Neighborhood · Winter Park, Florida
Hannibal Square
Historic streets steps from Park Avenue's best
11
Homes for sale
$849,000
Median list price
—
Avg price / sqft
—
Median days on market
Hannibal Square sits on the west side of Winter Park, a walkable pocket with real history and a genuine Main Street feel where restaurants, galleries, and small shops are part of daily life rather than a weekend destination. It's the kind of neighborhood where you can leave the car parked, and downtown Orlando is only about 18 minutes away when you do need it. Nearby you'll find established communities like Lake Killarney and Kenilworth, each with its own character.
For buyers today, this is a tight, high-demand market: 11 homes are active right now with a median list price of $849,000. Inventory turns over quietly here, so serious buyers should be ready to move when the right home lists. Assigned schools include Winter Park High and Audubon Park School, a draw for families weighing nearby options like Winter Park Pines and Eastbrook.
Hannibal Square is a community in Winter Park, Florida.
Quick facts
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
$839,000
730 W SWOOPE AVENUE, WINTER PARK
5 bd · 3 ba · 2,132 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
$1,800,000$2,000,000
723 SYMONDS AVENUE, WINTER PARK
4 bd · 4 ba · 3,065 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
$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
Open full map search →The numbers that matter
The Hannibal Square market
Hannibal Square vs Winter Park
Median list price
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
≈ $5,461/mo
$849,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
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.
On the calendar
Near Hannibal Square
Jul
14
Tue
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
14
Tue
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
Jul
14
Tue
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
14
Tue
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
14
Tue
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
Jul
16
Thu
Thursday Thinks Trivia
7:30pm
This challenging trivia night promises a wide range of engaging questions, ensuring something new and exciting for everyone - from pop culture, geography, and history, to…
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 more walkable spots in Winter Park, with restaurants, shops, and galleries close enough to reach on foot. Downtown Orlando is about 18 minutes away and Universal Orlando roughly 28, so you get a real neighborhood feel without giving up access to the rest of Central Florida.
Is Hannibal Square expensive?+
Yes, it sits at the upper end of the Winter Park market, with a current median list price of $849,000 across the 11 active listings. Its walkable location and historic character keep demand strong, which supports those prices.
What do homes cost in Hannibal Square?+
Right now there are 11 homes on the market with a median list price of $849,000. Because inventory is limited, pricing can move quickly, so it's worth comparing against nearby areas like Lake Killarney to understand the full range.
How is the market in Hannibal Square?+
It's a low-inventory market with 11 active listings and a median list price of $849,000. Homes here tend to sell quietly and don't linger, so buyers should be prepared to act when something that fits comes up.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available for the current Hannibal Square listings, which is common in an established, non-master-planned neighborhood. Your agent can pull the exact tax and any HOA details on a home-by-home basis, and comparing to communities like Winter Park Pines can help set expectations.
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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