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.
Lot/land
$899,900
144 TILDENVILLE SCHOOL ROAD, WINTER GARDEN, FL 34787
--beds
0baths
1.12Acres
Unimproved Land
Built in ----
1.12 Acres Lot
$847,300 Zestimate®
$--/sqft
$-- HOA
What's special
- 13 days
- 643
- 94
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Matthew McKee 407-948-0658,
COMPASS FLORIDA LLC 407-203-9441,
Alex McKee 407-765-4488,
COMPASS FLORIDA LLC
Source: Stellar MLS,MLS#: O6439913
Originating MLS: Osceola

Facts & features
Interior
Bedrooms & bathrooms
- Bathrooms: 0
Video & virtual tour
Property
Features
- Fencing: Wood
Lot
- Size: 1.12 Acres
- Dimensions: 157 x 335
Details
- Parcel number: 222227000000082
- Zoning: A-1/CITRUS
- Special conditions: None
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: BB/HS Internet Available
Community & HOA
Community
- Pet fee: $0 monthly
HOA
- Has HOA: No
Location
- Region: Winter Garden
Financial & listing details
- Tax assessed value: $343,806
- Annual tax amount: $3,547
- Date on market: 9/8/2026
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Dirt, Gravel
Estimated market value
$847,300
$805,000 - $890,000
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/8/2026 | Listed for sale | $899,900+203% |
Source: | ||
| 8/21/2017 | Sold | $297,000+98% |
Source: Public Record Report a problem | ||
| 8/31/2004 | Sold | $150,000+150% |
Source: Public Record Report a problem | ||
| 10/4/1996 | Sold | $60,000 |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $3,350 +11.1% | $229,404 +6.2% |
| 2023 | $3,015 +4% | $215,926 +3% |
| 2022 | $2,899 +1.8% | $209,637 +3% |
| 2021 | $2,846 +1% | $203,531 +1.4% |
| 2020 | $2,819 +1.5% | $200,721 +2.3% |
| 2019 | $2,777 -32.7% | $196,208 -17.3% |
| 2018 | $4,125 | $237,321 +75.4% |
| 2017 | $4,125 +74.3% | $135,295 +1.1% |
| 2016 | $2,366 +3.8% | $133,779 +1.9% |
| 2015 | $2,279 +21% | $131,259 +40.5% |
| 2014 | $1,884 +3.5% | $93,431 +3.4% |
| 2013 | $1,820 +0.3% | $90,342 +1% |
| 2012 | $1,815 -3.2% | $89,425 -3.3% |
| 2011 | $1,875 -3% | $92,497 -6.5% |
| 2010 | $1,932 | $98,878 -14.3% |
| 2009 | -- | $115,334 -17.2% |
| 2008 | $2,516 -4.6% | $139,376 -7.4% |
| 2007 | $2,636 -0.1% | $150,562 +9.3% |
| 2006 | $2,639 +14.4% | $137,758 +18.5% |
| 2005 | $2,307 +96.9% | $116,253 +36% |
| 2004 | $1,172 +0.9% | $85,506 +1.7% |
| 2003 | $1,161 +3.1% | $84,057 +5.3% |
| 2002 | $1,126 -0.5% | $79,851 +4.6% |
| 2001 | $1,131 -13% | $76,306 +28.8% |
| 2000 | $1,301 | $59,227 |
Find assessor info on the county website
Monthly payment
Climate risks
Neighborhood: 34787
Nearby schools
Schools provided by the listing agent
- Elementary: Tildenville Elem
- Middle: Lakeview Middle
- High: West Orange High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.





