Neighborhood · Winter Park, Florida
Winter Park Village
Walkable luxury in the heart of Winter Park
3
Homes for sale
$1,150,000
Median list price
$512
Avg price / sqft
37
Median days on market
Winter Park Village puts you in the center of one of Orlando's most established communities, where dining, shopping, and lake life sit within an easy stroll of home. The area's character comes from surrounding pockets like Lake Killarney, the brick-street charm of Hannibal Square, and the settled residential feel of Winter Park Pines and Kenilworth. Downtown Orlando is about 24 minutes away and Orlando International Airport roughly 35, so you're connected without living in the noise.
The market here is tight and priced for the address. Only 3 homes are active right now, with a median list price of $1,150,000 and homes moving at around $512 per square foot. Over the past year just 5 homes sold at a median of $1,000,000, with sellers collecting about 94% of asking — a sign that well-priced Winter Park homes for sale still trade at strong values but leave room for a negotiated deal.
Winter Park Village is a community in Winter Park, Florida.
Quick facts
$589,000 – $1.6M price range
2,469 sqft median home
5 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Village
$1,150,000$1,175,000
1404 BORDER DRIVE, WINTER PARK
4 bd · 4 ba · 2,469 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
≈ $6,738/mo
$1,150,000 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 in the Orlando area, close to dining, shopping, and lakes like Lake Killarney. Homes are assigned to Dommerich Elementary, Maitland Middle, and Winter Park High, and downtown Orlando is only about 24 minutes away. If you want an established, connected neighborhood, it delivers.
Is Winter Park Village expensive?+
Yes — it sits at Winter Park's higher end, with a median list price of $1,150,000 and homes trading around $512 per square foot. Two of the three current active listings are priced above $1 million. It's a premium address, reflected in both the pricing and the walkable location.
What do homes cost in Winter Park Village?+
Active listings currently range from $589,000 to $1,599,000, with a median list price of $1,150,000 on a median home size of about 2,469 square feet. Over the past year, 5 homes sold at a median of $1,000,000. Compared to nearby Kenilworth, this is squarely in the luxury tier.
How is the market in Winter Park Village?+
Inventory is thin, with just 3 homes active and 5 sales in the past 12 months. Homes take a median of 37 days to sell, and sellers are getting about 94% of their asking price. That mix means motivated buyers still have room to negotiate on well-priced properties.
What about HOA fees and property taxes?+
Property taxes run a median of about $5,626 per year here. HOA data isn't consistently reported for this neighborhood, so fees vary by property — many homes in surrounding areas like Winter Park Pines carry little or no HOA. Always confirm the specifics on any home you're considering.
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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