144 Tildenville School Road, Winter Garden, FL 34787
Local realty services provided by:CENTURY 21 Selling Paradise
Listed by: matthew mckee, alex mckee
Office: compass florida llc.
MLS#:O6439913
Source:MFRMLS
Price summary
- Price:$899,900
About this home
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....
Contact an agent
Home facts
- Listing ID #:O6439913
- Added:6 day(s) ago
- Updated:September 14, 2026 at 04:52 PM
Structure and exterior
- Lot area:1.12 Acres
- Levels:1 Story
Schools
- High school:West Orange High
- Middle school:Lakeview Middle
- Elementary school:Tildenville Elem
Utilities
- Water:Public
- Sewer:Septic Tank
Finances and disclosures
- Price:$899,900
- Tax amount:$3,547 (2025)
Features and amenities
- Amenities:BB/HS Internet Available
- Pool features:Public Pool
New listings near 144 Tildenville School Road
- Coming Soon
$350,000Coming Soon3 beds 3 baths1,625 sq. ft.1017 Priory Circle, WINTER GARDEN, FL 34787
MLS# O6438757Listed by: COMPASS FLORIDA LLC - New
$790,000Active5 beds 4 baths3,381 sq. ft.2242 Wintermere Pointe Drive, WINTER GARDEN, FL 34787
MLS# G5117774Listed by: NEXTHOME BEST RESULTS REAL ESTATE - New
$750,000Active6 beds 4 baths4,204 sq. ft.1523 Juniper Hammock Street, WINTER GARDEN, FL 34787
MLS# O6439797Listed by: INTEREALTY SERVICE - New
$1,149,000Active3 beds 4 baths2,040 sq. ft.72 N Park Avenue #8, WINTER GARDEN, FL 34787
MLS# O6441100Listed by: KELLER WILLIAMS CLASSIC - New
$2,500,000Active0.91 Acres880 W Plant Street, WINTER GARDEN, FL 34787
MLS# O6423134Listed by: REAL BROKER, LLC - New
$1,399,999Active5 beds 5 baths4,919 sq. ft.1720 Lake Roberts Landing Drive, WINTER GARDEN, FL 34787
MLS# O6436608Listed by: ACCORD REAL ESTATE SERVICES - New
$749,000Active4 beds 3 baths2,335 sq. ft.12021 Windstone Street, WINTER GARDEN, FL 34787
MLS# O6440149Listed by: CENTURY 21 CARIOTI - New
$230,000Active3 beds 3 baths1,216 sq. ft.988 Stucki Terrace, WINTER GARDEN, FL 34787
MLS# TB8539994Listed by: BEACHFRONT REALTY INC - New
$925,000Active5 beds 4 baths3,202 sq. ft.285 Crystal Wood Drive, WINTER GARDEN, FL 34787
MLS# O6440648Listed by: PULTE REALTY OF NORTH FLORIDA LLC - New
$724,999Active4 beds 4 baths2,958 sq. ft.16924 Tradewind Point, WINTER GARDEN, FL 34787
MLS# O6439183Listed by: REAL BROKER, LLC