$799,000
950 Kentucky Avenue
Winter Park, FL 32789
Listing updated: August 14, 2026 at 12:07 AM ET
Listing courtesy of Coldwell Banker Realty · Gwen Flynn · MLS #O6432779 · Active · 407-647-1211Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveAug 13, 2026
- Listed$799,000Aug 13, 2026
- Price increased$799,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Fairbanks Park
- County
- Orange
- Year built
- 1941
- Living area
- 2,155 sq ft
- Price/sq ft
- $371
- Building area
- 2,215 sq ft (Public Records)
- Lot size
- 7,890 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X* (12095C0255F)
- Annual taxes
- $6,940 (2025)
- Parcel #
- 12-22-29-2556-04-050
- Zoning
- R-2
- MLS #
- O6432779
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Tile, Wood
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), Crown Molding, Dry Bar, Eat-in Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters
- Laundry
- Electric Dryer Hookup, Inside, Laundry Closet, Washer Hookup
- Stories / Levels
- One
- Direction faces
- North
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central, Electric, Heat Pump
- Cooling
- Central Air
Parking
- Parking features
- Covered, Driveway, On Street, Parking Pad
- Carport
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- See city/county lease restrictions and short-term rental requirements.
Exterior & Construction
- Exterior features
- Awning(s), French Doors, Private Entrance, Private Mailbox, Private Yard, Sidewalk
- Construction materials
- Block, Metal Siding
- Roof
- Shingle
- Foundation
- Block, Crawlspace
- Water view
- Yes
- Road surface
- Brick
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Natural Gas Available, Public, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Primary Bathroom | First | |
| Living Room | First | |
| Dining Room | First | |
| Kitchen | First | |
| Florida Room | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Dinette | First | |
| Bathroom 2 | First |
Listing Details
- Listing date
- 2026-08-10
- On market date
- 2026-08-13
- Original list price
- $799,000
- Occupant type
- Vacant
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-08-13
- Tax legal description
- FAIRBANKS PARK O/46 LOT 5 & W 15 FT LOT4 BLK D
Flood risk
See FEMA for this zone’s designation and insurance requirements.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of August 14, 2026 at 12:07 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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