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244 Osceola Court, Winter Park, FL 32789

Local realty services provided by:CENTURY 21 Affiliates
244 Osceola Court,Winter Park, FL 32789
$1,299,000
  • 4 Beds
  • 3 Baths
  • 1,837 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sat, Jan 10
    02:00 pm - 04:00 pm
  • Sun, Jan 11
    01:00 pm - 03:00 pm
Listed by: maria van warner, andrea parra chopite, pa
Office: fannie hillman & associates
MLS#:O6372232
Source:MFRMLS

Price summary

  • Price:$1,299,000
  • Price per sq. ft.:$615.64

About this home

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

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Home facts

  • Year built:1940
  • Listing ID #:O6372232
  • Added:1 day(s) ago
  • Updated:January 09, 2026 at 05:21 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Living area:1,837 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Central

Structure and exterior

  • Roof:Metal
  • Year built:1940
  • Building area:1,837 sq. ft.
  • Lot area:0.13 Acres

Schools

  • High school:Winter Park High
  • Middle school:Audubon Park K-8
  • Elementary school:Audubon Park K8

Utilities

  • Water:Public, Water Connected
  • Sewer:Public, Public Sewer, Sewer Connected

Finances and disclosures

  • Price:$1,299,000
  • Price per sq. ft.:$615.64
  • Tax amount:$6,454 (2025)
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