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Search The Oaks Real Estate Listings, Over $1,000,000

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75 Osprey Point Drive, OSPREY, FL
$1,975,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,001 SQFT
  • 18 DOM
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**stunning Architectural Estate In The Coveted Oaks Bayside Country Club Neighborhood** On Sarasota Bay Waters… Situated On Two Lots Totaling Over 3/4 Acres, The Main House On Lot #1 Features 3 Beds / 3 Baths While The Separate Guest House On Adja...

49 Osprey Point Drive, OSPREY, FL
$2,595,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,953 SQFT
  • 24 DOM
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Nestled In The Prestigious Gated Enclave Of The Oaks Bayside In Sarasota, This Sedona-inspired Retreat Was Recently Updated From Wall To Wall Creating A Like Brand New Home. The Estate Seamlessly Blends Modern Luxury, Comfort, And Serenity. With A...

385 N Point Road 704, OSPREY, FL
$1,500,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 27 DOM
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Experience Breathtaking Views Of The Bay And Gulf From This Spacious 3 Bedroom, 3 Bath End Unit, Featuring A Separate Dining Room And Den. Completely Updated And Meticulously Maintained, This Unit Is Beautifully Appointed And Custom Features Aboun...

538 Dove Pointe Drive, OSPREY, FL
$2,300,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,346 SQFT
  • 30 DOM
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**elegant Updated Residence In The Oaks | Modern Comfort On A .83-acre Corner Lot** Welcome To 538 Dove Pointe, An Exceptional Residence In The Secure And Gated Oaks Country Club Community In Osprey, Florida. Set On A Generous .83-acre Elevated L...

691 Eagle Watch Lane, OSPREY, FL
$3,995,000

Residential, Single Family Residence
  • 4 Beds
  • 7 Baths
  • 6,705 SQFT
  • 32 DOM
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Nestled Within The Exclusive Gated Community Of The Oaks Club In Osprey, Florida. This Singular Estate Represents A Masterful Confluence Of Architectural Refinement And Modern Luxury, Encompassing Nearly 7000 Ft.² Of Conditioned Living Space, The ...

Photo of Listing #A4670240

325 Osprey Point Drive, OSPREY, FL
$1,690,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 3,905 SQFT
  • 37 DOM
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Under Contract-accepting Backup Offers. **beautifully Updated Country Club Estate With Ideal Southern Exposure And Water View** Is Located In The Coveted, Oaks Bayside Country Club Neighborhood On Little Sarasota Bay. Enjoy The Private And Tranqui...

889 Macewen Drive, OSPREY, FL
$2,300,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,235 SQFT
  • 39 DOM
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**incredible Transformation Of This Move-in Ready, Golf Course Estate** From The Reimagined Entryway And Through The Stunning Iron Double Front Door, You Will Be Captivated By The Attention To Detail Throughout This Elegantly Appointed Residence ...

Photo of Listing #A4669572

453 E Macewen Drive, OSPREY, FL
$1,899,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,191 SQFT
  • 43 DOM
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Under Contract-accepting Backup Offers. Set An Appointment To Experience This Thoughtfully Designed Arthur Rutenberg Home, Where Craftsmanship And Details Are Truly On Display. Upon Entering Through The Double Door Entrance, The Quality And Attent...

Photo of Listing #A4668401

385 N Point Road 903, OSPREY, FL
$1,100,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 46 DOM
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One Or More Photo(s) Has Been Virtually Staged. From The Moment The Private Elevator Doors Open, The Panorama Of The View Has You At ‘hello,” With A Northwest-facing Expanse Over The Preserve, The Lagoon Below, Sarasota Bay And The Gulf Beyond. Th...

600 Eagle Watch Lane, OSPREY, FL
$2,195,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,681 SQFT
  • 47 DOM
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One Or More Photo(s) Has Been Virtually Staged. **brilliantly Updated, Move-in Ready, Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Offers An Ideal Southern-exposure And View Across The 3rd Fairway Of The Interior, He...

Photo of Listing #A4664295

133 Osprey Point Drive, OSPREY, FL
$1,500,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 3,679 SQFT
  • 49 DOM
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One Or More Photo(s) Has Been Virtually Staged. Custom Home Located In The Exclusive Gated Community Of The Oaks Bayside With A Private Pool And Spa. Just Across The Street From Sarasota Bay. Recent Improvements Include Updated Bathrooms And A New...

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Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on December 8th, 2025 at 12:58am EST.