Homes for sale in
Winter Park, Florida
Brick streets, chain of lakes, and real neighborhoods
340
Homes for sale
$599,000
Median list price
$431
Avg price / sqft
58
Median days on market
Winter Park sits just north of Orlando with a walkable core, a chain of lakes threading through town, and a mix of historic bungalows and modern builds. Neighborhoods run the gamut — the leafy streets of Orwin Manor, the in-town energy of Hannibal Square, the family-friendly Winter Park Pines, and the lakeside lots near Lake Killarney. It's an easy 14 minutes to downtown Orlando and 26 to MCO, so you get real character without giving up the commute.
The market here is broad and active: 357 homes are listed right now, from an $89,900 entry point up to nearly $7 million, with a median list price of $659,000. Sellers are getting about 97% of asking and homes move in a median of 38 days, so pricing is disciplined but not frantic. With 125 listings above $1M and a healthy run of single-family homes alongside condos and townhomes, buyers at most price points have room to shop.
Winter Park is in Orange County, Florida.
Quick facts
$89,900 – $7.0M price range
1,788 sqft median home
$2,125/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Winter Park
View all 340 homes →
$1,399,900
1737 INDIANA AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,984 sqft
$325,000
1462 SICILIANO POINT, WINTER PARK
3 bd · 2.5 ba · 1,628 sqft
$2,500,000
1760 OAKHURST AVENUE, WINTER PARK
5 bd · 4.5 ba · 3,700 sqft
$745,000$774,000
640 N PARK AVENUE UNIT 3, WINTER PARK
2 bd · 1.5 ba · 897 sqft
$1,150,000
1602 ALABAMA DRIVE UNIT 107, WINTER PARK
2 bd · 2 ba · 993 sqft
$350,000
310 GRANADA DRIVE, WINTER PARK
3 bd · 2 ba · 1,344 sqft
$255,000
1500 GAY ROAD UNIT 26-C, WINTER PARK
2 bd · 2 ba · 1,026 sqft
$379,900$395,000
3416 ARBUTUS LANE, WINTER PARK
4 bd · 3 ba · 1,421 sqft
$139,999
3032 ANTIQUE OAKS CIRCLE UNIT 145, WINTER PARK
1 bd · 1 ba · 749 sqft
$185,000
4882 TANGERINE AVENUE UNIT 4882, WINTER PARK
2 bd · 1.5 ba · 1,281 sqft
$491,000
1407 BROAD WING LANE, WINTER PARK
3 bd · 2.5 ba · 2,308 sqft
$575,000
112 BELL PLACE, WINTER PARK
3 bd · 2 ba · 2,253 sqft
250 of 340 active listings shown
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Most popular Winter Park searches
Popular searches
Property features
The numbers that matter
The Winter Park market
Leans seller
4.0 months of inventory
Demand still outpaces supply, but buyers have a little more room.
993
Sold, last 12 months
$495,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
25 days
Median time to sell
Winter Park vs Orange County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 8.3% yr/yr
Homes on the market
▼ 12.0% 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
25 homes · $460K median
Eastbrook
14 homes · $405K median
Orwin Manor
12 homes · $967K median
Hannibal Square
12 homes · $1.1M median
Winter Park Pines
10 homes · $665K median
Downtown Winter Park
10 homes · $1.2M median
Kenilworth
10 homes · $1.1M median
Cedarwood Village
8 homes · $259K median
Hidden Oaks
8 homes · $174K median
Golfside
7 homes · $138K median
Lake Knowles Terrace
6 homes · $1.6M median
Mead Garden
6 homes · $308K median
Winter Woods
6 homes · $507K median
Golfside Villas
5 homes · $138K median
Garden Lake Estates
5 homes · $430K median
Brookshire Heights
5 homes · $825K median
Colonies
5 homes · $150K median
Winter Park Estates
5 homes · $520K 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-laced core
Downtown Winter Park's brick streets and the surrounding chain of lakes give the area a distinct in-town character that's rare in the Orlando metro.
Wide price spectrum
Active listings run from $89,900 to nearly $7 million, with a $659,000 median that leaves room for both first buyers and luxury shoppers.
Strong seller conditions
Homes sell at about 97% of asking price in a median of 38 days, signaling steady demand across neighborhoods.
Pools and waterfront
Of the current inventory, 129 homes have a pool and 26 sit on the water, plus 25 gated options for buyers wanting more privacy.
Easy metro access
Downtown Orlando is roughly 14 minutes away and MCO airport about 26, with Universal and Disney within a 40-minute reach.
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.
What it really costs
Owning here
Owning the median Winter Park home
≈ $4,198/mo
$599,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
2%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$2,125/mo
Median rent
96 homes for rent right now
People who close here
Our Winter Park experts
Straight answers
Winter Park real estate FAQs
Is Winter Park a good place to live?+
Winter Park pairs a walkable downtown and a chain of lakes with quick access to the wider Orlando metro — about 14 minutes to downtown Orlando and 26 to the airport. Assigned schools most commonly include Winter Park High and Audubon Park School. Neighborhoods like Kenilworth and Orwin Manor give buyers established, tree-lined options close to the core.
Is Winter Park expensive?+
It runs above the metro average: the median list price is $659,000 and average price per square foot is about $440. That said, the range is wide — active listings start at $89,900 — and 125 of the current 357 listings are priced above $1 million, which pulls the top end up. You can browse by price to find where you fit.
What do homes cost in Winter Park?+
Median list price is $659,000 today, while the median sold price over the last 12 months was $497,000 across 998 closed sales. The typical home is around 1,861 square feet at roughly $440 per square foot. The housing mix leans single-family (242 active), with 82 condos and 29 townhomes also on the market.
How is the Winter Park market right now?+
It's steady and seller-favorable: homes are getting about 97% of asking and selling in a median of 38 days. With 357 active listings and 998 sales in the past year, there's real turnover and choice. Watching the just reduced listings can help you spot negotiable opportunities.
What about HOA fees and property taxes?+
The median HOA runs about $407 per month, though that varies widely — single-family homes often carry no HOA while condos and gated communities tend higher. Median annual property tax is around $5,201. Both depend heavily on the specific property and community you choose.
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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