Homes for sale in
Winter Park, Florida
Brick streets, chain-of-lakes living, minutes from downtown Orlando
326
Homes for sale
$575,000
Median list price
$419
Avg price / sqft
43
Median days on market
Winter Park sits just north of downtown Orlando with a walkable core of oak-lined streets, and a character that leans historic and unhurried. Neighborhoods run the full range here — from the cottages and townhomes around Hannibal Square to the lakefront estates near Lake Killarney and the established family blocks of Winter Park Pines. With downtown Orlando about 14 minutes out and MCO roughly 26, you get an in-town address without the in-town noise.
For buyers, this is a broad but pricey market: 317 homes are active with a median list of $599,000, and 108 of those listings sit above $1M, so the mix is real. Homes are selling at a measured 45-day median pace, and sellers are getting about 97% of asking — meaning well-priced listings move while overpriced ones sit. If your budget is tighter, it's worth watching the just reduced list and the condo end of the market, where entry prices start well below the median.
Winter Park is in Orange County, Florida.
Quick facts
$80,000 – $7.3M price range
1,749 sqft median home
$2,100/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Winter Park
View all 326 homes →
$3,150,000
125 S INTERLACHEN AVENUE UNIT 2, WINTER PARK
3 bd · 4 ba · 3,244 sqft
$285,000
283 SANDLEWOOD TRAIL UNIT 3, WINTER PARK
2 bd · 2.5 ba · 960 sqft
$245,000
1250 S DENNING DR Unit 233, WINTER PARK
2 bd · 2 ba · 913 sqft
$575,000
1071 ARAGON AVENUE, WINTER PARK
2 bd · 2.5 ba · 1,851 sqft
$625,000
1871 BRYAN AVENUE, WINTER PARK
3 bd · 2 ba · 1,232 sqft
$235,000
2712 TORTOISE CV, WINTER PARK
2 bd · 1 ba · 924 sqft
$2,699,000
1597 OAKHURST AVENUE, WINTER PARK
5 bd · 4.5 ba · 4,410 sqft
$419,900
1427 BROAD WING LANE, WINTER PARK
3 bd · 2.5 ba · 2,312 sqft
$340,000
1941 OGLESBY AVENUE, WINTER PARK
2 bd · 1 ba · 780 sqft
$899,000
1621 CHESTNUT AVENUE, WINTER PARK
3 bd · 2.5 ba · 2,022 sqft
$849,999
724 MONMOUTH WAY, WINTER PARK
5 bd · 3.5 ba · 2,832 sqft
$1,495,000
150 E READING WAY, WINTER PARK
3 bd · 2.5 ba · 2,080 sqft
250 of 326 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
3.8 months of inventory
Demand still outpaces supply, but buyers have a little more room.
1,009
Sold, last 12 months
$495,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
26 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
▼ 12.4% 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
26 homes · $473K median
Winter Park Pines
13 homes · $615K median
Eastbrook
10 homes · $399K median
Hannibal Square
10 homes · $1.1M median
Downtown Winter Park
9 homes · $1.8M median
Cedarwood Village
9 homes · $267K median
Orwin Manor
9 homes · $880K median
Lake Knowles Terrace
8 homes · $1.2M median
Kenilworth
8 homes · $1.9M median
Waterfall Cove
7 homes · $135K median
Hidden Oaks
7 homes · $185K median
Garden Lake Estates
6 homes · $450K median
Mead Garden
6 homes · $438K median
Charmont
6 homes · $2.1M median
Golfside
6 homes · $138K median
Golfside Villas
5 homes · $138K median
The Stratford
5 homes · $183K median
Lawndale
5 homes · $1.4M 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, historic core
Park Avenue's brick streets and the compact downtown give Winter Park a genuinely walkable center that most Orlando suburbs can't match.
Real waterfront inventory
With 22 [waterfront homes](/area/winter-park-fl/waterfront-homes) active, lakefront living around the chain of lakes is an actual option, not just a headline.
Pools are the norm
108 of the current listings include a pool, so a private [pool home](/area/winter-park-fl/homes-with-pool) is well within reach at many price points.
Strong school assignments
Homes here commonly feed Winter Park High along with Audubon Park School and several well-regarded middle schools.
Minutes from everything
Downtown Orlando is about 14 minutes, MCO and Universal roughly 26, and Walt Disney World about 38.
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
≈ $4,029/mo
$575,000 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
$2,100/mo
Median rent
86 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 addresses in Orange County, with a walkable historic downtown, mature tree canopy, and quick access to downtown Orlando in about 14 minutes. Homes commonly feed Winter Park High and Audubon Park School, which draws families alongside professionals who want an in-town lifestyle. The range of housing — from condos to lakefront estates — means it works for a lot of different buyers.
Is Winter Park expensive?+
It runs above the metro average: the median list price is $599,000 and $431 per square foot, and 108 of the 317 active listings are priced over $1M. That said, listings span from $80,000 up to $12.5M, so there's genuine range — you can browse by price to see where the entry points are, particularly among condos.
What do homes cost in Winter Park?+
The median list price is $599,000 and the median home is about 1,785 square feet at $431 per square foot. Over the last 12 months, 1,014 homes sold at a median of $494,000, so actual closing prices land somewhat below current asking. Single-family homes make up the bulk of inventory, with condos and townhomes filling in the lower end.
How is the Winter Park housing market right now?+
It's steady and balanced. The median time on market is 45 days and sellers are averaging 97% of their asking price, which points to a market where fairly priced homes sell but there's still room to negotiate. With 317 active listings and 38 of them new construction, buyers have real choice.
What about HOA fees and property taxes?+
The median HOA runs about $400/month, though that varies widely — condos and gated communities carry fees while many single-family blocks have none. Median property tax is around $4,849 per year, and the typical rent sits near $2,300/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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