950 KENTUCKY AVENUE
WINTER PARK, FL 32789
About this home
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.
Facts & features
Interior
- Bedrooms
- 4
- Bathrooms
- 3
- Living area
- 2,155 sqft
- Heating
- Central, Electric, Heat Pump
- Cooling
- Central Air
- Flooring
- Tile, Wood
- Stories
- 1
- Features
- Ceiling Fans(s), Crown Molding, Dry Bar, Eat-in Kitchen, Living Room/Dining Room Combo, Open Floorplan…
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range…
Exterior & lot
- Lot size
- 7,890 sqft (0.18 ac)
- Roof
- Shingle
- Construction
- Block, Metal Siding
- Exterior
- Awning(s), French Doors, Private Entrance, Private Mailbox, Private Yard, Sidewalk
Parking
- Carport
- 2 spaces
Financial
- Annual tax
- $6,940 (2025)
- Price / sqft
- $371/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- Cable Available, Electricity Connected, Natural Gas Available, Public, Sewer Connected, Underground Utilities…
Property
- Property type
- Single Family
- Year built
- 1941
- Subdivision
- FAIRBANKS PARK
- County
- Orange
Assigned schools
- Elementary
- Audubon Park K8
- Middle
- Glenridge Middle
- High
- Winter Park High
Listing
- Status
- Active
- Days on market
- 3 days
- MLS #
- MFR802505305
- Source
- Stellar MLS
Listed by Gwen Flynn · COLDWELL BANKER REALTY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
Based on 19 comparable sales within 4 miles of WINTER PARK, FL, this home is priced under RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $4,040/mo
- Property tax
- $578/mo
- Home insurance
- $0/mo
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own bill; insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Aug 10, 2026 | Listed | $799,000 | — |
NeighbourhoodSample data
Reference scores for WINTER PARK, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Location
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