Neighborhood · Winter Park, Florida
Downtown Winter Park
Walkable luxury on Central Florida's most storied avenue
7
Homes for sale
$1,849,900
Median list price
$784
Avg price / sqft
23
Median days on market
Downtown Winter Park is the kind of place where you can walk from a morning coffee to a gallery opening without moving your car. Anchored by the brick streets and cobblestones that define this corner of Winter Park, it gathers distinct pockets like Hannibal Square, Lake Killarney, and Kenilworth into one genuinely pedestrian-friendly core. It sits about 20 minutes from Downtown Orlando and roughly 41 minutes from Orlando International Airport, so you get a village pace without giving up big-city access.
For buyers, this is a tightly held, upper-end market. There are just 7 active listings right now with a median list price of $1,849,900, which tells you two things: inventory is scarce and the price of entry is high. If you want to be inside this walkable core, plan to move decisively when the right home comes up, and lean on comparable pockets like Winter Park Pines if you're weighing value against location.
Downtown Winter Park is a community in Winter Park, Florida.
Quick facts
$475,000 – $3.5M price range
2,143 sqft median home
$1,039/mo median HOA
$4,100/mo median rent
19 sold in 12 months
Drive times
On the market now
Homes for sale in Downtown Winter Park
$2,350,000
140 E MORSE BOULEVARD UNIT J, WINTER PARK
3 bd · 3 ba · 2,143 sqft
$475,000
644 N KNOWLES AVENUE UNIT 3, WINTER PARK
1 bd · 1 ba · 767 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
$2,070,000$2,095,000
147 S INTERLACHEN AVENUE UNIT 202, WINTER PARK
3 bd · 4.5 ba · 3,272 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
≈ $12,533/mo
$1,849,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$1,039/mo
Median HOA
From current listings inside the boundary
$4,100/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.
People who close here
Our Winter Park experts
Straight answers
Downtown Winter Park FAQs
Is Downtown Winter Park a good place to live?+
It's one of the most walkable neighborhoods in the region, with distinct pockets like Hannibal Square and Lake Killarney feeding into Winter Park High and Audubon Park School. You're about 20 minutes from Downtown Orlando and 41 minutes from the airport, so it balances a village feel with real connectivity. For buyers who want to trade the car for their feet, it's hard to beat.
Is Downtown Winter Park expensive?+
Yes — it's a premium market. The current median list price is $1,849,900, which places it well above most of the broader Orlando area. Buyers looking for more value while staying close by often compare it to Winter Park Pines.
What do homes cost in Downtown Winter Park?+
Right now there are 7 active listings with a median list price of $1,849,900. Because inventory is so limited, pricing can swing based on which specific homes are available at any given moment. It's worth tracking Winter Park homes for sale closely to catch the right listing early.
How is the market in Downtown Winter Park?+
It's a low-inventory, high-demand market — just 7 homes are active today. That scarcity means well-positioned buyers should be ready to act quickly rather than wait for a large selection. Neighboring areas like Kenilworth can offer additional options nearby.
What about HOA fees and property taxes?+
Specific HOA and property tax figures for the current active listings aren't available in the data, and they vary by pocket and property type here. Since this is an established, mostly non-gated part of Winter Park, your agent should pull exact HOA and tax numbers on any home you're considering before you write an offer.
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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