Neighborhood · Key West, Florida
South Old Town
Historic streets, walkable blocks, real island living
3
Homes for sale
$1,100,000
Median list price
$846
Avg price / sqft
405
Median days on market
South Old Town sits at the heart of Key West's most walkable stretch, where historic architecture and shaded streets set the pace of daily life. It's the kind of neighborhood where you leave the car parked and cover the day on foot, close to the character that makes Key West what it is. The nearby New Town community rounds out the surrounding options for buyers weighing where on the island to land.
The market here is genuinely thin — just 3 active listings right now, with a median list price of $1,100,000 and prices running from $799,000 up to $1,799,000. Homes move slowly, with a median 405 days on market, so buyers who watch the live map closely have room to be patient and deliberate. Assigned schools include Horace O'Bryant School and Key West High School, which matters for families settling in for the long haul.
South Old Town is a community in Key West, Florida.
Quick facts
$799,000 – $1.8M price range
1,344 sqft median home
1 sold in 12 months
On the market now
Homes for sale in South Old Town
$799,000
1425 Eliza Street, Key West FL 33040, KEY WEST
3 bd · 1 ba · 1,342 sqft
$1,100,000
414 Virginia Street, Key West FL 33040, KEY WEST
3 bd · 2 ba · 1,344 sqft
$1,799,000
1011 Simonton Street # 1, Key West FL 33040, KEY WEST
3 bd · 2.5 ba · 1,600 sqft
Every active listing inside the South Old Town boundary
Open full map search →Find your fit
Browse South Old Town
By feature — on the live map
Where the market lives
The numbers that matter
The South Old Town market
1
Sold, last 12 months
$1,920,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
318 days
Median time to sell
South Old Town vs Key West
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the South Old Town boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools South Old Town is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median South Old Town home
≈ $6,239/mo
$1,100,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
1,955
Median age
47
Median income
$86,255
Median home value
$816,561
Beyond the listings
Living in South Old Town
Hobbies & Interests
Top 2% in the U.S.Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
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.
Hobbies & Interests
Top 15% in the U.S.Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
Culture
Top 23% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Entertainment
Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Lifestyles
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.
Straight answers
South Old Town FAQs
Is South Old Town a good place to live?+
It's one of the most walkable parts of Key West, with historic streets that put daily errands and island life within a short stroll. Families are assigned to Horace O'Bryant School and Key West High, and the neighborhood's compact scale keeps it feeling residential.
Is South Old Town expensive?+
Yes — this is a premium island market, with a median list price of $1,100,000 and an average of $846 per square foot. Two of the three current listings are priced above $1 million, so budgets here start high.
What do homes cost in South Old Town?+
Active listings range from $799,000 to $1,799,000, with a median list price of $1,100,000 on homes around 1,344 square feet. The one sale in the past 12 months closed at $1,920,000, which shows how much larger or standout properties can command.
How is the market in South Old Town?+
Inventory is very tight, with just 3 active listings and only 1 sale in the last 12 months. Homes take a median 405 days to sell, and sellers have averaged 96% of asking — so it's a slow, deliberate market where patience pays. You can track new listings on the live map.
What about HOA fees and property taxes?+
HOA data isn't available for the current South Old Town listings, which reflects the neighborhood's mix of standalone historic homes. The median property tax runs about $2,798 per year, though your figure depends on the specific property and assessment.
Keep exploring
More Key West 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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