Neighborhood · Winter Park, Florida
Winter Park Hills
Established streets minutes from everything Winter Park
Winter Park Hills sits in one of Orange County's most established corners, surrounded by the mature oak canopy and lake-dotted geography that define Winter Park homes for sale. The neighborhood keeps company with well-known pockets like Lake Killarney, Winter Park Pines, and the walkable energy of Hannibal Square. Families are drawn here by a school assignment to Winter Park High, Maitland Middle, and Dommerich Elementary — a combination that anchors demand across the area.
For a buyer today, the reality is scarcity: there are currently no active listings on the market here. Over the past 12 months just 3 homes have sold, at a median price of $750,000, with sellers collecting about 92% of asking on average. That means when a home does come available, it pays to be ready to move — and to lean on Eastbrook and other nearby communities as backup options while you wait.
Winter Park Hills is a community in Winter Park, Florida.
Quick facts
3 sold in 12 months
On the market now
Homes for sale in Winter Park Hills
Nothing active right now.
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Every active listing inside the Winter Park Hills boundary
Open full map search →The numbers that matter
The Winter Park Hills market
3
Sold, last 12 months
$750,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
49 days
Median time to sell
Winter Park Hills vs Winter Park
Median sold price — 3-yr, 3-mo rolling
▼ 28.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Park Hills boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Park Hills is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
265
Median age
41
Median income
$117,237
Median home value
$517,600
Beyond the listings
Living in Winter Park Hills
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 Hills FAQs
Is Winter Park Hills a good place to live?+
It's an established Winter Park neighborhood assigned to Winter Park High, Maitland Middle, and Dommerich Elementary, which is a major reason families settle here. You're also close to lake-front areas like Lake Killarney and the walkable dining of Hannibal Square. The low turnover — just 3 sales in the past year — reflects owners who tend to stay.
Is Winter Park Hills expensive?+
It sits toward the upper end of the Winter Park market, with a median sold price of $750,000 over the last 12 months. That's consistent with the established, centrally located Winter Park homes for sale in this part of Orange County. Budget accordingly and be prepared to compete when inventory is this thin.
What do homes cost in Winter Park Hills?+
Recent sales point to a median around $750,000, based on the 3 homes that closed in the past year. There are no active listings right now, so pricing on the next available home will depend heavily on its size and condition. Comparing against nearby Winter Park Pines can help set expectations while you wait for a listing.
How is the market in Winter Park Hills?+
It's a low-supply, low-turnover market — currently zero active listings and only 3 sales in the last 12 months. Sellers averaged about 92% of asking price, which suggests measured, realistic negotiations rather than bidding frenzies. When a home hits the market here, being pre-approved and ready to act is essential.
What about HOA fees and property taxes?+
HOA and property tax figures aren't currently reported for this neighborhood in the MLS data, which is common for established Winter Park streets where HOA structures vary. We'd confirm those specifics on any individual property before you write an offer. Nearby communities like Eastbrook can offer a useful point of comparison on typical 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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