Neighborhood · Sarasota, Florida
Oyster Bay Estates
Waterfront luxury minutes from downtown Sarasota
7
Homes for sale
$5,595,000
Median list price
$1,277
Avg price / sqft
200
Median days on market
Oyster Bay Estates sits on Sarasota's bayfront, a low-key enclave of estate homes where waterfront lots and deep-water access set the tone. It's close enough to reach Lido Key beaches and the arts and dining of the Rosemary District in minutes, yet quiet enough to feel like its own world. Neighboring pockets like Indian Beach / Sapphire Shores round out this stretch of upscale, water-adjacent Sarasota living.
This is a genuine luxury market: just 7 homes are active, with a median list price of $5,595,000 and asking prices running all the way to $26,400,000. Homes here take time to trade — a median of 200 days on market — and over the past year 8 sales closed at a median of $2,070,000. If you're comparing against the broader Sarasota homes for sale, expect fewer options here but far more waterfront and privacy per address.
Oyster Bay Estates is a community in Sarasota, Florida.
Quick facts
$4,400,000 – $26M price range
4,866 sqft median home
$21/mo median HOA
9 sold in 12 months
On the market now
Homes for sale in Oyster Bay Estates
$26,400,000
1310 S LAKE SHORE DRIVE, SARASOTA
4 bd · 5 ba · 10,697 sqft
$4,995,000$5,800,000
1804 N LAKE SHORE DRIVE, SARASOTA
4 bd · 4.5 ba · 6,854 sqft
$5,595,000
1429 N LAKE SHORE DRIVE, SARASOTA
5 bd · 6 ba · 4,545 sqft
$4,695,000
1421 N LAKE SHORE DRIVE, SARASOTA
4 bd · 5 ba · 4,217 sqft
$6,495,000$6,695,000
1137 N LAKE SHORE DRIVE, SARASOTA
6 bd · 6.5 ba · 6,462 sqft
$5,980,000$6,290,000
1521 S LAKE SHORE DRIVE, SARASOTA
4 bd · 6 ba · 4,866 sqft
$4,400,000
4431 CAMINO REAL, SARASOTA
4 bd · 4.5 ba · 3,787 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
9
Sold, last 12 months
$2,125,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
55 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
▼ 40.8% 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
≈ $31,566/mo
$5,595,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$21/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 bayfront enclaves, prized for waterfront estates, pools, and quick access to Lido Key beaches and downtown. Assigned schools include Phillippi Shores Elementary, Brookside Middle, and Riverview High. The pace is quiet and residential despite being minutes from the action.
Is Oyster Bay Estates expensive?+
Yes — this is a top-tier luxury market where all 7 active listings are priced above $1M. The median list price is $5,595,000, and homes average $1,277 per square foot, well above most of Sarasota.
What do homes cost in Oyster Bay Estates?+
Active listings range from $4,400,000 to $26,400,000 with a median of $5,595,000, and the median home is about 4,866 square feet. Over the past 12 months, 8 homes actually sold at a median of $2,070,000, so closed prices land well below current asking on the smaller end of the spectrum.
How is the market in Oyster Bay Estates?+
Inventory is thin at 7 active homes, and properties sit a median of 200 days on market — typical for a high-end, low-volume neighborhood. Sellers average 92% of their asking price, so there's real room to negotiate on the right listing.
What about HOA fees and property taxes?+
HOA costs are minimal here, with a median of just $21 per month. Property taxes are the bigger line item, running a median of $22,275 per year in line with the neighborhood's high values.
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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