USAFLWinter ParkOsceola Court244 Osceola Ct

244 Osceola Ct, WINTER PARK, FL

Name: 244 Osceola Ct, For Sale in WINTER PARK - Zoocasa
Brand: fannie hillman & associates
SKU: O6372232
Price: 1299000 USD

House

For Sale

Listed price in listed location currency (USD).

$1,299,000

430

MLS® O6372232

Open House

Sun Jan 11, 6:00-8:00 PM UTC

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 1837 sqft

Garage No

Taxes $6,454

Days Active 1

Lot Size 0.13 acres

Approx. Age 1940

Avg. Price Per Sqft $707

MLS® Number O6372232

Property Address: 244 Osceola Ct, WINTER PARK, FL, 32789-4431

Average square foot calculated using Size range provided by listing agent.

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!

MLS® NumberO6372232

Laundry LevelInside

Central VacNo

FireplaceNo

Acreage0.13

Exterior

GarageNo

Approx. Age1940

Basement

DrivewayCovered, Parking Pad

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Similar Listings

Price History

-End Date

Not Sold YetSold Price

For Sale

Jan 8, 2026List Date

$1,299,000List Price

Commute

Commute

Starting Address

Destination Address

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