Dashboard

Dashboard

Login using...

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.

If you want more detailed information about a listing, just click on the VIEW DETAILS action button. Here you will find detail information about the property, including additional photos and virtual tours, when available. If you like what you see and want to come back to it easily, just click on the BOOKMARK button to save it to your favorites.

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
Map Save this Search
Sort listings by:Price, Highest First
Photo of Listing #A4185393

411 N Casey Key Rd, Osprey, FL - $7,995,000

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

Casey Key

View details More Photos Save

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 #A4408082

916 N Casey Key Rd, Osprey, FL - $6,250,000

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

Casey Key

View details More Photos Save

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...

1044 N Casey Key Rd, Osprey, FL - $6,200,000

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

Casey Key Association

View details More Photos Save

Located On North Casey Key Along The Sparkling Waters Of Sarasota Bay, A Very Private Dream Estate Known As Laffin Place Is Perfectly Nestled On 1.2 Acres Of Luxuriant Landscaping. Built In 1937, It Is One Of The Few Original Island Homes Still In...

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

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

Oaks

View details More Photos Save

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 ...

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

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

Casey Key

View details More Photos Save

A Great Value Priced To Sell On Exclusive North End Casey Key. Rarely Available 1.5 Acre Gulf-to-bay Parcel With Conservation Easement On The Gulf Side. The Private Beach With No Public Access For Miles Is A Luxury Of Privacy That Few Places Offer...

Photo of Listing #U7850966

1224 N Casey Key Rd, Osprey, FL - $3,500,000

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

Palmer

View details More Photos Save

1 Acre N Casey Key, Gulf To Bay, Private Road, Beach + Dock, 5 Brooms, 4 Bath, 50's Ranch, Rehab Or Tear Down, Offered As-is.

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

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

Casey Key

View details More Photos Save

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
  • 1,276 DOM

Casey Key

View details More Photos Save

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...

1027 N Casey Key Rd, Osprey, FL - $2,995,000

Residential, Single Family Home
  • 4 Beds
  • 3 Baths
  • 2,990 SQFT
  • 72 DOM

Casey Key

View details More Photos Save

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...

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
  • 182 DOM

Casey Key

View details More Photos Save

Stunning Residence Nestled On An Oversized 1.45-acre Lot Along The Shores Of Little Sarasota Bay, Located In The Exclusive Residential Barrier Island Of Casey Key. Deeded Beach Access To The Gulf Of Mexico And Two Docks For Many Vessel Types Allow...

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

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

Oaks

View details More Photos Save

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...

Photo of Listing #A4208052

91 Osprey Point Dr, Osprey, FL - $1,995,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,100 SQFT
  • 356 DOM

Oaks

View details More Photos Save

Iconic Architecture In Sarasota’s Premiere Golf And Country Club. This Magnificent 4-bedroom Estate Was Designed And Built By Bo Macewen And Brims With The Essence Of Warm, Southern Hospitality. Bo Was The Original Architect For The Oaks And He Cr...

Return to Communities Search

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 January 18th, 2019 at 5:31pm EST.