144 Tildenville School Rd, Winter Garden, FL 34787
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.
Sale and tax history for 144 Tildenville School Rd
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6444651
Sep 25, 2026
Listed
$899,900
$609/sq ft
Stellar MLS as Distributed by MLS Grid #O6439913
Sep 8, 2026
Listed
$899,900
$609/sq ft
+44
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.
Public Records
Aug 21, 2017
Sold
$297,000
$201/sq ft
Public Records
Aug 31, 2004
Sold
$150,000
$101/sq ft
Public Records
Feb 4, 2000
Sold
$100,000
$68/sq ft
Public Records
Oct 4, 1996
Sold
$60,000
$41/sq ft
Public Records
Mar 1, 1978
Sold
$14,000
$9/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$3,547 (+5.9%)
2024
$3,350 (+11.1%)
2023
$3,015 (+4.0%)
2022
$2,899 (+1.8%)
2021
$2,846 (+5.2%)
2020
$2,707 (−2.5%)
2019
$2,777 (−32.7%)
$84,000 + $112,208
$196,208
2018
$4,125 (+74.3%)
$84,000 + $112,208
$196,208
2017
$2,366 (+3.9%)
$65,000 + $70,295
$135,295
2016
$2,278 (+2.6%)
$65,000 + $70,295
$135,295
2015
$2,220 (+17.9%)
2014
$1,883 (+3.4%)
2013
$1,820 (+0.3%)
2012
$1,815
Public record
Public record
Zoning
Beds
3
Baths
1
Stories
1
Lot width
—
Lot depth
—
Lot size
1.19 Acres
Year renovated
1978
Finished Sq. Ft.
1,478
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,478
Year built
1978
Style
Single Family Residential
County
Orange County
APN
272222000000082
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
A-1
Citrus Rural District
It is the intent and purpose of the agricultural districts to provide for agricultural and ranching uses, and not for subdivision and platting residential lots.
Permitted uses
Include but are not limited to:
Greenhouse / nursery
Livestock production
Fire house
Police station
Veterinary clinic
Agriculture-Cropland
Housing-Mobile home park
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.62% chance of being in a wildfire in next 30 years
8/10 Heat Factor
7 days above 108° expected this year, 24 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winter Garden, FL • 34787
Average low and high temperatures (°F)
68
49
74
54
80
60
84
65
89
72
91
75
92
76
91
76
88
74
82
68
78
60
72
55
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
99/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in Winter Garden. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.5 hrs
7.1 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 144 Tildenville School Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $475,000 and $1,040,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $475K to $1.0M.