950 S KENTUCKY AVENUE Winter Park, FL $ 799,000
950 S KENTUCKY AVENUE
$ 799,000
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Open House 8/16 12pm - 3pm
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950 S KENTUCKY AVENUE

Winter Park, FL, 32789
$ 799,000
Bedrooms4 Baths3.0 Sq 2,155

Monthly Estimate*

$ 5,045

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Single Family Home for sale in Winter Park, FL

for $799,000 with 4 bedrooms and 3 full baths. This 2,155 square foot home was built in 1941 on a lot size of 0.18.

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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Open House

8/16/2026 12:00 PM - 3:00 PM
950 S KENTUCKY AVENUE Winter Park, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 799,000

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 6,939

Style

Cottage

Lot Size

0.18

Year Built

1941

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6432779

Features
General
Sewer Public Sewer
Heating Central Electric Heat Pump
Cooling Central Air
Utilities Cable Available Electricity Connected Natural Gas Available Public Sewer Connected Street Lights Underground Utilities Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Disposal Dryer Electric Water Heater Microwave Range Refrigerator Washer
Zoning R-2
Patio/Porch Features Covered Front Porch Patio Side Porch
Architectural Style Cottage
Security Features Touchless Entry
Construction Materials Block Metal Siding
Pets Allowed Yes
Year Built 1941
View Park/Greenbelt Water
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Park Sidewalks
County Orange
New Construction false
Property Type Residential
Subdivision Name FAIRBANKS PARK
Facing Direction North
Garage Y/N false
Other Structures Guest House
Total Rooms 10
Full Baths 3
Status Active
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.
High School Winter Park High
City WINTER PARK
Body of Water LAKE MIDGET
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 7890
Carport Spaces 2
Carport Y/N true
Listing Terms Cash Conventional
Elementary School Audubon Park K8
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 6939.71
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6432779
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 5
Legal Description FAIRBANKS PARK O/46 LOT 5 & W 15 FT LOT4 BLK D
Water View Lake
Minimum Lease 8-12 Months
Water Access Y/N false
Additional Rooms Breakfast Room Separate Florida Room Inside Utility
ILS Total SQFT 396
ILS Under Air SQFT 396
Water View Y/N true
Flood Zone Code X*
In Law Suite YN true
In Law Suite Description 1 Bathroom Detached (ADU) Private Entrance Studio
DockY/N false
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Interior
Interior Amenities 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
Furnished Y/N Unfurnished
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Electric Dryer Hookup Inside Laundry Closet Washer Hookup
Total Bedrooms 4
Total Baths 3
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Exterior
Exterior Amenities Awning(s) French Doors Private Entrance Private Mailbox Private Yard Sidewalk
Vegetation Mature Landscaping Trees/Landscaped
Fencing Chain Link
Parking Features Covered Driveway On Street Parking Pad
Lot Features City Lot Sidewalk
Water Source Public
Lot Size Area 7890
Foundation Details Block Crawlspace
Building Area Total 2215
Lot Dimensions 75 x 105
Lot Size Acres 0.18
Road Surface Type Brick
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Brick
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* Excluded Features
List By
Coldwell Banker Realty

Broker

gwendolen.flynn@floridamoves.com

Email

Affordability Calculator

$5,623
Per Month
90%
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Monthly Principal & Interest
$5,045
Monthly Property Taxes
$578
Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
8/13/2026$799,000 Listed Price

Map


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950 S KENTUCKY AVENUE, Winter Park, FL, 32789 is a Single Family Home for sale at $799,000 with 2,155 sqft and a lot size of 0.18. 950 S KENTUCKY AVENUE has 4 bedrooms, 3.0 baths, and was built in 1941. The property's zip code is 32789 which is in Winter Park, FL