Neighborhood · Winter Park, Florida
Hannibal Square
Walkable history meets Winter Park's best dining
12
Homes for sale
$1,074,500
Median list price
$695
Avg price / sqft
109
Median days on market
Hannibal Square sits at the western edge of downtown Winter Park, a historic community where brick streets and century-old cottages share blocks with restaurants, galleries, and the kind of sidewalk life you can actually walk to. It's steps from Park Avenue and close to Lake Killarney, Orwin Manor, and the leafy residential pockets that give this part of Winter Park its character. Students are zoned for Winter Park High and Audubon Park School, and downtown Orlando is about 18 minutes away.
For buyers, this is a tightly held, higher-end market. There are just 11 active listings with a median list price of $1,300,000, and six of those are priced above $1M — so expect a smaller selection and a premium for the location. Homes here take time to move (a median of 103 days), but sellers are still getting about 97% of asking, which tells you well-priced properties hold their value. If this pocket feels tight, nearby Eastbrook and Winter Park Pines can widen the search.
Hannibal Square is a community in Winter Park, Florida.
Quick facts
$649,900 – $4.0M price range
2,234 sqft median home
$677/mo median HOA
$2,500/mo median rent
20 sold in 12 months
Drive times
On the market now
Homes for sale in Hannibal Square
$699,000
250 CAROLINA AVENUE UNIT 202, WINTER PARK
3 bd · 2 ba · 1,450 sqft
$3,950,000
540 N PENNSYLVANIA AVENUE, WINTER PARK
4 bd · 2 ba · 1,652 sqft
$1,300,000
504 W SWOOPE AVENUE, WINTER PARK
3 bd · 2.5 ba · 2,563 sqft
$739,000
250 CAROLINA AVENUE UNIT 205, WINTER PARK
2 bd · 2 ba · 1,311 sqft
$649,900$675,000
840 W CANTON AVENUE, WINTER PARK
3 bd · 2 ba · 1,370 sqft
$2,695,000$2,800,000
660 W MORSE BOULEVARD, WINTER PARK
3 bd · 3.5 ba · 3,286 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
$2,625,000$2,695,000
413 W MORSE BOULEVARD, WINTER PARK
3 bd · 3.5 ba · 3,048 sqft
$1,600,000$1,700,000
723 SYMONDS AVENUE, WINTER PARK
4 bd · 4 ba · 3,065 sqft
$650,000$710,000
300 CAROLINA AVENUE UNIT 402C, WINTER PARK
3 bd · 2 ba · 1,350 sqft
$680,000$695,000
432 W SWOOPE AVENUE, WINTER PARK
4 bd · 3.5 ba · 2,664 sqft
Every active listing inside the Hannibal Square boundary
Open full map search →Find your fit
Browse Hannibal Square
By feature — on the live map
Where the market lives
The numbers that matter
The Hannibal Square market
20
Sold, last 12 months
$572,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
11 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
▼ 11.5% 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
≈ $7,456/mo
$1,074,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$677/mo
Median HOA
From current listings inside the boundary
$2,500/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 addresses in Winter Park, with Park Avenue's restaurants and galleries right next door and zoning for Winter Park High and Audubon Park School. Downtown Orlando is about 18 minutes out, and nearby communities like Lake Killarney add to the appeal. It suits buyers who want historic character and a true neighborhood feel close to the city.
Is Hannibal Square expensive?+
Yes — it's a premium market. The median list price is $1,300,000, with six of the 11 active listings priced above $1M and an average of $715 per square foot. Prices run from about $649,900 up to $3,950,000.
What do homes cost in Hannibal Square?+
Active listings range from roughly $649,900 to $3,950,000, with a median list price of $1,300,000 on a median home size of 2,563 sqft. Over the past 12 months, 19 homes sold at a median price of $550,000, which reflects a mix of smaller and larger properties.
How is the market in Hannibal Square right now?+
It's a tightly held, slower-moving market — homes sit a median of 103 days, and only 11 are currently active. That said, sellers are averaging about 97% of their asking price, so well-priced homes still find buyers. If options feel limited, check Eastbrook nearby.
What about HOA fees and property taxes?+
The median HOA runs about $651 per month, and the median annual property tax is around $11,943, both reflecting the higher-end nature of the area. If you're weighing a rental first, the median rent here is about $2,750 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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