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Jamie Deihl
REALTOR®
(719) 468-9744

244 Osceola Court, Winter Park, FL 32789

$1,200,000

34 Total Photos [Click to View All]

Property Description

Under contract-accepting backup offers. 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.

244 Osceola Court | MLS# O6372232

This single family home located at 244 Osceola Court, Winter Park, FL 32789 is currently listed for sale with an asking price of $1,200,000. This property was built in 1940 and has 4 bedrooms and 2 full and 1 partial baths with 1837 sq. ft. Osceola Court is located in the OSCEOLA COURT subdivision. Search OSCEOLA COURT real estate on jamiedeihl.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Heating: Central
Lot Size: 0.13 Acres
Roof Type: Metal
Stories: 2.0
Taxes: $6,454
Year Built: 1940
Square Feet: 1,837

Amenities

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
Balcony
Courtyard
French Doors
Rain Gutters
Sidewalk
Storage

Feature Descriptions

Additional Rooms: Attic, Family Room, Formal Living Room Separate
Appliances: Dishwasher, Disposal, Gas Water Heater, Range, Refrigerator, Tankless Water Heater
Body of Water: LAKE OSCEOLA
Community Features: Street Lights
Days on Site: 61
Directions: From Downtown Park Ave. Go East on Osceola then make a left on Osceola Ct. Second house on the right.
Exterior: Wood Siding
Fencing: Vinyl
Fireplace: Gas, Living Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile, Wood
Foundation: Crawlspace
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: City Limits, Sidewalk, Street Dead-End, Paved
Lot Dimensions: 0.13
Ownership: Fee Simple
Parking: Covered, Parking Pad
Parking Notes: Covered, Parking Pad
Patio/Porch: Patio, Rear Porch, Screened
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: ShowingTime
Special Sale Provisions: None
Special View Info: Water
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access: Lake - Chain of Lakes
Water Access Y/N: Yes
Zoning: WP-R-1AA

Room Sizes

Foyer: 6x12
Living Room: 12x12.5
Dining Room: 11x11
Family Room: 9.5x10
Kitchen: 10x16
Primary Bedroom: 13x14
Bedroom 2: 10.8x18.4
Bedroom 3: 10.8x14.5
Bedroom 4: 10x11

Local Schools

High School: Winter Park High
Middle School: Audubon Park K-8
Elementary School: Audubon Park K8

Listed By / Shown By

Listed By

Agency Name: FANNIE HILLMAN & ASSOCIATES
Agency Contact: 407-644-1234

Shown By

Agent Name: Jamie Deihl
Agent Phone: (719) 468-9744
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 6,674.41 per month $5,786.58 Principal & Interest $537.83 Property Tax $350.00 Homeowner's Insurance

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