The real story of 144 Tildenville School Road is the land. Opportunities to own over an acre this close to Historic Downtown Winter Garden are becoming increasingly hard to find. Beneath a canopy of beautiful mature trees, this property offers something that cannot easily be recreated: space, privacy, character, and a location within Winter Garden’s golf cart district. The existing 3 bedroom home offers nearly 1,500 square feet of living space, but step into the backyard and you quickly understand what makes this property special. This is land meant to be enjoyed. Picture evenings beneath the trees with string lights glowing overhead, friends gathered around the custom built pizza oven, dinner being prepared in the summer kitchen, music playing, and plenty of room for everyone to spread out. For the next owner, the possibilities are just as compelling as the lifestyle already here. Enjoy the property as it is, create your own private retreat, expand upon the existing outdoor spaces, or simply appreciate the increasingly rare luxury of having over an acre of land near the heart of Winter Garden. And despite the privacy, you are still connected to the lifestyle that makes this area so desirable. Being within Winter Garden’s golf cart district means trips toward Historic Downtown Winter Garden can become part of the routine. Spend Saturday mornings at the Farmers Market, enjoy dinner along Plant Street, explore local shops and restaurants, or spend an afternoon on the West Orange Trail before heading home to your own piece of Winter Garden. Homes can be renovated. Kitchens can be changed. Finishes can be replaced. But you cannot manufacture another acre of mature, established land in a location like this. That is what makes 144 Tildenville School Road different. It is not simply a home for sale. It is an opportunity to own a substantial piece of Winter Garden, with the space to enjoy today and the possibilities to make it something entirely your own tomorrow.
Property Details
Price:
$899,900
MLS #:
O6444651
Status:
Active
Beds:
3
Baths:
1
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 25, 2026
Finished Sq Ft:
1,478
Total Sq Ft:
1,838
Lot Size:
48,787 sqft / 1.12 acres (approx)
Year Built:
1978
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Dryer, Refrigerator, Washer
Bathrooms
1 Full Bathroom
Cooling
Central Air
Flooring
Laminate, Tile
Heating
Central, Electric
Interior Features
Other, Solid Surface Counters, Thermostat
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Other
Construction Materials
Vinyl Siding
Direction Faces
East
Exterior Features
Awning(s), Lighting, Other, Outdoor Grill, Outdoor Kitchen, Private Entrance, Storage
Fencing
Wood
Lot Features
Landscaped, Oversized Lot, Private
Other Structures
Shed(s)
Patio And Porch Features
Covered, Rear Porch
Roof
Shingle
View
Trees/Woods
Financial
Tax Year
2025
Taxes
$3,547
Map
Community
- Address144 TILDENVILLE SCHOOL ROAD WINTER GARDEN FL
- SubdivisionN/A
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Oct 19, 2026
806
Single Family Listed
120
Avg DOM
278
Avg $ / SqFt
$744,002
Avg List Price
Property Summary
- Located in the N/A subdivision, 144 TILDENVILLE SCHOOL ROAD WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $899,900 and features 3 beds, 1 baths, and has approximately 1,478 square feet of living space, and was originally constructed in 1978. The current price per square foot is $609. The average price per square foot for Single Family listings in WINTER GARDEN is $278. The average listing price for Single Family in WINTER GARDEN is $744,002. To schedule a showing of MLS#o6444651 at 144 TILDENVILLE SCHOOL ROAD in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of COMPASS FLORIDA LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 144 TILDENVILLE SCHOOL ROAD
WINTER GARDEN, FL
