Neighborhood · Winter Park, Florida
Downtown Winter Park
Walkable luxury at the heart of Winter Park
8
Homes for sale
$2,099,950
Median list price
$846
Avg price / sqft
17
Median days on market
Downtown Winter Park is where brick streets, mature oaks, and a cluster of galleries, cafes, and boutiques give the area its unmistakable character. This is a walk-everywhere kind of place, with distinctive pockets like Hannibal Square and lakeside living near Lake Killarney all within reach. Downtown Orlando is roughly 20 minutes away, so you get a genuine neighborhood feel without cutting yourself off from the wider metro.
For buyers, this is a top-of-market address and the numbers show it. There are just 8 active listings with a median list price of $2,099,950, though the range runs from $475,000 all the way to $3,895,000 — so entry points exist alongside the trophy homes. Homes here move quickly at a median of 17 days, and if you want more variety consider looking at nearby Winter Park Pines or Eastbrook as part of your broader Winter Park search.
Downtown Winter Park is a community in Winter Park, Florida.
Quick facts
$425,000 – $3.9M price range
2,628 sqft median home
$1,282/mo median HOA
$6,000/mo median rent
19 sold in 12 months
Drive times
On the market now
Homes for sale in Downtown Winter Park
$3,150,000
125 S INTERLACHEN AVENUE UNIT 2, WINTER PARK
3 bd · 4 ba · 3,244 sqft
$3,895,000
125 S INTERLACHEN AVENUE UNIT 1, WINTER PARK
3 bd · 4 ba · 3,878 sqft
$2,350,000
140 E MORSE BOULEVARD UNIT J, WINTER PARK
3 bd · 3 ba · 2,143 sqft
$3,500,000
649 N PARK AVENUE, WINTER PARK
3 bd · 4 ba · 3,180 sqft
$989,500
269 E CANTON AVENUE UNIT 269, WINTER PARK
1 bd · 1.5 ba · 1,109 sqft
$1,849,900
101 S NEW YORK AVENUE UNIT 311, WINTER PARK
3 bd · 3.5 ba · 3,112 sqft
$750,000
300 CAROLINA AVENUE UNIT 402C, WINTER PARK
3 bd · 2 ba · 1,350 sqft
$425,000$475,000
644 N KNOWLES AVENUE UNIT 3, WINTER PARK
1 bd · 1 ba · 767 sqft
Every active listing inside the Downtown Winter Park boundary
Open full map search →Find your fit
Browse Downtown Winter Park
By feature — on the live map
Where the market lives
The numbers that matter
The Downtown Winter Park market
19
Sold, last 12 months
$632,100
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
20 days
Median time to sell
Downtown Winter Park vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 41.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Downtown Winter Park boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Downtown Winter Park is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Downtown Winter Park home
≈ $14,168/mo
$2,099,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$1,282/mo
Median HOA
From current listings inside the boundary
$6,000/mo
Median rent
Homes for rent inside the boundary
Population
640
Median age
28
Median income
$69,124
Median home value
$587,230
Beyond the listings
Living in Downtown Winter Park
Hobbies & Interests
Top 2% 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.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Food & Drink
Top 4% 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.
Hobbies & Interests
Top 5% 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.
Appearance oriented
Top 6% in the U.S.Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Relationships
Top 7% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Straight answers
Downtown Winter Park FAQs
Is Downtown Winter Park a good place to live?+
It's one of the most established and walkable neighborhoods in the Orlando area, with brick streets, boutiques, and lakeside pockets like Lake Killarney close at hand. Families are typically assigned to Winter Park High and Audubon Park School, and Downtown Orlando is only about 20 minutes away. It combines a genuine neighborhood feel with quick access to the wider metro.
Is Downtown Winter Park expensive?+
Yes — it's a top-of-market address, with a median list price of $2,099,950 and five of the eight active listings priced above $1 million. That said, the range starts at $475,000, so there are more accessible entry points if you're patient and flexible on the type of home.
What do homes cost in Downtown Winter Park?+
Active listings run from $475,000 to $3,895,000, with the median around $2.1 million and an average of $854 per square foot on a median home size of 2,628 square feet. Over the last 12 months, 19 homes sold at a median price of $632,100, which reflects the mix of smaller condos and larger estates trading in the area.
How is the market in Downtown Winter Park right now?+
It moves quickly — the median days on market is just 17, and sellers are getting about 95% of their asking price on average. With only 8 active listings, inventory is tight, so serious buyers should be ready to act when the right home comes up; nearby Eastbrook can offer additional options.
What about HOA fees and property taxes here?+
The median HOA runs about $1,282 per month, reflecting the number of condos and gated communities in the area, and the median property tax is roughly $19,347 per year given the high price points. If you're renting instead, the median rent is around $6,000 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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