Neighborhood · Winter Park, Florida
Downtown Winter Park
Walkable luxury where Park Avenue meets real neighborhoods
10
Homes for sale
$1,219,750
Median list price
$744
Avg price / sqft
60
Median days on market
Downtown Winter Park is the kind of place where you can walk from a brick-lined residential street to a sidewalk cafe in a few minutes. Between the shops and galleries of the central district and tucked-away pockets like Hannibal Square and Orwin Manor, this is one of the most pedestrian-friendly addresses in the Orlando area — and it's only about 20 minutes to downtown Orlando. The character runs from historic bungalows near Lake Killarney to new builds, with Winter Park homes for sale spanning a wide range of price and style.
For a buyer today, this is a tight, high-end market. There are just 10 active listings with a median list price of $1,219,750, and five of those are priced above $1 million. Homes here take their time — the median is 60 days on market — and over the last year sellers collected about 94% of asking, so there's room to negotiate if you come prepared.
Downtown Winter Park is a community in Winter Park, Florida.
Quick facts
$650,000 – $6.2M price range
2,103 sqft median home
$982/mo median HOA
$6,000/mo median rent
16 sold in 12 months
Drive times
On the market now
Homes for sale in Downtown Winter Park
$745,000$774,000
640 N PARK AVENUE UNIT 3, WINTER PARK
2 bd · 1.5 ba · 897 sqft
$6,195,000$6,200,000
698 N NEW YORK AVENUE, WINTER PARK
5 bd · 5.5 ba · 5,096 sqft
$1,450,000
100 S VIRGINIA AVENUE UNIT 201, WINTER PARK
3 bd · 3 ba · 2,756 sqft
$699,000
250 CAROLINA AVENUE UNIT 202, WINTER PARK
3 bd · 2 ba · 1,450 sqft
$739,000
250 CAROLINA AVENUE UNIT 205, WINTER PARK
2 bd · 2 ba · 1,311 sqft
$3,695,000$3,895,000
125 S INTERLACHEN AVENUE UNIT 1, WINTER PARK
3 bd · 4 ba · 3,878 sqft
$2,995,000$3,150,000
125 S INTERLACHEN AVENUE UNIT 2, WINTER PARK
3 bd · 4 ba · 3,244 sqft
$1,775,000$1,849,900
101 S NEW YORK AVENUE UNIT 311, WINTER PARK
3 bd · 3.5 ba · 3,112 sqft
$650,000$710,000
300 CAROLINA AVENUE UNIT 402C, WINTER PARK
3 bd · 2 ba · 1,350 sqft
$989,500
269 E CANTON AVENUE UNIT 269, WINTER PARK
1 bd · 1.5 ba · 1,109 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
16
Sold, last 12 months
$713,525
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
27 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
▲ 0.8% 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
≈ $8,499/mo
$1,219,750 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$982/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.
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 communities in the Orlando area, with Park Avenue's shops and restaurants minutes from residential streets. Established pockets like Eastbrook and Orwin Manor give it real neighborhood texture, and the area is zoned to Winter Park High. Downtown Orlando is about 20 minutes away.
Is Downtown Winter Park expensive?+
Yes — it sits firmly in the luxury tier. The median list price is $1,219,750 and homes average $744 per square foot, with five of the ten current listings priced above $1 million. Entry points do exist, with active listings starting around $650,000.
What do homes cost in Downtown Winter Park?+
Active listings run from $650,000 to $6,195,000, with a median list price of $1,219,750 on a typical home of about 2,103 square feet. Over the last 12 months, 16 homes sold at a median price of $713,525, so what actually closes tends to land well below the top of the asking range.
How is the market right now?+
It's a slower, negotiable market with just 10 homes available and a median 60 days on market. Sellers took about 94% of their asking price over the past year across 16 sales, which gives a serious buyer real leverage. Inventory in nearby Lake Killarney and surrounding pockets stays limited, so well-priced homes still move.
What should I expect for HOA and property taxes?+
The median HOA runs about $982 per month, though that varies widely by building and community, and five of the current listings are in gated settings. Median property taxes come in around $10,557 per year, in line with the area's higher home values.
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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