Neighborhood · Winter Park, Florida
Winter Park Hills
Established Winter Park living, minutes from downtown Orlando
Winter Park Hills sits in one of Orange County's most established residential pockets, close to the tree-lined streets and lakes that define Winter Park. You're near neighborhoods with real identity — Lake Killarney, Winter Park Pines, and the historic Hannibal Square — with downtown Orlando about 16 minutes away and Orlando International Airport roughly 27. Assigned schools include Dommerich Elementary, Maitland Middle, and Winter Park High, a draw for families who want to stay put for years.
The market here is tight and quiet — there are currently no active listings, so this is a neighborhood you buy into by being ready when something opens up. Over the past 12 months just 3 homes changed hands, at a median sold price of $750,000, and sellers collected about 92% of asking on average. That combination of low inventory and few sales means buyers should line up financing early and lean on an agent who watches this specific pocket, along with nearby Eastbrook, for the moment inventory turns.
Winter Park Hills is a community in Winter Park, Florida.
Quick facts
3 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Hills
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
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 with easy access to the wider Winter Park area and downtown Orlando about 16 minutes away. Assigned schools include Dommerich Elementary, Maitland Middle, and Winter Park High, which is a major reason families settle in and stay. Low turnover — just 3 sales in a year — tells you residents are in no hurry to leave.
Is Winter Park Hills expensive?+
It sits at the higher end of the market, with a median sold price of $750,000 over the past 12 months. That reflects Winter Park's desirability and the neighborhood's proximity to lakes, schools, and downtown Orlando. Rentals here run around $4,495 per month at the median.
What do homes cost in Winter Park Hills?+
The median sold price over the last year was $750,000 across 3 recorded sales. There are no active listings at the moment, so pricing is best judged against recent sales and comparable nearby pockets like Winter Park Pines. Expect to move quickly and competitively when a home does list.
How is the market in Winter Park Hills?+
It's a low-inventory, low-volume market — currently zero active listings and only 3 sales in the past 12 months. Sellers held strong pricing power, averaging about 92% of asking. Buyers should get pre-approved and set up alerts so they're ready the moment something in or near Eastbrook and Winter Park Hills hits the market.
What about HOA fees and property taxes?+
Current HOA and property tax figures aren't available in the active data, largely because there are no listings on the market right now. Taxes in Orange County are assessed on value, so a home near the $750,000 median will carry a bill scaled to that. Your agent can pull exact figures on any specific property once one becomes available.
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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