Homes for sale in
Winter Park, Florida
Brick streets, lakefront living just north of Orlando
348
Homes for sale
$627,000
Median list price
$425
Avg price / sqft
34
Median days on market
Winter Park has a distinct rhythm: oak-canopied brick streets, a chain of lakes, and a walkable core around Park Avenue and Hannibal Square that feels more like a village than a suburb of Orange County. Neighborhoods run the gamut here, from the historic bungalows of Orwin Manor to the lakeside lots around Lake Killarney and the mid-century homes of Winter Park Pines. It's the kind of place where you can bike to a coffee shop and still be zoned to well-regarded schools like Winter Park High and Audubon Park School.
For buyers, the market is layered. There are 348 active listings with a median list price of $627,000, but the range stretches from $85,000 condos to nearly $9 million lakefront estates — and 123 of those homes are priced above $1M. Homes sit a median of 34 days, so it moves at a reasonable pace, and there's real depth in the single-family homes segment alongside a healthy pool of townhomes & condos for entry buyers.
Winter Park is in Orange County, Florida.
Within a 30-minute drive
Quick facts
$85,000 – $8.9M price range
1,821 sqft median home
$2,400/mo median rent
Leans seller right now
Fresh on the market
Newest homes in Winter Park
View all 348 homes →
$1,250,000
1600 ALABAMA DRIVE UNIT 402, WINTER PARK
2 bd · 2 ba · 1,574 sqft
$470,000$480,000
2041 JEWELL AVENUE, WINTER PARK
3 bd · 1 ba · 1,508 sqft
$594,500
2010 SUMMERFIELD ROAD, WINTER PARK
3 bd · 2 ba · 1,889 sqft
$229,000
7454 WYNNEWOOD SQUARE UNIT 188, WINTER PARK
3 bd · 2.5 ba · 1,151 sqft
$1,360,000
420 OHIO STREET, WINTER PARK
5 bd · 5.5 ba · 3,735 sqft
$285,000
2372 SUN VALLEY CIRCLE UNIT 2372, WINTER PARK
2 bd · 2 ba · 1,495 sqft
$142,500
283 LEWFIELD CIRCLE UNIT 283, WINTER PARK
1 bd · 1 ba · 678 sqft
$148,000
1000 S SEMORAN BOULEVARD UNIT 408, WINTER PARK
1 bd · 1 ba · 776 sqft
$450,000
1564 LAWNDALE CIRCLE, WINTER PARK
4 bd · 2.5 ba · 1,980 sqft
$770,000
730 W SWOOPE AVENUE, WINTER PARK
5 bd · 3 ba · 2,132 sqft
$2,350,000
140 E MORSE BOULEVARD UNIT J, WINTER PARK
3 bd · 3 ba · 2,143 sqft
$1,350,000
1881 LAKE SPIER DRIVE, WINTER PARK
3 bd · 2 ba · 1,750 sqft
250 of 348 active listings shown
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Property features
The numbers that matter
The Winter Park market
Leans seller
4.9 months of inventory
Demand still outpaces supply, but buyers have a little more room.
Winter Park vs Orange County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 1.5% yr/yr
Homes on the market
▼ 10.5% yr/yr
Homes sold per month
Live Stellar MLS data — listings and closed sales in Winter Park, FL. Rolling medians smooth single-month swings in thin markets.
Where to look
Winter Park neighborhoods
Lake Killarney
34 homes · $473K median
Winter Park Pines
14 homes · $589K median
Hannibal Square
11 homes · $849K median
Kenilworth
10 homes · $1.2M median
Eastbrook
9 homes · $400K median
Orwin Manor
8 homes · $840K median
Downtown Winter Park
7 homes · $1.8M median
Waterfall Cove
7 homes · $135K median
Hidden Oaks
7 homes · $180K median
Cedarwood Village
7 homes · $255K median
The Stratford
6 homes · $154K median
Winter Woods
6 homes · $242K median
Lawndale
6 homes · $1.3M median
Garden Lake Estates
5 homes · $430K median
Maitland Shores
5 homes · $5.6M median
Colonies
5 homes · $159K median
Mead Garden
4 homes · $483K median
Parkview Village
4 homes · $167K median
Show all 213 Winter Park neighborhoods A–ZHide the full neighborhood list+
Neighborhood boundaries by edgeAI — listings matched to the actual polygon, not agent-entered subdivision names.
For the school run
School zones with homes for sale
Homes matched to official attendance boundaries — always verify zoning with the district.
Beyond the listings
Living in Winter Park
Walkable, lake-woven core
The area around Park Avenue and Hannibal Square pairs a genuine downtown with a chain of connected lakes, so waterfront and walkability aren't mutually exclusive.
Pool homes are plentiful
With 122 active listings featuring a pool, the private-backyard-oasis lifestyle is one of the easier things to find in this market.
A true luxury tier
123 of the 348 active listings are priced above $1M, including waterfront estates that reach nearly $9 million.
Range for every budget
Listings start around $85,000 and run to $8.95M, with condos and townhomes giving first-time buyers a real entry point.
New construction is available
There are 46 new-construction listings active, a meaningful count in an established, built-out community.
Population
29,929
Median age
44.2
Median income
$98,076
Median home value
$676,800
What people here are into
Hobbies & Interests
Top 7% 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.
Hobbies & Interests
Top 9% 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.
Food & Drink
Top 9% 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 9% 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 10% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Relationships
Top 11% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
On the calendar
Near Winter Park
Jul
11
Sat
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
11
Sat
Cue The Comedy
The weekly Saturday night comedy show in the heart of the Milk District in Orlando, Florida, promises a night of laughter and fun. Featuring nationally recognized and hou…
Jul
11
Sat
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
Jul
11
Sat
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
11
Sat
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
11
Sat
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
What it really costs
Owning here
Owning the median Winter Park home
≈ $4,314/mo
$627,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
3%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$2,400/mo
Median rent
89 homes for rent right now
People who close here
Our Winter Park experts
Krystina Allen
Real Estate Agent
1 closed here in 12 mo
Donna Layton
Real Estate Agent
1 closed here in 12 mo
Straight answers
Winter Park real estate FAQs
Is Winter Park a good place to live?+
It's one of the most established, walkable communities in metro Orlando, built around a chain of lakes and a genuine downtown. Neighborhoods like Kenilworth and Orwin Manor offer character, and homes are zoned to schools including Winter Park High and Audubon Park School. The blend of lake access, mature tree canopy, and a real village core is what keeps demand steady.
Is Winter Park expensive?+
It sits above the regional average — the median list price is $627,000 and the average price per square foot is $425. That said, the range is wide, from $85,000 up to $8.95M, so what you pay depends heavily on whether you're after a condo or a waterfront home.
What do homes cost in Winter Park?+
The median list price is $627,000, with a median home size of 1,821 square feet at about $425 per square foot. The luxury tier is substantial: 123 of the 348 active listings are priced above $1M, while townhomes & condos offer more affordable options at the lower end.
How is the Winter Park housing market right now?+
There are 348 active listings and homes are selling at a median of 34 days on market, which points to a steady, balanced pace rather than a frenzy. The mix skews heavily toward single-family residences (232), with 89 condos and 25 townhomes rounding out the choices. Buyers watching for value should keep an eye on just reduced listings.
What about HOA fees and property taxes?+
The median HOA runs about $387/month, though that's driven largely by condo and townhome communities — many single-family homes carry no HOA at all. Median property tax is around $4,954/year, and median rent sits at $2,400/month if you're weighing renting against buying.
Keep exploring
Nearby areas
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. Market statistics are computed from listing and sold data and change as the market moves.
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