Neighborhood · Osprey, Florida
Oaks
Gated Gulf-coast living between Sarasota and Venice
15
Homes for sale
$1,700,000
Median list price
$503
Avg price / sqft
121
Median days on market
The Oaks sits in Osprey along Sarasota County's Gulf coast, a collection of gated enclaves where privacy and space are the whole point. Ten of the twelve active listings are gated and nine come with a pool, so you're looking at estate-scale homes on quiet streets — the median house here runs 4,294 square feet. Communities like Rivendell, Sarabay Acres and Southbay Yacht & Racquet Club each have their own character, from wooded lots to boater's access.
For a buyer today, this is a high-end market with room to negotiate. The median list price is $1,925,000, but the range runs wide — from $235,000 to $4,790,000 — and with 28 homes sold in the past year at a median of $1,800,000, sellers are landing about 92% of asking. Homes take a median 84 days to sell, so patience and a sharp offer both pay off. Browse the full picture on the live map or across Osprey homes for sale.
Oaks is a community in Osprey, Florida.
Quick facts
$235,000 – $4.8M price range
4,001 sqft median home
$475/mo median HOA
$2,375/mo median rent
29 sold in 12 months
Drive times
On the market now
Homes for sale in Oaks
View all 15 →
$1,590,000
402 MACEWEN DRIVE, OSPREY
3 bd · 3.5 ba · 3,565 sqft
$2,175,000
362 MACEWEN DRIVE, OSPREY
4 bd · 3.5 ba · 4,117 sqft
$1,700,000
141 SUGAR MILL DRIVE, OSPREY
3 bd · 3 ba · 3,118 sqft
$1,495,000
226 SAINT JAMES PARK, OSPREY
3 bd · 2.5 ba · 2,591 sqft
$235,000$300,000
51 MACEWEN DRIVE UNIT 5, OSPREY
1 bd · 1 ba · 595 sqft
$1,595,000$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
$275,000
51 MACEWEN DRIVE UNIT 12, OSPREY
1 bd · 1 ba · 623 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
$2,399,000$2,500,000
49 OSPREY POINT DRIVE, OSPREY
4 bd · 3.5 ba · 3,953 sqft
$1,950,000$2,100,000
538 DOVE POINTE DRIVE, OSPREY
4 bd · 5.5 ba · 4,346 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
29
Sold, last 12 months
$1,850,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
54 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
▼ 28.6% 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
≈ $10,720/mo
$1,700,000 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's a strong fit if you want gated privacy and space on Sarasota County's Gulf coast — ten of twelve active listings are gated and most include pools. Assigned schools include Laurel Nokomis School and Venice Senior High School. Downtown Tampa is about 75 minutes away, so it stays quiet without feeling isolated.
Is The Oaks expensive?+
Yes, this is a high-end market — the median list price is $1,925,000 and nine of the twelve active homes are priced above $1 million. That said, the range runs from $235,000 up to $4,790,000, so there's more variety than the median suggests. Communities like Bay Oaks Estates sit at the pricier end of that spectrum.
What do homes cost in The Oaks?+
Active listings carry a median price of $1,925,000 at an average of $481 per square foot, on homes that median around 4,294 square feet. Over the past 12 months, 28 homes sold at a median price of $1,800,000. Rentals run a median of $2,375 a month.
How is the market right now?+
There are 12 active listings and homes are taking a median of 84 days to sell, so it's a patient market that rewards a well-researched offer. Sellers are getting about 92% of asking on average, which leaves real room to negotiate. Watch inventory move in Rivendell and the other enclaves as new listings appear.
What are HOA fees and property taxes like?+
Expect a median HOA of about $479 per month, which reflects the gated, amenity-oriented communities here. Property taxes run a median of roughly $12,898 per year, in line with the neighborhood's estate-scale values. Fees vary by community, so confirm the specifics for any home you tour.
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.
Never miss a listing
New Oaks homes, in your inbox
A daily digest of new Osprey listings — straight from the MLS. Unsubscribe anytime.