Neighborhood · Winter Park, Florida
Winter Park Village
Walkable dining, lakeside living, minutes from downtown
4
Homes for sale
$1,349,500
Median list price
$540
Avg price / sqft
50
Median days on market
Winter Park Village sits at the center of one of Orlando's most established addresses, where a walkable core of shops and restaurants meets tree-lined streets and small, distinct pockets like Lake Killarney and the historic Hannibal Square. It's the kind of place where you can leave the car at home for dinner, then be in Winter Park Pines or Eastbrook minutes later — and still reach downtown Orlando in about 24 minutes when you need to. Families here are drawn to assigned schools like Winter Park High and Dommerich Elementary, and the overall feel is polished but genuinely lived-in.
For buyers, this is a tight, high-end market. There are just 4 active listings right now with a median list price of $1,349,500, ranging from $589,000 up to $1,749,000, and three of the four are asking $1M or more. Homes are moving deliberately — a median of 50 days on market — and over the past year the 5 sold homes closed at a median of $1,000,000 with sellers netting about 94% of asking. If you want in, expect to compete on quality more than volume, and browse the broader Winter Park homes for sale to widen your options.
Winter Park Village is a community in Winter Park, Florida.
Quick facts
$589,000 – $1.7M price range
2,592 sqft median home
5 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Village
$1,749,000
2525 LAFAYETTE AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,715 sqft
$589,000$595,000
1319 BESSMOR ROAD, WINTER PARK
3 bd · 2 ba · 1,126 sqft
$1,100,000$1,150,000
1404 BORDER DRIVE, WINTER PARK
4 bd · 4 ba · 2,469 sqft
$1,599,000$1,665,000
2430 CHANTILLY AVENUE, WINTER PARK
4 bd · 4 ba · 2,916 sqft
Every active listing inside the Winter Park Village boundary
Open full map search →Find your fit
Browse Winter Park Village
By feature — on the live map
Where the market lives
The numbers that matter
The Winter Park Village market
5
Sold, last 12 months
$1,000,000
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
245 days
Median time to sell
Winter Park Village vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 63.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Park Village boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Park Village is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winter Park Village home
≈ $7,752/mo
$1,349,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
263
Median age
41
Median income
$117,237
Median home value
$517,600
Beyond the listings
Living in Winter Park Village
Hobbies & Interests
Top 3% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Beliefs
Top 4% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Food & Drink
Top 4% in the U.S.Asian Food & Culture
Asian culture has a lot to offer, but the Asian cuisine tends to be the most frequently referenced. This population is talking about Asian dishes, holidays, and drinks.
Food & Drink
Top 5% in the U.S.Trendy Eats
Meals are a social experience, and these foodies take it to the next level. This population can't wait to snap a pic of their plate and share it before chowing down.
Food & Drink
Top 5% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Food & Drink
Top 6% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Straight answers
Winter Park Village FAQs
Is Winter Park Village a good place to live?+
It's one of the more walkable, established parts of Winter Park, with a dining-and-shopping core at its center and quiet residential pockets around it. Families value the assigned schools — Winter Park High, Maitland Middle and Dommerich Elementary — and the roughly 24-minute drive to downtown Orlando keeps it well connected. Nearby areas like Hannibal Square add historic texture to the neighborhood.
Is it expensive to buy here?+
Yes — this is a high-end market. The median list price is $1,349,500, and three of the four current listings are priced at $1M or more, with active homes running from $589,000 up to $1,749,000.
What do homes cost in Winter Park Village?+
Active listings average about $540 per square foot on a median home size of 2,592 sqft, and the current median list price is $1,349,500. Over the past 12 months, the 5 homes that sold closed at a median price of $1,000,000. Nearby Lake Killarney offers another point of comparison if you're weighing options.
How is the market right now?+
It's a small, deliberate market with just 4 active listings and a median 50 days on market. Sellers have been getting about 94% of their asking price on average, so there's some room to negotiate but not a lot of surplus inventory to choose from.
What about HOA fees and property taxes?+
Median property tax runs about $5,178 per year here. HOA data isn't consistently reported for this neighborhood, so fees vary by community — it's worth confirming on any specific home before you make an offer.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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 Park Village homes, in your inbox
A daily digest of new Winter Park listings — straight from the MLS. Unsubscribe anytime.