USAFLWinter ParkOsceola Court244 Osceola Ct

$1,200,000

Sold

4 months ago

244 Osceola Ct, Winter Park, FL

Name: 244 Osceola Ct, Sold in Winter Park - eXp Realty
Brand: FANNIE HILLMAN & ASSOCIATES
SKU: O6372232
Price: 1200000 USD

House

MLS® O6372232

Buyer represented by an agent of COLDWELL BANKER REALTY

4 Bed

3 Bath

1837 sqft

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 1837 sqft

Garage

Taxes $6,454

Lot Size

Approx. Age 1940

Avg. Price Per Sqft $653

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. Motivated Seller!! Call today to schedule your private showing.

MLS® NumberO6372232

Laundry LevelEnsuite

Central VacNo

FireplaceNo

Acreage

Exterior

Garage

Approx. Age1940

Basement

DrivewayCovered, Parking Pad

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

Feb 18, 2026End Date

$1,005,000Sold Price

Sold

Jan 8, 2026List Date

$1,200,000List Price

Commute

Commute

Starting Address

Destination Address

Similar Listings

Comparable Properties

Explore eXp Find an Agent Join eXp Investor Relations Company Careers Home Guides

eXp Life Zoocasa SUCCESS®SUCCESS® Lending eXp Revenos eXp Commercial eXp Luxury eXp Land and Ranch Accessibility

Terms and Conditions Privacy Rights Request Privacy Policy Cookie Policy Brand Guidelines Help Sitemap

2219 Rimland Drive, Suite 301, Bellingham, Washington, 98226

1 833-303-0610

[email protected]

eXp REALTY

DMCA Notice

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply

Fair Housing and Reasonable Accommodations

MLS Compliance Statements

Karen Richards - Designated Managing Broker, Broker Operations - TX

Texas Real Estate Commission information about brokerage services

Texas Real Estate Commission Consumer Protection Notice

eXp Realty® is committed to adhering to the guidelines of The New York State Fair Housing Regulations.The Fair Housing Notice →

*Standardized Operating Procedure for Purchasers of Real Estate Pursuant to Real Property Law 442-H.Learn More →

eXp Realty of California, Inc. | CA DRE# 01878277 | Deborah Penny - Designated Broker

eXp Realty of Southern California, Inc. | CA DRE#01325837 | Jason Crawford – Designated Broker

eXp Realty of Greater Los Angeles, Inc. | CA DRE# 01240990 | Mike Mendibles - Designated Broker

eXp Realty of Northern California, Inc. | CA DRE# 01951343 | Ryan Rosas - Designated Broker