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Osprey Homes for Sale

Osprey is a small town in Sarasota County, located just below the southern fringe of Sarasota. In Osprey, you’ll find The Oaks – one of our area’s finest member-owned Country Clubs. Osprey is also home to Oscar Scherer State Park where you’ll find opportunities for hiking, bicycling, and wildlife viewing. Canoeists and kayakers can paddle along South Creek, a blackwater stream that flows to the Gulf of Mexico.

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View Osprey condos for sale or see below for homes for sale in Osprey

Osprey Homes

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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1160 N Casey Key Rd, Osprey, FL - $14,500,000

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 10.1k SQFT
  • 690 DOM
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Welcome To Eventide. This Gated, Impeccably Designed Estate, Privately Positioned On The Treasured N. End Of Casey Key, Sweeps From A Sandy Walking Beach On The Gulf Of Mexico To A Protected Yachting Lagoon On Blackburn Bay. Composed Of Over 10,0...

411 N Casey Key Rd, Osprey, FL - $8,900,000

Residential, Single Family Home
  • 9 Beds
  • 11 Baths
  • 9,127 SQFT
  • 212 DOM
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Live Like A Midcentury Hollywood Starlet Transported To The Modern Era In A Stunning Seaside One-of-a-kind Estate. This Coveted North Casey Key, 300-foot Gulf Of Mexico Frontage Property Consists Of Two Remarkable Homes Of 4,000 And 5,000 Square F...

Photo of Listing #A4203031

230 N Casey Key Rd, Osprey, FL - $5,500,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 3,311 SQFT
  • 5 DOM
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Welcome! You’ve Just Arrived At Your Private Island Paradise. This Is Luxury In A Setting That’s Just About As Exclusive As It Gets. Almost 3 Acres, This Estate Size Casey Key Waterfront Property Is Nature’s Gulf To Bay Paradise. Prime Land, In T...

Photo of Listing #A4203910

222 N Casey Key Rd, Osprey, FL - $4,500,000

Land, Single Family Use
  • 4 DOM
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Look No Further, Your Private Oasis Is Waiting For You. There Are Endless Possibilities On This Beach-to-bay Double Lot. This Magnificent Property, Which Has Over 200 Ft Of Gulf And Bay Frontage And Is More Than 525 Ft Deep, Is A Unique Opportunit...

144 N Casey Key Rd, Osprey, FL - $4,499,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,397 SQFT
  • 548 DOM
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Villa Dei Sogni (house Of Dreams) Presents An Architectural Masterpiece Framed By Finely Crafted Limestone Columns And Details Throughout The Exterior/interior Created By Artisans Around The World. As You Approach The Residence From The Walkway Th...

Photo of Listing #A4107068

532 N Casey Key Rd, Osprey, FL - $3,999,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,024 SQFT
  • 935 DOM
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Villa Crescendo Is The Epitome Of Harmony Blending The Views And Sounds Of The Beach And Bay Waters From Every Room. Casey Means A Proclamation Of Peace That Truly Defines Exclusive Casey Key. If You Are Looking For Tranquility, Privacy And A Qual...

50 W Bay St, Osprey, FL - $3,680,000

Residential, Single Family Home
  • 7 Beds
  • 7 Baths
  • 6,659 SQFT
  • 126 DOM
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Discover A Once-in-a-lifetime Opportunity To Restore, Build, Or Develop On 3.68 Acres Directly On Sarasota Bay In Scenic, Historic Osprey Just South Of The Oaks. Dating Back To The Late 1800's And Known As One Of The First Properties To Be Settled...

332 N Casey Key Rd, Osprey, FL - $3,590,000

Land, Single Family Use
  • 962 DOM
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If You Have Dreamed Of Life By The Shore, Here Is Your Opportunity To Own Two Secluded Acres On The Majestic Barrier Island Of Casey Key. Stretching From The Azure Waters Of The Gulf Of Mexico To The Fabulous Boating Water Of The Intracoastal, Thi...

420 N Casey Key Rd, Osprey, FL - $3,499,000

Residential, Single Family Home
  • 5 Beds
  • 9 Baths
  • 6,846 SQFT
  • 49 DOM
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Rebuilt In 2006, This Classic Coastal Home Is Sited On 100 Feet Of Bayfront With Deeded Beach Access. The Main Home Is Protected With Impact Glass Andersen Windows And Doors, Automated Hurricane Shutters, A Safe Room, Elevator And A Whole House Ge...

608 N Casey Key Rd, Osprey, FL - $3,450,000

Residential, Single Family Home
  • 5 Beds
  • 3 Baths
  • 3,086 SQFT
  • 270 DOM
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This Prime 1.5 Acre Property Has 175 Ft. Of Gulf Front And 175 Ft. Of Little Sarasota Bay Front And Is More Than 450 Ft. Deep. Secluded By Mature Oaks, Palms, Pines, Agave And An Enormous Banyan Tree, The Rustic Residence Has Changed Little Since...

Photo of Listing #A4127758

608 N Casey Key Rd, Osprey, FL - $3,450,000

Land, Single Family Use
  • 864 DOM
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North Casey Key - Home To Celebrities And Fortune 500 Executives - Is Considered The Most Exclusive And Private Stretch Of Land On Casey Key, A Pristine 8 Mile Long Barrier Island Located Between Sarasota And Venice. This Prime 1.5 Acre Property I...

Photo of Listing #A4179929

1027 N Casey Key Rd, Osprey, FL - $3,250,000

Residential, Single Family Home
  • 4 Beds
  • 3 Baths
  • 2,990 SQFT
  • 270 DOM
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Cross Over A Historic Swing Bridge Into The Serenity Of Private North Casey Key. Here, In This Tranquil Community Nestled Along A Winding Island Road, Is A Rare Opportunity To Own A Slice Of Paradise Not On The Market For 40 Years. The Custom-buil...

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

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.

Listing information last updated on December 16th, 2017 at 2:03am EST.