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Active · Single Family

950 KENTUCKY AVENUE

WINTER PARK, FL 32789

Beds
4 beds
Baths
3 baths
Area
2,155 sqft
Single FamilyBuilt 19417,890 sqft lotCentral, Electric, Heat PumpCentral Air$371/sqft7 days on market

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.

RRENA ValiQRENA ValiQ is an estimated value, blended from public sale comps, neighbourhood trend and this listing’s own metrics. It is a reference, not a guaranteed or asking price. The final number moves on diligence, terms and timing.Estimate

Sample estimate — not an appraisal

$843k
+5.5% vs asking
$795k low$891k high

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
Estimated monthly payment$4,618/mo
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.

DateEventPriceChange
Aug 10, 2026Listed$799,000

NeighbourhoodSample data

Reference scores for WINTER PARK, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.

Walk Score
82/ 100
Very walkable
Transit Score
35/ 100
Some transit
Bike Score
69/ 100
Bikeable
Elementary school
Audubon Park K8
Assigned school from the MLS record
Middle school
Glenridge Middle
Assigned school from the MLS record
High school
Winter Park High
Assigned school from the MLS record

Location

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