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For sale
    • $799,000

    950 S KENTUCKY AVENUE, WINTER PARK, FL 32789

    4beds
    2,155sqft
    : 
    $5,287/mo
    Get pre-qualified
    Single Family Residence
    Built in 1941
    7,890 Square Feet Lot
    $-- Zestimate®
    $371/sqft
    $-- HOA

    What's special

    Charming mid-century residenceHardwood floorsDistinctive historic crown moldingBrick-paved tree-lined streetNewer stainless appliancesKitchen overlooks the backyard
    Rare Winter Park Opportunity | City-Approved 4,338 SF Buildable Area | R-2 Zoning | Detached Guest House Just a very short walk to Park Avenue, with restaurants, cafés, wine bars and boutiques within steps in virtually every direction, 950 S. Kentucky Avenue offers an exceptional combination of location, land, flexibility and future potential. Set on a 7,875-square-foot R-2 lot overlooking little Lake Midget and Park, the property allows for 4,338 square feet of buildable area, as approved by the City of Winter Park. The existing property is a charming mid-century residence on a brick-paved, tree-lined street. The block is distinguished by a mix of mature homes and beautiful new custom residences, including several striking modern homes that complement the neighborhood’s established character. The existing 2,155-square-foot home offers four bedrooms and three baths, including a detached one-bedroom, one-bath guest house with cabinetry already in place to complete a kitchenette. The detached guest house adds an unusual degree of versatility, whether used for guests, extended family, a private office or potential rental income. The current home can be enjoyed with some updating and improvements, allowing a new owner to take the time needed to create their ultimate vision. It features hardwood floors and distinctive historic crown molding salvaged from a Winter Park renovation. The kitchen overlooks the backyard and features a granite island and newer stainless appliances. A side entry from the tandem two-car carport leads into a practical mudroom with a tucked-away laundry closet. The spacious yard offers room for gardens, recreation, outdoor living and potentially a future pool. Recent improvements include a new roof in 2024, updated A/C in 2018, newer appliances and a transferable termite bond. Natural gas is available on-site. The location is truly special. Park Avenue and Central Park are a quick stroll away, while favorites including Croissant Gourmet, Ravenous Pig, Sushi Saint, Fiddler’s Green and Winter Park Playhouse are all within an easy walk. Rollins College, the Saturday Farmers Market, Hannibal Square and the many shops and restaurants of downtown Winter Park are also nearby. Families will also appreciate access to highly regarded Winter Park schools, including Audubon Park School (K–8) and Winter Park High School. Whether you choose to update and enjoy the existing home, use the guest house for additional flexibility or income, or ultimately create a new custom residence, 950 S. Kentucky Avenue offers a wonderful opportunity to live in the heart of Winter Park.
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    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Gwen Flynn 772-473-6084,

    COLDWELL BANKER REALTY 407-647-1211

    Source: Stellar MLS,MLS#: O6432779MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 3
      Rooms
      • Room types: Breakfast Room Separate, Florida Room, Utility Room
      Primary bedroom
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: First
      Bedroom 2
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      Bedroom 3
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      Primary bathroom
      • Features: Ceiling Fan(s), Shower No Tub, Window/Skylight in Bath
      • Level: First
      Bathroom 2
      • Features: Tub With Shower, Window/Skylight in Bath
      • Level: First
      Dinette
      • Features: Ceiling Fan(s)
      • Level: First
      Dining room
      • Level: First
      Florida room
      • Level: First
      Kitchen
      • Features: Breakfast Bar, Granite Counters
      • Level: First
      Living room
      • Features: Ceiling Fan(s)
      • Level: First
      Heating
      • Central, Electric, Heat Pump
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
      • Laundry: Electric Dryer Hookup, Inside, Laundry Closet, Washer Hookup
      Features
      • Ceiling Fan(s), Crown Molding, Dry Bar, Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters
      • Flooring: Tile, Hardwood
      • Doors: French Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 2,215
      • Total interior livable area: 2,155 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Covered, Driveway, On Street, Parking Pad
      • Carport spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Front Porch, Patio, Side Porch
      • Exterior features: Awning(s), Private Entrance, Private Mailbox, Private Yard, Sidewalk
      • Fencing: Chain Link
      • Has view: Yes
      • View description: Park/Greenbelt, Water, Lake
      • Has water view: Yes
      • Water view: Water,Lake
      • Body of water: LAKE MIDGET
      Lot
      • Size: 7,890 Square Feet
      • Dimensions: 75 x 105
      • Features: City Lot, Sidewalk
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Additional structures: Guest House
      • Parcel number: 122229255604050
      • Zoning: R-2
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cottage
      • Property subtype: Single Family Residence
      Materials
      • Block, Metal Siding
      • Foundation: Block, Crawlspace
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1941

