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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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814 N Casey Key Rd, Osprey, FL - $7,900,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 6,552 SQFT
  • 39 DOM

Casey Key

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Throughout His Illustrious Career, Gold Medal Winner From The American Institute Of Architects, Guy Peterson, Believes In Essentialism – A Concept That Demands Design By Analysis And Reduction, Rather Than Stylistic Imitation And Embellishment. Pe...

Photo of Listing #A4185393

411 N Casey Key Rd, Osprey, FL - $5,499,000

Residential, Single Family Home
  • 9 Beds
  • 11 Baths
  • 9,127 SQFT
  • 899 DOM

Casey Key

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Compelling Price Reduced Another 1m. Three Gulf Front Lots + Two Residences. Live Like A Midcentury Hollywood Starlet Transported To The Modern Era In A Stunning Seaside One-of-a-kind Estate With A Cobalt, Turquoise And Deep Blue Horizon. This Cov...

1044 N Casey Key Rd, Osprey, FL - $5,495,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 6,829 SQFT
  • 136 DOM

Casey Key Association

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Laffin Place… A Gated Bayfront Estate On 1.2 Acres On The Private North End Of Casey Key With Deeded Access To A Private Beach To Enjoy Spectacular Sunsets. The Property With Main House, Guest House & Bunk Room, Both With Separate Baths Offers Nea...

Photo of Listing #A4408082

916 N Casey Key Rd, Osprey, FL - $5,250,000

Residential, Single Family Home
  • 6 Beds
  • 6 Baths
  • 5,318 SQFT
  • 465 DOM

Casey Key

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New Price! Location, Location, Location! Arrive By Boat Or Car. North Casey Key Beachfront Tropical Oasis. 200ft Of Private Beach On The Gulf, 2 Homes On The Beach, Main Home On The Bay W/dock & Lift. Once On The Estate You Are Amazed By The Matur...

112 Osprey Point Dr, Osprey, FL - $4,450,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 327 DOM

Oaks

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Most Desirable Location In The Oaks Bayside Country Club; Truly A Boater's Dream! Featuring Your Own Private Dock With 3 Power Lifts..12,000/16,000. Driving Thru This Private Gated Community You Are Surrounded By A Canopy Of Mature Oak Trees. The ...

1208 N Casey Key Rd, Osprey, FL - $3,825,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,202 SQFT
  • 184 DOM

Casey Key

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Experience All The Warmth And Charm That This 1950 “old Florida” Beach House Has To Offer On Exclusive North Casey Key. Rarely Do You Find Privacy And Exquisite Walking Beach In Tandem. Set On Beautiful Oak Studded Grounds Spanning 100 Feet Of Pri...

Photo of Listing #A4425715

121 N Casey Key Rd, Osprey, FL - $3,800,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,096 SQFT
  • 263 DOM

Casey Key

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Privacy Abounds Behind The Gated Entry To This Unique Spanish Mediterranean Beachfront Home Hidden Away In Tropical Splendor On The Sparkling Blue Waters Of The Gulf Of Mexico. Attention To Detail Is Not Lacking In This Gorgeous 4 Bedroom 5 1/2 Ba...

Photo of Listing #N6101230

854 N Casey Key Rd, Osprey, FL - $3,390,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,462 SQFT
  • 460 DOM

Casey Key

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Reduced 1.5 Acre Gulf-to-bay Priced To Sell On Exclusive North End Casey Key. Majestic Sprawling Old Oaks & Cedar Trees Giving It An Unspoiled "old Florida" Feeling. The Private Beach With No Public Access Is A Luxury Of Privacy That Few Places O...

1042 N Casey Key Rd, Osprey, FL - $3,275,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,781 SQFT
  • 232 DOM

Palmer

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Open Your Blinds Each Morning And Say To Yourself," Good Morning Beautiful"! This Majestic Residence On The Sarasota Bay Offers Expansive Bay Views, Lush Tropical Landscape And Exclusive Deeded Beach Access On The Treasured North End Of Casey Key....

Photo of Listing #A4443284

931 Blue Heron Overlook, Osprey, FL - $3,000,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 6,977 SQFT

Oaks

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The Oaks, This Distinguished Residence Is Sited At The End Of A Cul-de-sac Boasting Breathtaking Views Stretching All The Way To The Oaks Clubhouse And Strategically Located On The New Fry/straka (course Architects Of Erin Hill, Site Of The 2017 U...

136 Osprey Point Dr, Osprey, FL - $2,790,000

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 6,461 SQFT
  • 317 DOM

Oaks

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Opportunity Of A Life Time! This Magnificent Three-level Mansion Is Located In The Exclusive Private Gated Community Oaks Bayside. This Home Is Priced To Sell And Is Below Market And Replacement Value. Exquisite Brazillan Cherry Wood Flooring Thro...

285 Sugar Mill Dr, Osprey, FL - $1,695,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,578 SQFT
  • 71 DOM

Oaks

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Escape To Paradise. Located In The Waterfront Community Of Oaks Bayside, This One-of-a-kind Walled And Gated Estate Is A Private Oasis Perfect For Entertaining Guests Or For Multi-generational Living. The Expansive Open Pool And Patio Area Is Posi...

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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 DBA Stellar MLS.

Listing information last updated on October 19th, 2019 at 9:00pm EDT.