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  • $1,100,000

    23 Winewood Ct, Fort Myers, FL 33919

    4beds
    5,300sqft
    : 
    $7,100/mo
    Get pre-qualified
    Single Family Residence
    Built in 1991
    0.42 Acres Lot
    $1,019,900 Zestimate®
    $208/sqft
    $149/mo HOA

    What's special

    Private poolBay-window sitting areaDramatic wood staircaseRear brick patioBreakfast nookSpacious primary suiteOversized lot
    ONE-OF-A-KIND FORT MYERS ESTATE — PRICED TO PERSONALIZE! Welcome to this seldom found, one-owner custom-built colonial style estate, tucked away in one of Fort Myers’ most prestigious hidden neighborhoods. Situated at the end of a quiet cul-de-sac on an oversized lot, this impressive pool home offers over 5,000 sq. ft. of living space, 4 spacious bedrooms, 2 offices/den spaces, 3 full baths, 2 half baths, beautiful real wood floors, a circular driveway with 3-car garage, and a private pool. The grand two-story foyer opens to an oversized living room featuring a wood-burning fireplace and dramatic wood staircase—a truly memorable setting for holiday gatherings. The spacious primary suite includes a bay-window sitting area and French doors leading to the rear brick patio. Above, a conveniently located office/exercise room provides additional flexibility and could easily accommodate a variety of lifestyle needs. Another generously sized office/den on the main level offers even more space for working from home, hobbies, or guests. The expansive kitchen with wood cabinetry and breakfast nook overlooks the family room, where a wall of glass sliders opens to the pool and outdoor entertaining area with easy access to ½ pool bath. Adjacent to the kitchen, the formal dining room has been creatively enjoyed as a music room, offering yet another example of the home’s versatility and ability to adapt to your lifestyle. Upstairs offers 3 additional bedrooms, 2 baths, and a versatile bonus room ideal for a media room, playroom, gym, or guest space. Priced to accommodate your vision and individual tastes, this well-loved home offers an exceptional opportunity to transform a custom estate into your dream home. Enjoy community amenities including tennis, pickleball, dog park, playground, and BBQ/picnic areas etc. All conveniently located near top-rated schools, shopping, beaches, hospitals, and I-75, this remarkable property offers the best of both worlds—the grandeur and privacy of an estate home with easy access to everything Fort Myers has to offer. Ready to make memories for generations.
    6 days
    730
    59

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Cookie Kermer Douglas 239-410-1929,

    John R. Wood Properties

    Source: Florida Gulf Coast MLS,MLS#: 2026036646MLS LogoOriginating MLS: Florida Gulf Coast

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 3
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Den, Exercise Room, Family Room
      Heating
      • Central, Electric
      Cooling
      • Central Air, Ceiling Fan(s), Electric
      Appliances
      • Included: Dryer, Dishwasher, Microwave, Refrigerator, Washer
      • Laundry: Washer Hookup, Dryer Hookup, Inside, Laundry Tub
      Features
      • Built-in Features, Breakfast Area, Separate/Formal Dining Room, Dual Sinks, Entrance Foyer, French Door(s)/Atrium Door(s), Fireplace, High Ceilings, Main Level Primary, Sitting Area in Primary, Shower Only, Separate Shower, Walk-In Closet(s), Den, Exercise Room, Family Room
      • Flooring: Carpet, Tile, Wood
      • Doors: French Doors
      • Windows: Other, Sliding
      • Has fireplace: Yes
      Interior area
      • Total structure area: 6,473
      • Total interior livable area: 5,300 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached, Circular Driveway, Garage, Garage Door Opener
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Exterior features: Sprinkler/Irrigation, None, Other
      • Has private pool: Yes
      • Pool features: In Ground
      • Has view: Yes
      • View description: Landscaped
      • Waterfront features: None
      Lot
      • Size: 0.42 Acres
      • Features: Cul-De-Sac, Oversized Lot, Sprinklers Automatic
      Details
      • Parcel number: 034524P302200.0430
      • Lease amount: $0
      • Zoning description: AA

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Two Story
      • Property subtype: Single Family Residence
      Materials
      • Brick, Stucco, Wood Frame
      • Roof: Shingle
      Condition
      • Resale
      • Year built: 1991

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Features: Gated
      • Condo and coop fee: $0
      • Membership fee: $0
      • Subdivision: CARILLON WOODS
      HOA
      • Has HOA: Yes
      • Amenities included: Dog Park, Barbecue, Picnic Area, Pickleball, Tennis Court(s), Management
      • Services included: Association Management, Recreation Facilities
      • HOA fee: $1,791 annually
      • HOA phone: 239-344-8733
      Location
      • Region: Fort Myers

      Financial & listing details

      • Price per square foot: $208/sqft
      • Tax assessed value: $1,099,718
      • Annual tax amount: $8,541
      • Date on market: 8/31/2026
      • Cumulative days on market: 7 days
      • Listing terms: All Financing Considered,Cash
      • Ownership: Single Family

        Estimated market value

        $1,019,900

        $969,000 - $1.07M

        $4,008/mo

        Price history

        DateEventPrice
        8/31/2026Listed for sale$1,100,000+1366.7%$208/sqft
        Source: Florida Gulf Coast MLS #2026036646 Report a problem
        2/1/1988Sold$75,000$14/sqft
        Source: Agent Provided Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,541 +2.3%$510,026 +2.9%
        2024$8,351 +1.6%$495,652 +3%
        2023$8,223 +0.5%$481,216 +3%
        2022$8,181 -2.1%$467,200 +3%
        2021$8,353 -0.9%$453,592 +1.4%
        2020$8,430 +0.6%$447,329 -41.6%
        2019$8,383 $765,513 +78.4%
        2018$8,383 +1.8%$429,119 +2.1%
        2017$8,237 -0.3%$420,293 -42.1%
        2016$8,263 +2.4%$725,735 +14.3%
        2015$8,072 -0.6%$635,192 +8.2%
        2014$8,123 +0.7%$587,001 +12.7%
        2013$8,063 +4.5%$520,949 +29.9%
        2012$7,714 +3.5%$401,105 -20.4%
        2011$7,454 +0%$503,657 +36.1%
        2010$7,451 -6.4%$370,110 -20.7%
        2009$7,957 +7.8%$466,860 -30%
        2007$7,380 -2.7%$667,370 +2.5%
        2006$7,582 -5.5%$651,410 +26.2%
        2004$8,023 -3.6%$516,060 +13.2%
        2003$8,322 +4.1%$456,020 +1.8%
        2002$7,991 $448,130 +15.1%
        2000-- $389,370
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 33919

        Getting around

        7 / 100
        Car-Dependent
        53 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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