Neighborhood · Sarasota, Florida
Oyster Bay Estates
Waterfront luxury minutes from downtown Sarasota
9
Homes for sale
$4,995,000
Median list price
$1,162
Avg price / sqft
229
Median days on market
Oyster Bay Estates sits just south of downtown Sarasota, a low-key enclave where deep-water lots, mature landscaping, and quiet streets sit within a short drive of the bay and the beaches. It's the kind of address that draws people who want space and privacy without giving up quick access to Lido Key, the shops and galleries of the Rosemary District, and the walkable core near Five Points. Families lean on assigned schools like Phillippi Shores Elementary and Riverview High, and boaters value the canal-and-bay frontage that defines the neighborhood.
This is firmly a luxury market, and buyers should come in eyes open. Nine homes are active with a median list price of $4,995,000 and a range that stretches from $2,095,000 all the way to $26,400,000, so pricing here spans a wide gulf. Homes take time to move — a median of 229 days on market — and over the last year sellers netted about 92% of asking, which leaves real room to negotiate. If Oyster Bay's numbers run high, comparing nearby options like Arlington Park or the broader pool of Sarasota homes for sale is a smart next step.
Oyster Bay Estates is a community in Sarasota, Florida.
Quick facts
$2,095,000 – $26M price range
4,545 sqft median home
$21/mo median HOA
9 sold in 12 months
Drive times
On the market now
Homes for sale in Oyster Bay Estates
$2,095,000
1511 N LAKE SHORE DRIVE, SARASOTA
4 bd · 3.5 ba · 3,613 sqft
$3,100,000
1556 EASTBROOK DRIVE, SARASOTA
3 bd · 3 ba · 3,307 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
$26,400,000
1310 S LAKE SHORE DRIVE, SARASOTA
4 bd · 5 ba · 10,697 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
▼ 42.9% 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
≈ $28,132/mo
$4,995,000 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 a quiet, established luxury neighborhood just south of downtown Sarasota, prized for its waterfront lots and short drives to the bay and beaches. Buyers who want privacy with easy access to Lido Key and the walkable downtown core find the location hard to beat. Assigned schools include Phillippi Shores Elementary and Riverview High School.
Is Oyster Bay Estates expensive?+
Yes — this is one of Sarasota's premium markets. The median list price is $4,995,000, all nine active listings are priced above $1M, and homes average about $1,162 per square foot on a median size of 4,545 square feet.
What do homes cost in Oyster Bay Estates?+
Active listings span from $2,095,000 to $26,400,000, with a median list price of $4,995,000. Over the last 12 months, nine homes sold at a median price of $2,125,000, so realized sale prices often land below the top of the list range. For lower price points, it's worth also watching nearby Indian Beach / Sapphire Shores.
How is the market right now?+
It moves slowly and favors patient, prepared buyers. The median home spends 229 days on market, and over the past year sellers accepted about 92% of asking on average — meaningful negotiating room at this price tier. With only nine active listings and nine sold in the last year, inventory turns over deliberately.
What about HOA fees and property taxes?+
The HOA burden is minimal here, with a median of about $21 per month. Property taxes are the bigger line item, running a median of roughly $18,994 per year, which reflects the neighborhood's high assessed 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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