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Osprey Florida Real Estate Listings

Osprey, Florida is a historic city on Florida’s southwest coast. Osprey is a diverse community featuring multi-million dollar homes among the intercostal highway. 

Browse Osprey Real Estate

View all real estate for sale in Osprey, Florida below with RoseBay International, Inc. Contact us if you have questions or would like to schedule a showing. 

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411 Casey Key Road, Osprey, FL 34229

Price$8,299,000

Est. Mortgage: $/month

MLS Number A4185393

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 411 N Casey Key Road
  • Square Feet 9,127
  • Year Built 1977

Listed by PREMIER SOTHEBY'S INTL. REALTY

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Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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916 Casey Key Road, Osprey, FL 34229

Price$7,975,000

Est. Mortgage: $/month

MLS Number A4408082

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 916 N Casey Key Road
  • Square Feet 5,318
  • Year Built 1973

Listed by COLDWELL BANKER RES R E

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1232 Casey Key Road, Osprey, FL 34229

Price$6,895,000

Est. Mortgage: $/month

MLS Number A4209805

  • Single Family Residential
  • Area 34229 - Osprey
  • Square Feet 8,121
  • Year Built 2005
  • Parking Spaces 4

Listed by MICHAEL SAUNDERS & COMPANY

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1044 Casey Key Road, Osprey, FL 34229

Price$6,200,000

Est. Mortgage: $/month

MLS Number A4207422

  • Single Family Residential
  • Area 34229 - Osprey
  • Square Feet 6,829
  • Year Built 1937
  • Parking Spaces 3

Listed by RE/MAX ALLIANCE GROUP

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

230 Casey Key Road, Osprey, FL 34229

Price$5,500,000

Est. Mortgage: $/month

MLS Number A4203031

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 230 N Casey Key Road
  • Square Feet 3,311
  • Year Built 1951

Listed by COLDWELL BANKER RES R E

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

144 Casey Key Road, Osprey, FL 34229

Price$4,395,000

Est. Mortgage: $/month

MLS Number A4190275

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 144 N Casey Key Road
  • Square Feet 5,397
  • Year Built 2003

Listed by MICHAEL SAUNDERS & COMPANY

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

238 Casey Key Road, Osprey, FL 34229

Price$3,950,000

Est. Mortgage: $/month

MLS Number A4203910

  • Land
  • Co Listing Office Id 231502433
  • Subdivision Acreage & Unrec
  • High School Venice Senior High
  • Acreage 2

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 opportunity in the most exclusive end of North Casey Key to build your dream home or compound. Beautiful and unspoiled, with private beachfront on one end, a pristine and quiet bay on the other, as well as a with a private lagoon and nature trail, makes the perfect recipe for this exceptional lot to be developed to its fullest potential. Only a few select waterfront properties exist. North Casey Key employs an owner roaming security Guard and is home to Fortune 500 executives. These 2 separate buildable lots have individual parcel numbers. Properties can be purchased with MLS #A4203031 for a total of 5.17 acres of buildable land.

Listed by COLDWELL BANKER RES R E

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1224 Casey Key Road, Osprey, FL 34229

Price$3,700,000

Est. Mortgage: $/month

MLS Number U7850966

  • Single Family Residential
  • Area 34229 - Osprey
  • Square Feet 3,427
  • Year Built 1956
  • Bathroom 4

Listed by JACK KELLER INC

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

552 Eagle Watch Lane, Osprey, FL 34229

Price$3,685,000

Est. Mortgage: $/month

MLS Number A4214669

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 552 Eagle Watch Lane
  • Square Feet 6,300
  • Year Built 2018

Listed by BERKSHIRE HATHAWAY HOMESERVICE

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

50 Bay, Osprey, FL 34229

Price$3,680,000

Est. Mortgage: $/month

MLS Number A4158305

  • Land
  • Subdivision Saunders V A Resub
  • Acreage 3.68
  • Square Feet 160,358
  • Waterfront 1

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, this sweeping site captures a true sense of Old Florida, while offering exciting new possibilities. The options include the creation of a dream principal estate compound to restore the existing homes or to build new. Alternatively, a buyer can opt to develop an enclave of homes, with approval in place to build on 13 individual lots with boat docks already permitted for each site, as well as 10 acres of submerged land on this astounding waterfront location. Osprey, positioned between the world-class destinations of Sarasota and Venice, is the best of both worlds with a small town feeling with tree-lined streets that end with glimpses of Sarasota Bay, and is minutes from vibrant shops, restaurants, arts and culture of downtown Sarasota. This remarkable waterfront property invites you to become the next chapter of its history.

Listed by MICHAEL SAUNDERS & COMPANY

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

608 Casey Key Road, Osprey, FL 34229

Price$3,450,000

Est. Mortgage: $/month

MLS Number A4127758

  • Land
  • Subdivision Casey Key
  • High School Venice Senior High
  • Junior High Venice Area Middle
  • Acreage 1.5

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 is one of only a few Gulf to Bay properties on North Casey Key available for sale. It has 175 ft. of Gulf front and 175 ft. of Little Sarasota Bay front and is more than 450 ft. deep. Secluded behind the mature oaks, palms, pines, agave and an enormous banyan tree is one of the first homesteads built on the Island. Remnants of a dock that extends into Little Sarasota Bay are evidence of the romantic history of the 1916 residence. Unlikely to be salvaged, the Old Florida home, built of pecky cedar, served as lodging for adventurers and their guides who arrived by boat to hunt the lushly vegetated key. Perhaps the by-gone-era, the 10 ft. ceilings, hardwood floors, 4 fireplaces, original blown glass sconces, French doors and lunette windows will be the inspiration for the buyers new estate. Seller may consider some financing.

Listed by ROSEBAY INTERNATIONAL, INC

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

608 Casey Key Road, Osprey, FL 34229

Price$3,450,000

Est. Mortgage: $/month

MLS Number A4177105

  • Single Family Residential
  • Area 34229 - Osprey
  • Address 608 N Casey Key Road
  • Square Feet 3,086
  • Year Built 1916

Listed by ROSEBAY INTERNATIONAL, INC

{$office->Name}

Southside Village
1815 S Osprey Ave
Sarasota FL, 34239
Office: 941-366-7673

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Jul 12, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details