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.
Sold for $1,005,000
$1,005,000
244 OSCEOLA COURT, WINTER PARK, FL 32789
4beds
1,837sqft
Single Family Residence
Built in 1940
5,550 Square Feet Lot
$1,006,300 Zestimate®
$547/sqft
$3,612 Estimated rent
Home value
$1,006,300
$926,000 - $1.10M
$3,612/mo
Zestimate® history
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List your homeWhat's special
Renovated kitchenBreakfast barEn suite bathCozy family roomCircular paver patioDry barBuilt-in dressers
Zillow last checked:
Listing updated:
Listed by:
Maria Van Warner 407-256-8066,
FANNIE HILLMAN & ASSOCIATES 407-644-1234,
Andrea Parra Chopite, PA 407-515-0097,
FANNIE HILLMAN & ASSOCIATES
Bought with:
Karen Frier, 3426262
COLDWELL BANKER REALTY
Source: Stellar MLS,MLS#: O6372232
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Family Room, Living Room
Primary bedroom
- Description: Room6
- Features: Walk-In Closet(s)
- Level: First
- Area: 182 Square Feet
- Dimensions: 13x14
Bedroom 2
- Description: Room7
- Features: Built-in Closet
- Level: Second
- Area: 198.72 Square Feet
- Dimensions: 10.8x18.4
Bedroom 3
- Description: Room8
- Features: Built-in Closet
- Level: Second
- Area: 156.6 Square Feet
- Dimensions: 10.8x14.5
Bedroom 4
- Description: Room9
- Features: Built-in Closet
- Level: Second
- Area: 110 Square Feet
- Dimensions: 10x11
Dining room
- Description: Room3
- Level: First
- Area: 121 Square Feet
- Dimensions: 11x11
Family room
- Description: Room4
- Level: First
- Area: 95 Square Feet
- Dimensions: 9.5x10
Foyer
- Description: Room1
- Level: First
- Area: 72 Square Feet
- Dimensions: 6x12
Kitchen
- Description: Room5
- Level: First
- Area: 160 Square Feet
- Dimensions: 10x16
Living room
- Description: Room2
- Level: First
- Area: 150 Square Feet
- Dimensions: 12x12.5
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Gas Water Heater, Range, Refrigerator, Tankless Water Heater
- Laundry: Inside
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)
- Flooring: Tile, Hardwood
- Doors: French Doors
- Windows: Window Treatments
- Has fireplace: Yes
- Fireplace features: Gas, Living Room
Interior area
- Total structure area: 2,110
- Total interior livable area: 1,837 sqft
Property
Parking
- Parking features: Covered, Parking Pad
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Rear Porch, Screened
- Exterior features: Balcony, Courtyard, Rain Gutters, Sidewalk, Storage
- Fencing: Vinyl
- Waterfront features: Lake Privileges
- Body of water: LAKE OSCEOLA
Lot
- Size: 5,550 Square Feet
- Features: City Lot, Sidewalk, Street Dead-End
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 082230645602041
- Zoning: WP-R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Crawlspace
- Roof: Metal
Condition
- New construction: No
- Year built: 1940
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Water Connected
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: OSCEOLA COURT
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $547/sqft
- Tax assessed value: $683,809
- Annual tax amount: $6,454
- Date on market: 1/8/2026
- Cumulative days on market: 41 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 4/1/2026 | Sold | $1,005,000-16.3%$547/sqft |
Source:  Stellar MLS #O6372232 Report a problem | ||
| 2/18/2026 | Pending sale | $1,200,000$653/sqft |
Source: Stellar MLS #O6372232 Report a problem | ||
| 2/5/2026 | Price change | $1,200,000-5.9%$653/sqft |
Source: Stellar MLS #O6372232 Report a problem | ||
| 1/31/2026 | Price change | $1,275,000-1.8%$694/sqft |
Source: Stellar MLS #O6372232 Report a problem | ||
| 1/8/2026 | Listed for sale | $1,299,000+142.8%$707/sqft |
Source: Stellar MLS #O6372232 Report a problem | ||
| 12/13/2006 | Sold | $535,000+52.9%$291/sqft |
Source: Public Record Report a problem | ||
| 6/17/2003 | Sold | $350,000+44.6%$191/sqft |
Source: Public Record Report a problem | ||
| 10/16/2002 | Sold | $242,000$132/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $6,256 +4.3% | $436,262 +3.5% |
| 2023 | $5,999 +5% | $421,614 +3% |
| 2022 | $5,714 +1.2% | $409,334 +3% |
| 2021 | $5,648 -0.2% | $397,412 +1.4% |
| 2020 | $5,656 +0.8% | $391,925 +2.3% |
| 2019 | $5,613 +0.6% | $383,113 +1.9% |
| 2018 | $5,580 | $375,970 +1.6% |
| 2017 | $5,580 +0.9% | $370,226 +1.2% |
| 2016 | $5,528 +2.1% | $365,733 +2.1% |
| 2015 | $5,414 -2.4% | $358,156 +13.7% |
| 2014 | $5,550 +5.2% | $315,036 +4.6% |
| 2013 | $5,277 -2.4% | $301,080 -1.7% |
| 2012 | $5,408 -0.7% | $306,208 -0.3% |
| 2011 | $5,445 -0.4% | $307,130 -3.5% |
| 2010 | $5,465 | $318,154 -9.5% |
| 2009 | -- | $351,725 -18.5% |
| 2008 | $7,069 -7.4% | $431,388 -8% |
| 2007 | $7,636 +26.6% | $469,081 +39.1% |
| 2006 | $6,032 +3.1% | $337,242 +6.5% |
| 2005 | $5,851 +15.5% | $316,641 +14.2% |
| 2004 | $5,064 +64.7% | $277,382 +39.3% |
| 2003 | $3,074 +101.8% | $199,196 +19.8% |
| 2002 | $1,523 +0.7% | $166,282 +3.6% |
| 2001 | $1,512 +3% | $160,485 +2.2% |
| 2000 | $1,468 | $156,994 |
Find assessor info on the county website
Neighborhood: 32789
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Nearby schools
GreatSchools rating
- 10/10AUDUBON PARK SCHOOLGrades: PK-8Distance: 2.1 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Audubon Park K8
- Middle: Audubon Park K-8
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,006,300
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Estimated market value
$1,006,300
- Florida
- Orange County
- Winter Park
- 32789
- 244 OSCEOLA COURT
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