950skentuckyavenuewinterparkfl32789

4 Beds

3 Full baths

2,155SqFt

Active

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.

Property Details
Price $799,000
Bedrooms 4
Full Baths 3
Half Baths 0
Property Style Cottage
Lot Size 75 x 105
Lot Size Area 7890
Lot Size Area Units Square Feet
Acres 0.18
Property Type Residential
Sub type SingleFamilyResidence
MLS Sub type Single Family Residence
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
Exterior Features Awning(s), French Doors, Private Entrance, Private Mailbox, Private Yard, Sidewalk
Year Built 1941
Subdivision FAIRBANKS PARK
View Park/Greenbelt, Water
Roof Shingle
Waterfront LAKE MIDGET
Heating Central, Electric, Heat Pump
Foundation Block, Crawlspace
Lot Description City Lot, Sidewalk
Laundry Features Electric Dryer Hookup, Inside, Laundry Closet, Washer Hookup
Parking Description Covered, Driveway, On Street, Parking Pad
Geographic Data
Directions From I-4 take Fairbanks Ave exit #87. Head east on W. Fairbanks Ave. (SR-426 E). In 1 mile turn right on Ward Ave. Continue 900 ft. on S Kentucky Ave. Home is on the right - 950 S Kentucky Ave. From Park Ave. Winter Park, turn right on W Fairbanks Ave/426. In 0.3 miles turn left on S. Denning Dr. In 500 ft. turn right on S Kentucky Ave. The home will be on the left - 950 S Kentucky Ave.
County Orange
Latitude 28.591418
Longitude -81.361814
Market Area 32789 - Winter Park
Address Information
Address 950 S KENTUCKY AVENUE, WINTER PARK, FL 32789
Postal Code 32789
City WINTER PARK
State FL
Country United States
Listing Information
Listing Office COLDWELL BANKER REALTY
Listing Agent Gwen Flynn
Special listing conditions None
Ownership Fee Simple
Terms Cash, Conventional
School Information
Elementary School Audubon Park K8
Middle School Glenridge Middle
High School Winter Park High
MLS Information
Days on market 0
MLS Status Active
Listing Date Aug 13, 2026
Listing Last Modified Aug 13, 2026
Tax ID 122229255604050
Tax Year 2025
Tax Annual Amount 6939
MLS Area 32789 - Winter Park
MLS # O6432779

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