144 TILDENVILLE SCHOOL ROAD, Winter Garden, FL 34787

• 3 beds |
• 1 bath |
• 1,478 sqft

Property Description

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.

Listing Status:

Active

Date Added:

September 25, 2026

Data Last Updated:

September 28, 2026 at 3:21PM

Listing Office:

COMPASS FLORIDA LLC : 407-203-9441

Listing Agent:

Matthew McKee : 407-948-0658

Contact:

407-203-9441

MLS ID:

O6444651

Interior

• General: OtherSolid Surface CountersThermostat
• Appliances: DishwasherDryerRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: LaminateTile
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: Awning(s)LightingOtherOutdoor GrillOutdoor KitchenPrivate EntranceStorage
• Style: Other
• Other Structures: Shed(s)Rear PorchCovered

Construction

• Roofing: Shingle
• General: Vinyl SidingOneSlab

Location

• Road/Access: Dirt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: A-1W 157 FT OF N 330 FT OF E 510 FT OF NW1/4 OF NW1/4 OF SEC 22-22-2722-22-27-0000-00-082
• View: Trees/Woods
• Fencing: Wood

Utilities

• Utilities: BB/HS Internet Available
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple