206 N HIGHLAND AVENUE, WINTER GARDEN, FL, 34787
Active20 days on marketListed Sep 29, 2026MLS #O6444632
About this home
206 N HIGHLAND AVENUE
Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,880
Sqft
0.24 ac
Lot size
1
Garage
1925
Year built
One
Levels
$559
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.
$6,391 /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
$6,391/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.
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
+69.6%
$/sqft vs Winter Garden actives
$559 vs $259
Days on market
20 vs 61 typical
Where $559/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)
219 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 110% 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 206 N 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 · Aug ’26$555,000
227 W BAY STREET · same community
3 bd · 2 ba · 1,338 sqft · $415/sqft · 0 DOM
Sold · Sep ’26$1,260,000
217 W BAY STREET · same community
5 bd · 4 ba · 2,800 sqft · $450/sqft · 91 DOM
Sold · Jul ’26$455,000
837 GRANDE REGAL POINT
3 bd · 2 ba · 1,874 sqft · $243/sqft · 27 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
Leila Sabat
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 206 N HIGHLAND AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 206 N HIGHLAND AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Leila's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
206 N HIGHLAND AVENUE FAQs
What would the monthly payment be for 206 N HIGHLAND AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,391/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 206 N HIGHLAND AVENUE?+
The most recent tax bill on record (2025) was $2,054. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 206 N HIGHLAND AVENUE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Garden?+
At $1,050,000, this home is listed about 77% above the Winter Garden median of $592,495. The market section on this page shows how the area is trending.
Which schools are assigned to 206 N HIGHLAND AVENUE?+
Summerlake Elementary (elementary), Hamlin Middle (middle), Horizon High School (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$1,050,000 runs 110% above the WINTER GARDEN 34787 median.
02Strong assigned schools
Summerlake Elementary, Hamlin Middle, Horizon High School — Summerlake Elementary rates 5 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $1,100,000, now $1,050,000 — a $50K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of HOMEVEST REALTY · Erica Diaz. MLS #O6444632.
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 206 N 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 Leila to ping you on any price or status change →