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, Natural Gas Available, Public, Sewer Connected, Street Lights, Underground Utilities, Water Connected

      Community & HOA

      Community
      • Features: Park, Sidewalks
      • Security: Touchless Entry
      • Pet fee: $0 monthly
      • Subdivision: FAIRBANKS PARK
      HOA
      • Has HOA: No
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $371/sqft
      • Tax assessed value: $436,790
      • Annual tax amount: $6,939
      • Date on market: 8/13/2026
      • Cumulative days on market: 2 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Brick

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/13/2026Listed for sale$799,000+1663.8%$371/sqft
        Source: Stellar MLS #O6432779 Report a problem
        5/4/2025Listing removed$3,000$1/sqft
        Source: Zillow Rentals Report a problem
        4/23/2025Listed for rent$3,000+50%$1/sqft
        Source: Zillow Rentals Report a problem
        3/24/2021Listing removed--
        Source: Owner Report a problem
        9/28/2020Sold$45,300-69%$21/sqft
        Source: Public Record Report a problem
        4/14/2019Listing removed$2,000$1/sqft
        Source: Owner Report a problem
        4/9/2019Listed for rent$2,000$1/sqft
        Source: Owner Report a problem
        9/20/2011Sold$146,000+2.3%$68/sqft
        Source: Public Record Report a problem
        6/15/2011Sold$142,700+46.4%$66/sqft
        Source: Public Record Report a problem
        4/6/1998Sold$97,500$45/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$6,514 +6.8%$384,000 +10%
        2023$6,099 +24.4%$349,091 +10%
        2022$4,903 +2%$317,355 +4.2%
        2021$4,805 +10.6%$304,657 +21.3%
        2020$4,345 +4.9%$251,065 +10%
        2019$4,143 +3.4%$228,241 +10%
        2018$4,005 $207,492 -20.6%
        2017$4,005 +8%$261,260 +16.7%
        2016$3,708 +12.7%$223,779 +4.7%
        2015$3,289 +28.8%$213,677 +43.9%
        2014$2,554 +13.1%$148,458 +15.2%
        2013$2,258 -0.2%$128,836 +0.6%
        2012$2,262 -6.5%$128,044 -6.1%
        2011$2,418 -6.3%$136,379 -9.2%
        2010$2,579 $150,133 -19.4%
        2009-- $186,255 -11.6%
        2008$3,452 -6.9%$210,660 -7.5%
        2007$3,708 -8.6%$227,786 +0.4%
        2006$4,058 +4.7%$226,881 +8.1%
        2005$3,876 +22.8%$209,800 +21.3%
        2004$3,156 +44.4%$172,896 +39.6%
        2003$2,186 +16.9%$123,859 +16.8%
        2002$1,870 +6.3%$106,045 +7.7%
        2001$1,759 +2.9%$98,433 +3.8%
        2000$1,709 $94,819
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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: 32789

        Getting around

        86 / 100
        Very Walkable
        36 / 100
        Some Transit
        74 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Audubon Park K8
        • Middle: Glenridge Middle
        • High: Winter Park High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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