Neighborhood · Winter Park, Florida
Winter Park Village
Walkable urban living beside Winter Park's best shopping
4
Homes for sale
$1,336,500
Median list price
$530
Avg price / sqft
45
Median days on market
Winter Park Village sits at the center of one of Central Florida's most polished enclaves, where tree-lined streets and a dense cluster of restaurants and shops put daily life within walking distance. The pace here is more urban than the surrounding single-family pockets, and it connects easily to neighboring areas like Lake Killarney and the historic feel of Hannibal Square. Families are drawn by the assigned schools — Winter Park High, Maitland Middle, and Dommerich Elementary — while downtown Orlando is roughly a 24-minute drive.
This is a tight, high-end market. With just 4 active listings and a median list price of $1,336,500, buyers are competing for a small pool of homes, two of which are new construction and three priced above $1M. Over the past year only 4 homes sold, at a median of $775,000, with sellers collecting about 94% of asking — so there's room to negotiate, but inventory moves and you'll want to be ready. Compare it against the broader Winter Park homes for sale to understand where your budget lands.
Winter Park Village is a community in Winter Park, Florida.
Quick facts
$620,000 – $1.7M price range
2,565 sqft median home
4 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Village
$1,699,900
2613 LAFAYETTE AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,661 sqft
$1,598,000
2430 CHANTILLY AVENUE, WINTER PARK
4 bd · 4 ba · 2,916 sqft
$620,000$660,000
1416 BORDER DRIVE, WINTER PARK
3 bd · 1 ba · 1,243 sqft
$1,075,000$1,100,000
1404 BORDER DRIVE, WINTER PARK
4 bd · 4 ba · 2,469 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
4
Sold, last 12 months
$775,000
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
164 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
▼ 36.4% 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
≈ $7,963/mo
$1,336,500 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.
People who close here
Our Winter Park experts
Straight answers
Winter Park Village FAQs
Is Winter Park Village a good place to live?+
It's one of the most walkable addresses in the area, with shopping, dining, and errands clustered close by and quick access to downtown Orlando in about 24 minutes. Families value the assigned schools — Winter Park High, Maitland Middle, and Dommerich Elementary. The character is more urban than nearby pockets like Eastbrook, which suits buyers who want lifestyle at their doorstep.
Is Winter Park Village expensive?+
Yes — it's a high-end market, with a median list price of $1,336,500 and three of the four active listings priced above $1M. Prices range from $620,000 to $1,699,900, so there's some spread, but the typical buyer here is shopping well above the broader Winter Park median. For context on the wider area, browse Winter Park homes for sale.
What do homes cost in Winter Park Village?+
Active listings run from $620,000 to $1,699,900 with a median list of $1,336,500, and homes trade at an average of $530 per square foot on a median size of about 2,565 square feet. Over the past 12 months the median sold price was $775,000, so recent closings came in below current asking prices. That gap reflects both the range of homes and a market where sellers get about 94% of list.
How is the market right now?+
It's thin and selective — just 4 active listings and 4 sales in the past year, with homes taking a median of 42.5 days to sell. Sellers are averaging 94% of asking, which signals some negotiating room without a buyer's-market free-for-all. Nearby Winter Park Pines can offer alternatives if the limited inventory here doesn't fit.
What about HOA fees and property taxes?+
Median property tax runs about $8,532 per year, in line with the area's higher price points. HOA data isn't available for the current listings, so confirm any dues directly on a specific property 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.
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