244 OSCEOLA COURT, Winter Park, FL 32789

• 4 beds |
• 3 baths |
• 1,837 sqft

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!

Listing Status:

Active

Date Added:

January 8, 2026

Data Last Updated:

February 9, 2026 at 7:22AM

Listing Office:

FANNIE HILLMAN & ASSOCIATES : 407-644-1234

Listing Agent:

Maria Van Warner : 407-256-8066

MLS ID:

O6372232

Interior

• General: Built-in FeaturesCrown MoldingHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s)Window Treatments
• Rooms: AtticFamily RoomFormal Living Room Separate
• Appliances: DishwasherDisposalGas Water HeaterRangeRefrigeratorTankless Water Heater
• Laundry: Inside
• Flooring: TileWood
• A/C: Central Air
• Heating: Central
• Fireplace: GasLiving RoomFireplace

Exterior

• General: BalconyCourtyardFrench DoorsRain GuttersSidewalkStorage
• Other Structures: Rear PorchScreenedPatio
• Parking: CoveredParking Pad

Construction

• Roofing: Metal
• General: Wood SidingTwoCrawlspace

Location

• Road/Access: Asphalt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: WP-R-1AAOSCEOLA COURT K/108 S 50 FT OF LOT 4 BLK B08-22-30-6456-02-041
• Fencing: Vinyl

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple