
144 TILDENVILLE SCHOOL ROAD, WINTER GARDEN, FL, 34787
Active13 days on marketListed Sep 8, 2026MLS #O6439913
About this home
144 TILDENVILLE SCHOOL ROAD
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.
Facts & features
The home at a glance
1.12 ac
Lot size
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$5,649 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$5,649/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Where it sits
Inside Winter Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
WINTER GARDEN 34787 — neighborhood snapshot
Population
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$585K → $611K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 82% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 144 TILDENVILLE SCHOOL ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$139,000
1222 WESTSIDE DRIVE
1 bd · 1 ba · 677 sqft · $205/sqft · 4 DOM
Sold · Nov ’25$150,001
143 W MORGAN STREET
2 bd · 1 ba · 780 sqft · $192/sqft · 26 DOM
Sold · Apr ’26$229,000
1166 WESTSIDE DRIVE
3 bd · 2 ba · 846 sqft · $271/sqft · 107 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Arlinda Gokyar
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 144 TILDENVILLE SCHOOL ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 144 TILDENVILLE SCHOOL ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Arlinda's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
144 TILDENVILLE SCHOOL ROAD FAQs
What would the monthly payment be for 144 TILDENVILLE SCHOOL ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,649/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 144 TILDENVILLE SCHOOL ROAD?+
The most recent tax bill on record (2025) was $3,547. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Garden?+
At $899,900, this home is listed about 57% above the Winter Garden median of $574,950. The market section on this page shows how the area is trending.
Which schools are assigned to 144 TILDENVILLE SCHOOL ROAD?+
Hamlin Elementary (elementary), Hamlin Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of COMPASS FLORIDA LLC · Matthew McKee. MLS #O6439913.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Winter Garden homes, in your inbox
Like 144 TILDENVILLE SCHOOL ROAD but not quite? A daily digest of every new listing in Winter Garden — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Arlinda to ping you on any price or status change →


