Neighborhood · Winter Park, Florida
Hannibal Square
Historic walkability at the heart of Winter Park
10
Homes for sale
$1,124,000
Median list price
$566
Avg price / sqft
29
Median days on market
Hannibal Square sits at the west edge of downtown Winter Park, a district with real history and a genuine walk-to-everything rhythm — sidewalk cafés, galleries, and Park Avenue a short stroll away. This is a place where you can live in a restored bungalow or a modern build and still walk to dinner, which is rare in Orange County. Nearby Lake Killarney and established pockets like Kenilworth round out the area's character, and downtown Orlando is only about 18 minutes away.
For buyers, this is a small, tightly held market — just 10 active listings right now, half of them above $1M. Median list price is $1,124,000, but the sold data tells a more nuanced story: 19 homes closed in the past year at a median of $550,000, and sellers are averaging 96% of asking. Homes here move at a reasonable pace, with a median 29 days on market, so serious buyers should be ready to act on the right property. Compare it against neighboring Winter Park Pines or Eastbrook if you want more inventory to weigh.
Hannibal Square is a community in Winter Park, Florida.
Quick facts
$649,900 – $2.8M price range
2,594 sqft median home
$463/mo median HOA
$2,400/mo median rent
19 sold in 12 months
Drive times
On the market now
Homes for sale in Hannibal Square
$719,900
436 W SWOOPE AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,602 sqft
$2,800,000
660 W MORSE BOULEVARD, WINTER PARK
3 bd · 3.5 ba · 3,286 sqft
$2,695,000
413 W MORSE BOULEVARD, WINTER PARK
3 bd · 3.5 ba · 3,048 sqft
$1,399,000
512 W SWOOPE AVENUE, WINTER PARK
3 bd · 2.5 ba · 2,585 sqft
$849,000
437 N CAPEN AVENUE, WINTER PARK
3 bd · 2.5 ba · 1,904 sqft
$750,000
300 CAROLINA AVENUE UNIT 402C, WINTER PARK
3 bd · 2 ba · 1,350 sqft
$1,800,000$2,000,000
723 SYMONDS AVENUE, WINTER PARK
4 bd · 4 ba · 3,065 sqft
$649,900$675,000
840 W CANTON AVENUE, WINTER PARK
3 bd · 2 ba · 1,370 sqft
$2,650,000$2,800,000
541 W CANTON AVENUE, WINTER PARK
4 bd · 3.5 ba · 3,553 sqft
$695,000$750,000
432 W SWOOPE AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,317 sqft
Every active listing inside the Hannibal Square boundary
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Browse Hannibal Square
By feature — on the live map
Where the market lives
The numbers that matter
The Hannibal Square market
19
Sold, last 12 months
$550,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
19 days
Median time to sell
Hannibal Square vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 43.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Hannibal Square boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Hannibal Square is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Hannibal Square home
≈ $7,494/mo
$1,124,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$463/mo
Median HOA
From current listings inside the boundary
$2,400/mo
Median rent
Homes for rent inside the boundary
Population
1,798
Median age
38
Median income
$50,175
Median home value
$528,038
Beyond the listings
Living in Hannibal Square
Food & Drink
Top 3% 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.
Hobbies & Interests
Top 3% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Hobbies & Interests
Top 4% 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.
Appearance oriented
Top 4% 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.
Lifestyles
Top 4% 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.
Appearance oriented
Top 4% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
People who close here
Our Winter Park experts
Straight answers
Hannibal Square FAQs
Is Hannibal Square a good place to live?+
It's one of the most walkable spots in Orange County, with downtown Winter Park's dining and shopping steps away and downtown Orlando about 18 minutes out. Homes are assigned to Winter Park High and Audubon Park School. If you value a real neighborhood feel over sprawl, it delivers.
Is Hannibal Square expensive?+
It sits at the higher end of the market — the median list price is $1,124,000, and five of the ten active listings are above $1M. That said, actual sales over the past year came in at a median of $550,000, so pricing varies widely depending on the home. Compare with Lake Killarney if you want a sense of the surrounding range.
What do homes cost in Hannibal Square?+
Active listings run from $649,900 up to $2,800,000, with an average of $566 per square foot and a median home size around 2,594 square feet. Over the last 12 months, 19 homes sold at a median price of $550,000. The gap between list and sold prices reflects a mix of larger new builds and smaller historic homes.
How is the market in Hannibal Square?+
It's a small but active market — 10 homes are listed now and 19 closed in the past year, with a median of 29 days on market. Sellers are averaging 96% of their asking price, which points to steady, competitive demand. Buyers should be prepared to move decisively on the right listing.
What about HOA fees and property taxes?+
Median HOA dues run about $463 per month, though that varies by community and building. Property taxes come in around $10,792 per year at current values. For rentals, the median in the area is about $2,400 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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