Neighborhood · Winter Park, Florida
Winter Park Village
Walkable luxury at the center of Winter Park
3
Homes for sale
$1,599,000
Median list price
$572
Avg price / sqft
37
Median days on market
Winter Park Village puts you steps from shops, restaurants and open-air gathering spots at the heart of one of Orlando's most established communities. The surrounding neighborhoods each have their own texture — the lakefront calm around Lake Killarney, the mid-century streets of Winter Park Pines, and the historic energy of Hannibal Square. It's an easy 24-minute drive to downtown Orlando, and the whole area feeds into Winter Park High, one of the reasons families put down roots here.
For buyers, this is a small, high-end market that moves deliberately. There are just 3 active listings right now with a median list price of $1,599,000, and over the last year only 5 homes sold at a median of $1,000,000. Sellers are getting about 94% of asking and homes take a median 37 days to sell, so there's room to negotiate but not much inventory to choose from. If nothing fits, it's worth widening the search across Winter Park homes for sale or nearby Eastbrook.
Winter Park Village is a community in Winter Park, Florida.
Quick facts
$589,000 – $1.7M price range
2,715 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
$1,599,000$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
≈ $9,029/mo
$1,599,000 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 pockets of Winter Park, with shopping and dining right in the Village and assigned schools including Winter Park High. You're about 24 minutes from downtown Orlando and 35 from the airport, so it balances a settled neighborhood feel with easy access to the wider metro.
Is it expensive to buy here?+
Yes — this is a top-tier market with a median list price of $1,599,000 and an average of $572 per square foot. The current active listings range from $589,000 to $1,749,000, so most of the inventory sits well into seven figures.
What do homes cost in Winter Park Village?+
Over the last 12 months, 5 homes sold at a median price of $1,000,000, while active listings are asking a median of $1,599,000 for a typical home around 2,715 square feet. The gap reflects a small sample and the two new-construction listings currently on the market — for more options, look at the broader Winter Park homes for sale.
How is the market right now?+
It's a low-volume market with just 3 active listings and 5 sales in the past year. Homes take a median 37 days to sell and sellers are averaging about 94% of their asking price, so buyers have a little negotiating room even at the high end.
What about HOA fees and property taxes?+
Property taxes run a median of about $4,730 per year here. HOA data isn't available for the current listings, which is common in this part of Winter Park where many homes aren't tied to a mandatory association — always confirm on the specific property.
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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