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33 Bishops Court Road 118, OSPREY, FL
$695,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,890 SQFT
  • 46 DOM
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Come And Enjoy The Perfect Maintenance Free Lifestyle In This Exquisite Townhouse Located In One Of The Finest Country Clubs On The Gulf Coast, The Oaks Golf And Country Club. Previously Redesigned, This Tuscan Style Home In The Quaint And Charm...

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...

854 Macewen Drive, OSPREY, FL
$3,950,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 50 DOM
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One Or More Photo(s) Has Been Virtually Staged. Set On A Private Cul-de-sac Within The Oaks, This Revitalized Estate Captures The Essence Of Elegant Florida Living. From The Moment You Enter, The Home’s Light-filled, Open Design And Thoughtful Upd...

393 N Point Road 1002, OSPREY, FL
$2,350,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 3,738 SQFT
  • 55 DOM
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Experience Unmatched Luxury In This Meridian Penthouse! Welcome To The Epitome Of Luxury Living At Meridian At The Oaks Preserve. This Stunning 3 Bedroom, 2.5 Bath Penthouse Offers A Private 2-car Garage And Is Designed For The Discerning Buyer Wh...

85 Sugar Mill Drive, OSPREY, FL
$2,150,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 4,191 SQFT
  • 59 DOM
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**stunningly Designed And Updated -- Architectural Estate In The Coveted Oaks Bayside Country Club Neighborhood** On Little Sarasota Bay Waters Features 3 Beds Plus Den/office, 3 Full Baths And Incredible Detail Throughout Including Beautiful Crow...

147 Osprey Point Drive, OSPREY, FL
$750,000

Your Dream Homesite Awaits! This Lot Is Located Within The Oaks Bayside, One Of Southwest Florida‘s Most Exclusive Private, Gated Communities. This Amazing Property Is Near The Community Dock And Fountain And Is Surrounded By Some Of The Most Gran...

370 Sugar Mill Drive, OSPREY, FL
$2,650,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,783 SQFT
  • 80 DOM
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**meticulously Maintained, Architectural Perfection, This Bright, Spectacular Estate Featuring Incredibly Spacious First Floor Living Space, With 5-beds, 6.5 Baths, Private Second Floor Family, Au Pair And/or Guest Quarters, New Pool, Ideal Flood ...

101 Osprey Point Drive, OSPREY, FL
$5,000,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 5,087 SQFT
  • 81 DOM
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A Grand Estate Where Timeless Design Meets Lakefront Tranquility, 101 Osprey Point Drive Offers Refined Living Within The Private Gates Of The Oaks Bayside. Designed By Architect Bo Macewen, This One-of-a-kind Home Spans More Than 5,000 Square Fee...

105 Turquoise Lane, OSPREY, FL
$995,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,606 SQFT
  • 114 DOM
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Welcome To Emerald Woods, A Desired Cul-de-sac Within The Oaks Preserve, And This Private Lee Wetherington Custom Home That Will Check All The Boxes, And More. Situated On One Of The Largest Lots And Surrounded By Preserve For Privacy, You’ll Fi...

401 N Point Road 304, OSPREY, FL
$900,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 131 DOM
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Give Yourself The Gift Of Refined Living In This Expansive 2,778 Square Foot Residence—the Largest Non-penthouse Floor Plan Available In Meridian At The Oaks Preserve. Every Detail In This Meticulously Maintained, And Beautifully Updated Condomini...

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

Listing information last updated on December 8th, 2025 at 2:43am EST.