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  • $1,025,000

    23 Winewood Ct, Fort Myers, FL 33919

    4beds
    5,300sqft
    Single Family Residence
    Built in 1991
    0.42 Acres Lot
    $1,024,800 Zestimate®
    $193/sqft
    $5,826 Estimated rent

    Home value

    $1,024,800

    $922,000 - $1.15M

    $5,826/mo

    Zestimate® history
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    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Cookie Kermer Douglas 239-410-1929,

    John R. Wood Properties

    Bought with:

    Samantha Bagdasarian, 258025879

    EXP Realty LLC

    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

    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: IrrigationSprinklers, 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: $193/sqft
    • Tax assessed value: $1,099,718
    • Annual tax amount: $8,541
    • Date on market: 8/31/2026
    • Cumulative days on market: 39 days
    • Listing terms: All Financing Considered,Cash
    • Ownership: Single Family
    • Contingency: Inspection

    Price history

    DateEventPrice
    10/9/2026Sold$1,025,000-6.8%$193/sqft
    Source: Florida Gulf Coast MLS #2026036646 Report a problem
    9/8/2026Pending sale$1,100,000$208/sqft
    Source: Florida Gulf Coast MLS #2026036646 Report a problem
    8/31/2026Listed for sale$1,100,000$208/sqft
    Source: Florida Gulf Coast MLS #2026036646 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

    Neighborhood: 33919

    Nearby schools

    GreatSchools rating
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    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
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    With Zillow Showcase(estimated)

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