Additional Information
Additional Lease Restrictions
Buyers to verify lease restrictions with City of Winter Park.
Additional Parcels YN
false
Additional Rooms
Attic, Family Room, Formal Living Room Separate
Appliances
Dishwasher, Disposal, Gas Water Heater, Range, Refrigerator, Tankless Water Heater
Building Area Source
Public Records
Building Area Total Srch SqM
196.03
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
694.07
Community Features
Street Lights
Construction Materials
Wood Siding
Cumulative Days On Market
22
Elementary School
Audubon Park K8
Exterior Features
Balcony, Courtyard, French Doors, Rain Gutters, Sidewalk, Storage
Fireplace Features
Gas, Living Room
Foundation Details
Crawlspace
High School
Winter Park High
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
Internet Address Display YN
true
Internet Automated Valuation Display YN
true
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Living Area Source
Estimated
Living Area Units
Square Feet
Lot Features
City Limits, Sidewalk, Street Dead-End, Paved
Lot Size Square Meters
516
Middle Or Junior School
Audubon Park K-8
Modification Timestamp
2026-01-30T22:31:09.689Z
Parcel Number
08-22-30-6456-02-041
Patio And Porch Features
Patio, Rear Porch, Screened
Previous List Price
1299000
Price Change Timestamp
2026-01-30T22:30:23.000Z
Property Attached YN
false
Public Remarks
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!
RATIO Current Price By Calculated SqFt
694.07
Realtor Info
Sign, Termite Bond/Warranty
Showing Requirements
ShowingTime
Status Change Timestamp
2026-01-08T20:57:51.000Z
Tax Legal Description
OSCEOLA COURT K/108 S 50 FT OF LOT 4 BLK B
Total Acreage
0 to less than 1/4
Universal Property Id
US-12095-N-082230645602041-R-N
Unparsed Address
244 OSCEOLA CT
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected
Vegetation
Mature Landscaping, Trees/Landscaped
Water Access
Lake - Chain of Lakes
Water Body Name
LAKE OSCEOLA
