244 OSCEOLA CT Winter Park, FL 32789 Open Sat 2PM-4PM

UPDATED: 01/09/2026 06:30 PM ON MARKET: 1 days on market

$1,299,000

4 Beds3 Baths1,837 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 1,837 sqft

Price per Sqft $707

Subdivision Osceola Court

MLS Listing ID O6372232

Bedrooms 4

Full Baths 2

Half Baths 1

HOA Y/N No

Year Built 1940

Annual Tax Amount $6,454

Lot Size 5,662 Sqft

Acres 0.13

Property Sub-Type Single Family Residence

Source Stellar MLS

Location

State FL

County Orange

Community Osceola Court

Area 32789 - Winter Park

Zoning WP-R-1AA

Rooms

Other Rooms Attic,Family Room,Formal Living Room Separate

Interior

Interior Features Built-in Features,Crown Molding,High Ceilings,Kitchen/Family Room Combo,Living Room/Dining Room Combo,Primary Bedroom Main Floor,Solid Surface Counters,Solid Wood Cabinets,Split Bedroom,Stone Counters,Thermostat,Walk-In Closet(s),Window Treatments

Heating Central

Cooling Central Air

Flooring Tile,Wood

Fireplaces Type Gas,Living Room

Furnishings Negotiable

Fireplace true

Appliance Dishwasher,Disposal,Gas Water Heater,Range,Refrigerator,Tankless Water Heater

Laundry Inside

Exterior

Exterior Feature Balcony,Courtyard,French Doors,Rain Gutters,Sidewalk,Storage

Parking Features Covered,Parking Pad

Fence Vinyl

Community Features Street Lights

Utilities Available BB/HS Internet Available,Cable Available,Electricity Connected,Natural Gas Connected,Public,Sewer Connected,Water Connected

Water Access Yes

Water Access Desc Lake - Chain of Lakes

Roof Type Metal

Porch Patio,Rear Porch,Screened

Garage false

Private Pool No

Building

Lot Description City Limits,Sidewalk,Street Dead-End,Paved

Entry Level Two

Foundation Crawlspace

Lot Size Range 0 to less than 1/4

Sewer Public Sewer

Water Public

Structure Type Wood Siding

New Construction false

Schools

Elementary Schools Audubon Park K8

Middle Schools Audubon Park K-8

High Schools Winter Park High

Others

Senior Community No

Ownership Fee Simple

Acceptable Financing Cash,Conventional

Listing Terms Cash,Conventional

Special Listing Condition None

Property Description

Set in one of Winter Park's most sought-after locations, this 1940 home delivers something that's hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic build without the restrictions of a historic designation, giving the next owner freedom to update, expand, or personalize as they choose. Inside, you're welcomed by a proper foyer with original hardwood floors (currently painted white and able to be refinished) and crown molding throughout. A thoughtfully used desk nook sits beside the staircase, making great use of the space. To the left, the formal living room features a true masonry, natural gas fireplace and flows into a bright dining room that connects to a cozy family room—an enclosed former porch with French doors opening to the screened porch beyond. The renovated kitchen is stunning, featuring Carrara marble countertops, stainless steel appliances including a gas range, a pantry with custom storage, breakfast bar, and dry bar. The primary suite is located on the first floor and was formerly a garage conversion, now offering high ceilings, an en suite bath, built-in dressers, a walk-in closet with stackable washer and dryer, and French doors leading to a charming private courtyard. Upstairs are three additional bedrooms and a full bath with double sinks, subway tile and bead-board accents. The largest upstairs bedroom, once the original primary, includes a half bath, generous space for a seating area or desk, and French doors opening to a covered balcony. The fourth bedroom includes access to a full-size walk-in attic with ventilation and heat removal system—offering future expansion potential. Outdoor living is just as inviting, with a screened porch complete with natural gas grill hookup and sink, plus a fully fenced backyard featuring artificial turf, a circular paver patio, and an adorable shed designed to match the home. Major updates include a metal roof (2020), updated plumbing, electrical, windows, and doors (2012), tankless gas water heater, and whole-house generator. Additional perks include a transferable termite bond and covered parking pad. A rare opportunity to own a true Winter Park home where location, charm, and long-term potential come together. Call today to schedule your private showing!

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Last updated: 1/10/2026

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