Neighborhood · Winter Park, Florida
Winter Park Estates
Classic Winter Park living close to everything
5
Homes for sale
$519,900
Median list price
$300
Avg price / sqft
26
Median days on market
Winter Park Estates sits in the heart of one of Orange County's most established communities, with tree-lined streets and easy reach to nearby Lake Killarney and the shops and restaurants around Hannibal Square. Homes here feed into well-regarded schools like Winter Park High and Lakemont Elementary, and you're roughly 20 minutes from Downtown Orlando and about 32 minutes from Orlando International Airport. It's the kind of place where daily errands, dining, and commutes all stay short.
For buyers, the market here moves quickly and prices sit in an approachable range for Winter Park homes for sale. With just 4 active listings and a median list price of $489,950, inventory is tight and well-priced homes don't linger — the median time on market is only 11 days. If you like the character of nearby areas like Eastbrook or Kenilworth, it pays to be ready to move when the right home appears.
Winter Park Estates is a community in Winter Park, Florida.
Quick facts
$380,000 – $575K price range
1,745 sqft median home
$4,000/mo median rent
11 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Park Estates
$519,900
731 BONGART ROAD, WINTER PARK
4 bd · 3 ba · 1,842 sqft
$429,900
2818 AMBERGATE ROAD, WINTER PARK
3 bd · 2 ba · 1,398 sqft
$380,000
2626 AMBERGATE ROAD, WINTER PARK
3 bd · 1 ba · 1,143 sqft
$525,000$550,000
2641 CARVELL COURT, WINTER PARK
4 bd · 2 ba · 2,126 sqft
$575,000
2627 AMBERGATE ROAD, WINTER PARK
4 bd · 3 ba · 1,745 sqft
Every active listing inside the Winter Park Estates boundary
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Browse Winter Park Estates
By feature — on the live map
Where the market lives
The numbers that matter
The Winter Park Estates market
11
Sold, last 12 months
$399,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
4 days
Median time to sell
Winter Park Estates vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 8.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Park Estates boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Park Estates 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 Estates home
≈ $3,399/mo
$519,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$4,000/mo
Median rent
Homes for rent inside the boundary
Population
1,032
Median age
39
Median income
$62,880
Median home value
$398,841
Beyond the listings
Living in Winter Park Estates
Food & Drink
Top 3% 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.
Lifestyles
Top 4% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Hobbies & Interests
Top 4% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Food & Drink
Top 4% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Hobbies & Interests
Top 5% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Active
Top 5% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
People who close here
Our Winter Park experts
Straight answers
Winter Park Estates FAQs
Is Winter Park Estates a good place to live?+
It's a well-located, established neighborhood close to Downtown Orlando (about 20 minutes) and the dining and shops near Hannibal Square. Assigned schools include Winter Park High, Maitland Middle, and Lakemont Elementary, and the area sits near lakes like Lake Killarney. It suits buyers who want a central Winter Park address without the largest price tags.
Is Winter Park Estates expensive?+
It's more approachable than much of Winter Park, with a median list price of $489,950 and active listings ranging from $380,000 to $575,000. There are currently no listings above $1M here. At an average of $307 per square foot, it's a solid value for the location.
What do homes cost in Winter Park Estates?+
The median list price is $489,950, while the median sold price over the past 12 months was $399,000. Homes run about $307 per square foot with a median size around 1,572 square feet. Two of the current active listings include a pool.
How is the real estate market here?+
It's a quick, competitive market — homes sell in a median of 11 days and sellers average 96% of their asking price. With just 4 active listings and 11 sales in the past year, inventory is limited, so serious buyers should be ready to act. The character here compares well to nearby Eastbrook.
What about HOA fees and property taxes?+
There's no reported HOA fee data for this neighborhood, so most homes here carry little or no HOA cost. The median property tax runs about $5,344 per year. For renters, the median rent in the area is around $3,400 per month.
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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