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244 Osceola Court, WINTER PARK, FL 32789
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244 Osceola Court
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Priced at Only: $1,299,000
For more Information Call:
Address: 244 Osceola Court, WINTER PARK, FL 32789
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  • MLS#: O6372232 ( Residential )
  • Street Address: 244 Osceola Court
  • Viewed: 3
  • Price: $1,299,000
  • Price sqft: $616
  • Waterfront: No
  • Year Built: 1940
  • Bldg sqft: 2110
  • Bedrooms: 4
  • Total Baths: 3
  • Full Baths: 2
  • 1/2 Baths: 1
  • Days On Market: 3
  • Additional Information
  • Geolocation: 28.5963 / -81.3441
  • County: ORANGE
  • City: WINTER PARK
  • Zipcode: 32789
  • Subdivision: Osceola Court
  • Elementary School: Audubon Park K
  • Middle School: Audubon Park K
  • High School: Winter Park
  • Provided by: FANNIE HILLMAN & ASSOCIATES
  • Contact: Maria Van Warner
  • 407-644-1234
  • mfrmls
  • DMCA Notice
  • Description
    Set in one of Winter Parks most sought after locations, this 1940 home delivers something thats 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, youre 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 rooman 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 systemoffering 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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  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
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Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Balcony, Courtyard, French Doors, Rain Gutters, Sidewalk, Storage
  • Fencing: Vinyl
  • Flooring: Tile, Wood
  • Living Area: 1837.00
  • Roof: Metal
Land Information
  • Lot Features: City Limits, Sidewalk, Street Dead-End, Paved
School Information
  • High School: Winter Park High
  • Middle School: Audubon Park K-8
  • School Elementary: Audubon Park K8
Garage and Parking
  • Garage Spaces: 0.00
  • Open Parking Spaces: 0.00
  • Parking Features: Covered, Parking Pad
Eco-Communities
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Dishwasher, Disposal, Gas Water Heater, Range, Refrigerator, Tankless Water Heater
  • Country: US
  • Furnished: Negotiable
  • 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
  • Legal Description: OSCEOLA COURT K/108 S 50 FT OF LOT 4 BLK B
  • Levels: Two
  • Area Major: 32789 - Winter Park
  • Occupant Type: Owner
  • Parcel Number: 08-22-30-6456-02-041
  • Zoning Code: WP-R-1AA
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Headshot for Associate Frank Filippelli
  1. Frank Filippelli, Broker,CDPE,CRS,REALTOR ®
  2. Southern Realty Ent. Inc.
  3. Mobile: 407.448.1042
  4. frank4074481042@gmail.com