Neighborhood · Sarasota, Florida
Oyster Bay Estates
Waterfront luxury minutes from downtown Sarasota
4
Homes for sale
$8,677,500
Median list price
$1,384
Avg price / sqft
284
Median days on market
Oyster Bay Estates sits along the bayfront just south of downtown Sarasota, a quiet enclave of generously scaled homes on deep lots, many with direct water access and private docks. It's an address for buyers who want proximity to the city's culture and the Gulf without living in the middle of either — a short hop to Lido Key's beaches and the galleries and restaurants of the Rosemary District, yet tucked into its own leafy pocket. Neighboring communities like Arlington Park round out the area with parks and everyday amenities.
This is a genuine luxury market, and the numbers reflect it: just four active listings with a median list price of $8,677,500, ranging from $4,995,000 up to $26,400,000. Over the past year ten homes sold at a median of $2,132,500, with sellers collecting about 93% of asking — so there's real room to negotiate. With a median 252 days on market, buyers here have time to be deliberate.
Oyster Bay Estates is a community in Sarasota, Florida.
Quick facts
$4,995,000 – $26M price range
8,544 sqft median home
$25/mo median HOA
10 sold in 12 months
Drive times
On the market now
Homes for sale in Oyster Bay Estates
$11,375,000
1136 N LAKE SHORE DRIVE, SARASOTA
4 bd · 7 ba · 10,234 sqft
$4,995,000$5,800,000
1804 N LAKE SHORE DRIVE, SARASOTA
4 bd · 4.5 ba · 6,854 sqft
$26,400,000
1310 S LAKE SHORE DRIVE, SARASOTA
4 bd · 5 ba · 10,697 sqft
$5,980,000$6,290,000
1521 S LAKE SHORE DRIVE, SARASOTA
4 bd · 6 ba · 4,866 sqft
Every active listing inside the Oyster Bay Estates boundary
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Browse Oyster Bay Estates
By feature — on the live map
The numbers that matter
The Oyster Bay Estates market
10
Sold, last 12 months
$2,132,500
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
50 days
Median time to sell
Oyster Bay Estates vs Sarasota
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 9.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Oyster Bay Estates boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Oyster Bay Estates is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Oyster Bay Estates home
≈ $48,990/mo
$8,677,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$25/mo
Median HOA
From current listings inside the boundary
Population
427
Median age
45
Median home value
$1,522,100
Beyond the listings
Living in Oyster Bay Estates
Entertainment
Top 11% in the U.S.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.
Food & Drink
Top 12% in the U.S.Trendy Eats
Meals are a social experience, and these foodies take it to the next level. This population can't wait to snap a pic of their plate and share it before chowing down.
Food & Drink
Top 12% in the U.S.Wine Lovers
It's all about the grape. This population enjoys a trip to the vineyard to learn about wine and sharing a good bottle with friends and family.
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 13% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Beliefs
Top 14% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Straight answers
Oyster Bay Estates FAQs
Is Oyster Bay Estates a good place to live?+
It's one of Sarasota's premier waterfront enclaves, prized for large private lots, bay access, and a location minutes from downtown and the Gulf beaches at Lido Key. Assigned schools include Phillippi Shores Elementary, Brookside Middle, and Riverview High. The low-density, tucked-away character appeals to buyers who want luxury without a busy main-road setting.
Is Oyster Bay Estates expensive?+
Yes — this is a top-tier luxury market. The median list price is $8,677,500 and active homes range from $4,995,000 to $26,400,000, with an average of about $1,384 per square foot. Even the median sold price over the past year came in at $2,132,500.
What do homes cost in Oyster Bay Estates?+
Currently there are four active listings with a median list price of $8,677,500, spanning $4,995,000 to $26,400,000. Homes are large, with a median size around 8,544 square feet, and they trade at roughly $1,384 per square foot. Actual sold prices over the last year had a median of $2,132,500.
How is the market right now?+
It's a slow, deliberate luxury market with only four active listings and a median 252 days on market. Ten homes sold over the past 12 months, and sellers averaged about 93% of their asking price — meaning there's meaningful negotiating room for a patient buyer.
What about HOA fees and property taxes?+
HOA costs are minimal here, with a median of about $25 per month. Property taxes, however, reflect the home values — the median annual tax bill is around $36,415, so buyers should factor that into their carrying costs.
Keep exploring
More Sarasota 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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