Osprey Real Estate for Sale, Over $1,000,000

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Image 0: A4672081

403 Longbow Trail, OSPREY, FL - $1,095,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,770 SQFT
  • 269 DOM
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Welcome To This Beautifully Maintained 4 Bed, 3 Bath Property Nestled On A 2-acre Lot In One Of Osprey's Most Desirable Communities Pine Ranch. Located 15 Minutes From Siesta Key And Nokomis Beach And Is Within A Short Distance From The Nationally...

Image 1: A4678422

385 N Point Road 304, OSPREY, FL - $1,100,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,778 SQFT
  • 209 DOM
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**magnificently Updated, Expansive Corner Condo Residence Offering Nearly 2,800 Sq Ft Of Refined Living Space** Features 3 Bedrooms, 3 Full Baths, Plus A Study/den (or Optional 4th Bedroom With Walk-in Closet), All Nestled Behind The Secure Gates ...

Image 2: N6144070

14021 Bellagio Way 404, OSPREY, FL - $1,100,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,187 SQFT
  • 108 DOM
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This Beautifully Remodeled Waterfront Condominium In Osprey Offers A Blend Of Luxury, Comfort And Coastal Living, Set Directly On Little Sarasota Bay With Sweeping Tranquil Bay Views From The Fourth Floor. The Residence Features Three Spacious Bed...

Image 3: A4688266

1527 Buoy Lane, OSPREY, FL - $1,165,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,830 SQFT
  • 128 DOM
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Beautifully And Thoroughly Recently Updated Beach Style Home In Southbay Yacht And Racquet Club Featuring 10 Foot Ceilings. 2026 Ac Unit, 2024 Tile Roof, 2023 Driveway, Cabinets, Lighting, Appliances, Tile And Carpet Are Just The Beginning. 2023 P...

Image 4: A4667634

700 Faith Avenue, OSPREY, FL - $1,200,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,474 SQFT
  • 275 DOM
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Virtually Staged. Upon Passing The Gated Pillars Of The Winding Driveway You Come Upon A Hidden Treasure. 2.5 Acres Of Beauty Tucked Away Just Off Tamiami And Bay In Osprey. This Property Backs Up To The Renowned Pine View School Grades 2-12. One ...

Image 5: A4679994

409 N Point Road 601, OSPREY, FL - $1,250,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,594 SQFT
  • 191 DOM
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**fantastic Gulf And Bay Views From This Updated 6th-floor Corner Residence** This Spacious, Light-filled Corner Unit Offers Nearly 2,600 Sq. Ft. Of Living Space And Features 3 Bedrooms Plus A Study/den, 3 Full Baths, Two Elevator Banks, Two Assig...

Image 6: A4691664

156 Bishops Court Road, OSPREY, FL - $1,289,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,112 SQFT
  • 97 DOM
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One Or More Photo(s) Has Been Virtually Staged. Designed By Renowned Architect Frank Folsom Smith, This Timeless Residence Is Privately Positioned On An Expansive Double Lot At The End Of A Quiet Cul-de-sac Within The Oaks Preserve. The Property I...

Image 7: A4642397

3603 N Point Road 702, OSPREY, FL - $1,395,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,545 SQFT
  • 531 DOM
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**magnificent View From This 7th Floor, Penthouse Condo** Offering 3 En Suite Bedrooms, 3 Full Baths And A Treasured Private 2-car Garage! Located Behind The Gates Of The Highly Sought After Oaks-preserve, Country Club Neighborhood In The Newest M...

Image 8: A4695959

360 N Point Road, OSPREY, FL - $1,495,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,913 SQFT
  • 66 DOM
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Virtually Staged. A Unique Offering! This Like-new, Never Lived In Spanish Mission Style Home Is A Rare Find. Move In Ready And Set On A Private .63 Acre Lot In The Oaks Preserve, The Open Floor Plan Includes 3 En Suite Bedrooms And 3.5 Baths. Tho...

Image 9: A4621683

909 Macewen Drive, OSPREY, FL - $1,595,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,241 SQFT
  • 699 DOM
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**stunning Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Situated On An Over Half Acre Lot Overlooking The 12th Fairway Of The Interior, Heron Golf Course. With Its Delightful Curb Appeal And Manicured Landscape, Thi...

Image 10: A4695145

75 Osprey Point Drive, OSPREY, FL - $1,595,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,001 SQFT
  • 63 DOM
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Offered At A Price Approaching The Value Of The Two Buildable Lots Alone, This Architect-designed Estate Represents One Of The Most Compelling Opportunities Currently Available In The Oaks. Nestled Beneath Majestic Oak Trees And Surrounded By E...

Image 11: A4695429

206 Four Knot Lane, OSPREY, FL - $1,790,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,411 SQFT
  • 50 DOM
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Offering 3 Bedrooms, 2 Baths, Den/office, 2,411 Square Feet Under Air, A Spacious Living Room, A 2-car Garage, And A Private 14' X 37' Heated Pool Centrally Positioned As The Focal Point Of The Home. This Beautifully Updated, Move-in-ready Residen...

Image 12: A4698153

916 Macewen Drive, OSPREY, FL - $1,900,000

Residential, Single Family Residence
  • 5 Beds
  • 8 Baths
  • 5,986 SQFT
  • 21 DOM
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Virtually Staged. A Rare Canvas Of Luxury, Positioned On A Lush Double Lot Within The Sought-after, Gated Community Of The Oaks, In Osprey, Adjacent To Stunning Sarasota, Known For The Arts. Bordering The Heron Course On The Eighth Fairway, This ...

Image 13: A4669491

538 Dove Pointe Drive, OSPREY, FL - $1,950,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 4,346 SQFT
  • 279 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...

97 Sugar Mill Drive, OSPREY, FL - $1,950,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,885 SQFT
  • 104 DOM
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Welcome To An Exceptional Estate In The Oaks Bayside, Where Timeless Elegance Meets Modern Luxury In One Of Sarasota County’s Most Prestigious Gated Communities. Perfectly Positioned On A Private, Lush Homesite Beneath A Canopy Of Majestic Oaks, T...

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Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

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

Listing information last updated on August 14th, 2026 at 10:07pm EDT.