516 S HIGHLAND AVENUE, WINTER GARDEN, FL, 34787
Active120 days on marketListed May 25, 2026MLS #O6409675
About this home
516 S HIGHLAND AVENUE
**Back on the market! Buyer's contingency fell through- New Price to sell **Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to Newton Park to catch breathtaking sunsets over Lake Apopka. Hard to find, timeless charm and well maintained! Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind. Rare opportunity to own a one owner (since the 60's) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,716
Sqft
0.21 ac
Lot size
1955
Year built
One
Levels
$288
Per sqft
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.
$3,352 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$3,352/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−1.6%
$/sqft vs Winter Garden actives
$288 vs $260
Days on market
120 vs 42 typical
Where $288/sqft sits among the 400 Winter Garden actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
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)
221 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
Paper trail
This home's history
Reality check
What actually sold near 516 S HIGHLAND AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$370,000
13820 ORCHARD LEAF WAY
4 bd · 2.5 ba · 1,657 sqft · $223/sqft · 32 DOM
Sold · Feb ’26$347,000
314 WINTER NELLIS CIRCLE
3 bd · 2.5 ba · 1,601 sqft · $217/sqft · 11 DOM
Sold · Jan ’26$315,000
13879 GOLDEN RUSSET DRIVE
2 bd · 2.5 ba · 1,594 sqft · $198/sqft · 64 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
Chad Creech
President, Commercial and Development Services · CENTURY 21 Edge
Tours, negotiation, and every question about 516 S HIGHLAND AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 516 S HIGHLAND AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Chad's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
516 S HIGHLAND AVENUE FAQs
What would the monthly payment be for 516 S HIGHLAND AVENUE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,352/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 516 S HIGHLAND AVENUE?+
The most recent tax bill on record (2025) was $709. 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 $495,000, this home is listed about 14% below the Winter Garden median of $574,950. The market section on this page shows how the area is trending.
Which schools are assigned to 516 S HIGHLAND AVENUE?+
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.
The brief
Four things that matter here
01Garden views
The garden view is part of what you're buying — views hold value independently of the structure.
02Time on market is leverage
120 days on market against a Winter Garden median of 42 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Hamlin Elementary, Hamlin Middle, West Orange High — Hamlin Elementary rates 5 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $500,000, now $495,000 — a $5K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of WINDSOR REALTY GROUP INC · Lisa Bennett. MLS #O6409675.
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 516 S HIGHLAND AVENUE 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 Chad to ping you on any price or status change →