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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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Photo of Listing #A4185393

411 N Casey Key Rd, Osprey, FL - $6,499,000

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

Casey Key

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Price Reduced-1.5m-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...

Photo of Listing #A4408082

916 N Casey Key Rd, Osprey, FL - $5,950,000

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

Casey Key

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Location, Location, Location! New Price Over The Bridge To The North End Of The Beachfront Escape Of Casey Key You Arrive At The Tropical Oasis Of This 3 Residence Estate W/gulf Of Mexico & Bay Views. Once On The Property You Are Amazed By The Tr...

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

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,973 SQFT
  • 181 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 ...

Photo of Listing #A4425715

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

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 4,096 SQFT
  • 117 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...

854 N Casey Key Rd, Osprey, FL - $3,950,000

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

Casey Key

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Check Out The 3d Imaging Video! 1.5 Acre Gulf-to-bay Priced To Sell On Exclusive North End Casey Key. The Private Beach With No Public Access Is A Luxury Of Privacy That Few Places Offer & Is Part Of The Magic Of Casey Key. Majestic Sprawling Old...

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,202 SQFT
  • 38 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...

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

Residential, Single Family Home
  • 5 Beds
  • 3 Baths
  • 3,086 SQFT
  • 811 DOM

Casey Key

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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
  • 1,405 DOM

Casey Key

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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...

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

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,781 SQFT
  • 86 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 #N6104751

1224 N Casey Key Rd, Osprey, FL - $2,999,999

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 3,427 SQFT
  • 389 DOM

Palmer

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Priced To Sell In Mega Mansion Neighborhood. Great Opportunity To Get Over An Acre Of Gulf-to-bay On The Private Road Section Of The Exclusive North End Of Casey Key Where The Individual Properties Own The Beach. So You May Have Your Dogs On The B...

Photo of Listing #A4408555

410 N Casey Key Rd, Osprey, FL - $2,995,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,006 SQFT
  • 311 DOM

Casey Key

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Stunning Residence Nestled On An Oversized, Sub-dividable 1.45-acre Lot Along The Shores Of Little Sarasota Bay, Located In The Exclusive Residential Barrier Island Of Casey Key. This Amazing Property May Be Sub-divided, And Another Residence Can ...

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

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 6,461 SQFT
  • 171 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...

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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 May 26th, 2019 at 3:45pm EDT.