Neighborhood · Winter Park, Florida
Winter Park Village
Walkable luxury minutes from Park Avenue
4
Homes for sale
$1,374,500
Median list price
$545
Avg price / sqft
49
Median days on market
Winter Park Village sits at the center of one of Central Florida's most established communities, where tree-lined streets and lakeside pockets meet a genuinely walkable core. You're a short stroll or drive from the shops and dining that define this part of Winter Park, with distinct nearby enclaves like Lake Killarney, Winter Park Pines, and the historic Hannibal Square each offering its own character. Downtown Orlando is about 24 minutes away, and MCO airport is roughly 35 — close enough for commuters, far enough to keep the pace calm.
For buyers today, this is a compact, high-end market: just 4 active listings with a median list price of $1,374,500, ranging from $589,000 up to $1,749,000. Homes trade at around $545 per square foot on a median size near 2,592 sqft, and sellers have been getting about 94% of asking. With only 5 homes sold in the past year at a $1,000,000 median and listings sitting a median 48.5 days, expect limited inventory and room to negotiate on well-priced offers.
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
$1,150,000$1,175,000
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
≈ $7,884/mo
$1,374,500 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 spots in the area, with dining and shopping close at hand and downtown Orlando about 24 minutes away. Families also value the assigned schools, which include Dommerich Elementary, Maitland Middle, and Winter Park High. Nearby enclaves like Winter Park Pines add options for buyers who want a quieter residential feel.
Is Winter Park Village expensive?+
Yes, this is a high-end market. The median list price is $1,374,500, with three of the four active listings priced above $1 million, and homes trade around $545 per square foot. Entry points do exist, though — the current range starts at $589,000.
What do homes cost in Winter Park Village?+
Active listings range from $589,000 to $1,749,000, with a median list price of $1,374,500 on homes around 2,592 square feet. Over the past 12 months, 5 homes sold at a median of $1,000,000, so recent sale prices have run below current asking levels.
How is the market right now?+
It's small and selective, with only 4 active listings and 5 sales in the past year. Homes sit a median of 48.5 days before going under contract, and sellers are getting about 94% of asking on average — which leaves informed buyers some negotiating room. Two of the active listings are new construction, and two include pools.
What about HOA fees and property taxes?+
Property taxes run a median of about $5,178 per year based on recent data. HOA figures aren't consistently reported for this pocket, so confirm any dues on a per-property basis. It's worth reviewing these numbers alongside listings across Winter Park to compare your true carrying costs.
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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