Neighborhood · Osprey, Florida
Oaks
Gated luxury living between Sarasota and Venice
15
Homes for sale
$1,950,000
Median list price
$483
Avg price / sqft
180
Median days on market
The Oaks is a cluster of established, largely gated communities along the Osprey stretch of the Gulf Coast, where wide lots, mature landscaping and access to the water shape everyday life. Neighborhoods like Southbay Yacht & Racquet Club draw boaters, while Rivendell and Bay Oaks Estates offer more traditional single-family settings a short drive from both downtown Sarasota and Venice. It's the kind of place families choose for space and privacy without giving up proximity to the coast.
For a buyer today, this is a luxury market with room to negotiate. Among the 16 active Osprey homes for sale in this area, the median list price sits at $1,799,500, and homes have been taking a while to move — a median of 175 days on market. Over the last year 27 homes sold at a median of $1,850,000, with sellers collecting about 92% of asking, so there's real space to make a considered offer.
Oaks is a community in Osprey, Florida.
Quick facts
$235,000 – $4.8M price range
4,012 sqft median home
$475/mo median HOA
$2,375/mo median rent
27 sold in 12 months
On the market now
Homes for sale in Oaks
View all 15 →
$275,000
51 MACEWEN DRIVE UNIT 12, OSPREY
1 bd · 1 ba · 623 sqft
$1,649,000
75 OSPREY POINT DRIVE, OSPREY
4 bd · 4 ba · 4,001 sqft
$4,790,000
101 OSPREY POINT DRIVE, OSPREY
4 bd · 5.5 ba · 5,087 sqft
$235,000$300,000
51 MACEWEN DRIVE UNIT 5, OSPREY
1 bd · 1 ba · 595 sqft
$285,000
51 MAC EWEN DRIVE UNIT 14, OSPREY
1 bd · 1 ba · 595 sqft
$1,950,000
97 SUGAR MILL DRIVE, OSPREY
5 bd · 5.5 ba · 4,885 sqft
$1,500,000$1,535,000
480 ORISKANY COURT, OSPREY
3 bd · 3.5 ba · 3,208 sqft
$1,950,000$2,100,000
538 DOVE POINTE DRIVE, OSPREY
4 bd · 5.5 ba · 4,346 sqft
$2,399,000$2,500,000
49 OSPREY POINT DRIVE, OSPREY
4 bd · 3.5 ba · 3,953 sqft
$2,189,000$2,250,000
433 E MACEWEN DRIVE, OSPREY
4 bd · 3.5 ba · 4,012 sqft
$1,445,000$1,495,000
422 BLUE GARDEN LANE, OSPREY
3 bd · 3.5 ba · 3,872 sqft
$3,640,000$3,690,000
854 MACEWEN DRIVE, OSPREY
4 bd · 5 ba · 9,081 sqft
Every active listing inside the Oaks boundary
Open full map search →Find your fit
Browse Oaks
By feature — on the live map
Where the market lives
The numbers that matter
The Oaks market
27
Sold, last 12 months
$1,850,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
33 days
Median time to sell
Oaks vs Osprey
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 23.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Oaks home
≈ $12,037/mo
$1,950,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$475/mo
Median HOA
From current listings inside the boundary
$2,375/mo
Median rent
Homes for rent inside the boundary
Population
1,061
Median age
63
Median income
$98,734
Median home value
$983,226
Beyond the listings
Living in Oaks
Beliefs
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.
Culture
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.
Hobbies & Interests
Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
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.
Active
Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
Beliefs
Conservation
Good stewards of the earth, this population advocates for a cleaner environment and responsible use of resources. They often encourage others to recycle and use clean energy.
Straight answers
Oaks FAQs
Is The Oaks a good place to live?+
It suits buyers who want space, privacy and access to the water — most homes here sit inside gated communities like Sarabay Acres, and 12 of 16 active listings include a pool. Families also value the assigned schools and the location between Sarasota and Venice.
Is it expensive to buy here?+
Yes, this is a luxury market. The median list price is $1,799,500, and 12 of the 16 active listings are priced above $1 million, with the range running from $235,000 up to $4,790,000.
What do homes cost in The Oaks?+
The median list price is $1,799,500 and homes average about $477 per square foot on a median size of roughly 4,007 square feet. Over the past 12 months, 27 homes sold at a median price of $1,850,000.
How is the market right now?+
It favors patient, prepared buyers. Homes are averaging 175 days on market, and sellers are getting about 92% of asking price, which leaves genuine room to negotiate — you can track new listings on the live map.
What about HOA fees and property taxes?+
The median HOA runs about $475 per month, which reflects the gated, amenity-driven communities such as Southbay Yacht & Racquet Club. Median annual property tax is around $12,898, in line with the area's higher home values.
Keep exploring
More Osprey 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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