244 OSCEOLA COURT, Winter Park, FL, 32789 | $1,200,000

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.

Features

  • Rooms: 9
  • Bedrooms: 4
  • Baths: 2 full / 1 half
  • Laundry: Inside
  • Year Built: 1940
  • Garage: Covered, Parking Pad
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 1,837
  • Acreage: 0.13
  • Est. Taxes: $6,454
  • Lot Desc: City Lot, Sidewalk, Street Dead-End
  • Elem. School: Audubon Park K8
  • Middle School: Audubon Park K-8
  • High School: Winter Park High
  • Appliances: Dishwasher, Disposal, Gas Water Heater, Range, Refrigerator, Tankless Water Heater
  • MLS#: O6372232
  • Days on Market: 41 days
  • Website: https://www.raveis.com
    /eprop/O6372232/244osceolacourt_winterpark_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 3/11/2026 11:32:06 PM)

William Raveis Family of Services

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Pam Famiglietti - The Pam Famiglietti TeamSales Associate

203.560.0753

Pam.Famiglietti@raveis.com

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Laurie BergerVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 12578

203.520.1925

Laurie.Berger@raveis.com

Our Executive Mortgage Banker:

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Our Insurance Division:

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244 OSCEOLA COURT, Winter Park, FL, 32789

$1,200,000

Pam Famiglietti - The Pam Famiglietti Team

Sales Associate

William Raveis Real Estate

Phone: 203.560.0753

Pam.Famiglietti@raveis.com

Laurie Berger

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.520.1925

Laurie.Berger@raveis.com

NMLS Mortgage Loan Originator ID 12578

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $960,000 $960,000 $960,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.000% 5.750%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.154% 6.121% 6.011%
Monthly Tax Payment $538 $538 $538
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $5,451 $5,756 $7,972
Total Monthly Payment $6,114 $6,419 $8,635

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.