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$799,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,155 Sq. Ft.
  • Updated 1 day ago

Next open house:

Open House: 12:00 PM - 3:00 PM

Sunday 8/16 12:00 PM - 3:00 PM

950 S Kentucky Avenue,Winter Park, FL 32789

950 S Kentucky AvenueWinter ParkFL32789

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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.

Full Property Details for 950 S Kentucky Ave

General

  • Price: $799,000
  • Taxes: $6,939 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6432779
  • Updated: 8/14/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 10
  • Interior 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
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Electric Dryer Hookup, Inside, Laundry Closet, Washer Hookup

Additional Information

  • Security/Safety: Touchless Entry

Exterior

  • Exterior Features: Awning(s), French Doors, Private Entrance, Private Mailbox, Private Yard, Sidewalk
  • Deck/Patio: Covered, Front Porch, Patio, Side Porch
  • Porch/Patio/Deck: Covered, Front Porch, Patio, Side Porch

Parking

  • Carports: Yes
  • Carport: 2
  • Carport Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Covered, Driveway, On Street, Parking Pad

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: FAIRBANKS PARK
  • Driving 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.
  • Direction Faces: North

School Information

  • Elementary School: Audubon Park K8
  • Middle School: Glenridge Middle
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park
  • Community Features: Park, Sidewalks
  • Pet Restrictions: See city/county pet restrictions.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric, Heat Pump

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE MIDGET
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Natural Gas Available, Public, Sewer Connected, Street Lights, Underground Utilities, Water Connected

Structural Information

  • Architectural Info: Cottage
  • Architectural Style: Cottage
  • Exterior Const.: Block, Metal Siding
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,155
  • Sq. Ft. Source: Owner
  • Year Built: 1941

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: Park/Greenbelt, Water
  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,890
  • Lot Size: 7890
  • Lot Dimensions: 75 x 105
  • Frontage: Street Brick
  • Street/Road Desc.: Brick
  • Fencing (Description): Chain Link

Water Features

  • Water View: Yes
  • Water Front Name: LAKE MIDGET

Financial Considerations

  • Tax Amount: $6,939.71
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: FAIRBANKS PARK O/46 LOT 5 & W 15 FT LOT4 BLK D
  • Flood Zone Info: X*
  • APN: 122229255604050
  • Property ID: 122229255604050
  • Block/Lot/Section: D
Buyer's Brokerage Compensation: Contact Listing Agent
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— 950 S Kentucky Ave —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 950 S Kentucky Ave

School District:Orange County School District
NameGradesDistance
Audubon Park School
1500 Falcon Drive, Orlando, FL 32803
PK-81.9 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 950 S Kentucky Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/13/2026
Listed
$799,000
447.26%
MLS
9/08/2011
Sold
$146,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 950 S Kentucky Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,940
7%
$464,640
6%
2024
$6,514
7%
$436,790
2%
2023
$6,099
27%
$428,539
41%
2021
$4,805
-2%
$304,657
-4%
2022
$4,903
2%
$317,355
7%
2021
$4,805
16%
$297,401
4%
2019
$4,143
3%
$287,175
1%
2018
$4,005
8%
$285,493
9%
2017
$3,708
13%
$261,260
17%
2016
$3,289
4%
$223,779
44%
2015
$3,175
24%
$155,892
10%
2014
$2,554
13%
$141,720
10%
2013
$2,258
—
$128,836
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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950 S Kentucky Avenue, Winter Park, FL 32789 (MLS# O6432779) is a Single Family property with 4 bedrooms and 3 full bathrooms. 950 S Kentucky Avenue is currently listed for $799,000 and was received on August 13, 2026. This property is listed by Gwendolen Flynn from our Winter Park Office.Want to learn more about 950 S Kentucky Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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