paddleboard launch, all within walking distance from this home. Redefined, private, and thoughtfully curated at every turn, this is a legacy property designed for those who expect nothing less than exceptional.
    140 days
    |
    374
    |
    6
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Nikki Dimitrova 239-537-3671,

    Florida Prime Realty, LLC,

    Spase Dimitrov 239-537-3666,

    Florida Prime Realty, LLC

    Source: SWFLMLS,MLS#: 226007342MLS LogoOriginating MLS: Naples

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Den - Study, Family Room, Great Room, Guest Bath, Guest Room, Office, Screened Lanai/Porch, 4 Bedrooms Plus Den
      Bedroom
      • Features: Split Bedrooms
      Dining room
      • Features: Dining - Living, Eat-in Kitchen, Formal
      Kitchen
      • Features: Island, Pantry
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Oven, Washer, Wine Cooler
      • Laundry: Inside
      Features
      • Fireplace, Pantry, Wired for Sound, Vaulted Ceiling(s), Volume Ceiling, Window Coverings, Zero/Corner Door Sliders, Den - Study, Family Room, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Screened Lanai/Porch
      • Flooring: Carpet, Tile
      • Doors: Zero/Corner Door Sliders
      • Windows: Window Coverings, Impact Resistant Windows, Shutters Electric
      • Has fireplace: Yes
      Interior area
      • Total structure area: 6,054
      • Total interior livable area: 3,979 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 6
      • Parking features: Circular Driveway, Driveway, Attached
      • Attached garage spaces: 6
      • Has uncovered spaces: Yes
      Features
      • Stories: 1
      • Patio & porch: Patio, Screened Lanai/Porch
      • Exterior features: Outdoor Shower
      • Has private pool: Yes
      • Pool features: Community, In Ground, Concrete, Equipment Stays, Gas Heat, Pool Bath, Salt Water, Screen Enclosure
      • Has spa: Yes
      • Spa features: In Ground, Concrete, Equipment Stays, Heated, Pool Bath, Screened, Bath
      • Fencing: Fenced
      • Has view: Yes
      • View description: Golf Course
      • Waterfront features: None
      Lot
      • Size: 0.39 Acres
      • Features: Regular
      Details
      • Additional structures: Tennis Court(s)
      • Parcel number: 22510006404

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Concrete Block
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Gas: Propane
      • Water: Central
      Green energy
      • Energy generation: Solar

      Community & HOA

      Community
      • Features: Clubhouse, Pool, Fitness Center, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
      • Security: Security System, Gated Community
      • Subdivision: AUDUBON COUNTRY CLUB
      HOA
      • Has HOA: Yes
      • Amenities included: Bocce Court, Clubhouse, Pool, Fitness Center, Golf Course, Library, Pickleball, Private Membership, Putting Green, Restaurant, Shopping, Sidewalk, Streetlight, Tennis Court(s)
      • HOA fee: $16,930 annually
      Location
      • Region: Naples

      Financial & listing details

      • Price per square foot: $753/sqft
      • Tax assessed value: $2,328,141
      • Annual tax amount: $10,473
      • Date on market: 2/16/2026
      • Lease term: Buyer Finance/Cash

        Estimated market value

        $2,723,200

        $2.59M - $2.86M

        $17,500/mo

        Price history

        DateEventPrice
        2/16/2026Listed for sale$2,995,000+199.5%$753/sqft
        Source: SWFLMLS #226007342 Report a problem
        6/16/2020Sold$1,000,000-13.8%$251/sqft
        Source: Public Record Report a problem
        4/25/2020Pending sale$1,159,900$292/sqft
        Source: Keller Williams Elite Realty 2 #220026276 Report a problem
        1/23/2020Price change$1,159,900-1.7%$292/sqft
        Source: Keller Williams Elite Realty 2 #219036483 Report a problem
        10/31/2019Price change$1,179,900-1.7%$297/sqft
        Source: Keller Williams Elite Realty 2 #219036483 Report a problem
        7/17/2019Listed for sale$1,199,900+6.7%$302/sqft
        Source: Keller Williams Elite Realty 2 #219036483 Report a problem
        6/4/2014Sold$1,125,000-5.9%$283/sqft
        Source: Public Record Report a problem
        3/19/2014Listed for sale$1,195,000+359.6%$300/sqft
        Source: Audubon Properties, Inc. #214016886 Report a problem
        2/17/2004Sold$260,000+30%$65/sqft
        Source: Public Record Report a problem
        9/24/2003Sold$200,000$50/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,711 +2.3%$1,138,503 +2.9%
        2024$10,473 +3.1%$1,106,417 +3%
        2023$10,156 -3.3%$1,074,191 +3%
        2022$10,500 -1.2%$1,042,904 +3%
        2021$10,631 -10.8%$1,012,528 -5.4%
        2020$11,912 +12.4%$1,070,334 +10%
        2019$10,596 -12.6%$973,031 -12.8%
        2018$12,128 -1.7%$1,115,580 +1.2%
        2017$12,341 +0.4%$1,102,557 +6.8%
        2016$12,292 +6.9%$1,032,210 +0.3%
        2015$11,496 -1.2%$1,029,305 +10%
        2014$11,637 +6.1%$935,591 -1.2%
        2013$10,967 +0.5%$946,847 +1.8%
        2012$10,916 -4.8%$930,184 -5.4%
        2011$11,470 -15.8%$983,485 -11.9%
        2010$13,621 -2.3%$1,116,582 -6%
        2009$13,943 $1,188,273 -11.5%
        2008$13,943 -6.3%$1,342,646 +3%
        2007$14,883 +413.9%$1,303,540 +2.5%
        2006$2,896 $1,271,746 +457.8%
        2005$2,896 +37.7%$228,000 +38.9%
        2004$2,103 -13.2%$164,160 -11.1%
        2003$2,424 -4.9%$184,680
        2002$2,549 -49.1%$184,680
        2001$5,011 +106.9%$184,680
        2000$2,422 --

        Find assessor info on the county website

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        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34110

        Getting around

        0 / 100
        Car-Dependent
        28 / 100
        Somewhat Bikeable

        Nearby schools

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