Osprey, FL Homes

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  /2

  Est $775,330

  Not Listed For Sale

  424 Cezanne Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 2,945 Sq Ft
  • Built 1975

  424 Cezanne Dr, Osprey, FL 34229

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY
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  /31

  $695,000

  • Land
  • 25,700 Sq Ft
  • $1,177,966 per Acre

  216 Osprey Point Dr, Osprey, FL 34229

  One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  216 Osprey Point Dr, Osprey, FL 34229
• 

  

  /2

  $2,300,000

  Sold Apr 06, 2026

  896 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $473/SF
  • 35 Days On Market

  Current Estimated Value $2,277,620

  Last Listing Agent Marisa Marino BRIGHT REALTY

  896 MacEwen Dr, Osprey, FL 34229
• 

  

  /2

  Est $422,333

  Not Listed For Sale

  441 N Shore Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft
  • Built 1970

  441 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Dawn Barnett EXIT KING REALTY
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  /47

  $3,295,000

  • 3 Beds
  • 4.5 Baths
  • 2,572 Sq Ft

  135 Tina Island Dr, Osprey, FL 34229

  **EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid

  Mark Lyda GENEROUS PROPERTY

  135 Tina Island Dr, Osprey, FL 34229
• 

  /2

  $2,315,000

  Sold Oct 30, 2025

  112 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 8,635 Sq Ft
  • Built 1989

  Last Sold Summary

  • 41% Below List Price
  • $268/SF
  • 156 Days On Market

  Current Estimated Value $3,086,350

  Last Listing Agent Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  Est $1,011,181

  Not Listed For Sale

  434 N Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,932 Sq Ft
  • Built 1989

  434 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 254 Days On Market

  Last Listing Agent Victoria Stultz ENGEL + VOELKERS SARASOTA
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  /51

  $700,000

  $27K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  759 Fordingbridge Way, Osprey, FL 34229

  Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a

  Steven Koleno BEYCOME OF FLORIDA LLC

  759 Fordingbridge Way, Osprey, FL 34229
• 

  /2

  $665,000

  Sold Nov 06, 2025

  563 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,346 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 5 Days On Market

  Current Estimated Value $661,409

  Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  563 Pine Ranch Rd E, Osprey, FL 34229
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  /29

  Est $2,161,524

  Not Listed For Sale

  162 Puesta Del Sol, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 4,747 Sq Ft
  • Built 2003

  162 Puesta Del Sol, Osprey, FL 34229

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Drew Russell MICHAEL SAUNDERS & COMPANY
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  /83

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 3,771 Sq Ft

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  Virtually Staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County.Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water

  Angelic Tassos CORCORAN DWELLINGS REALTY

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
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  /2

  $1,500,000

  Sold Sep 19, 2025

  462 E MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,611 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $574/SF
  • 29 Days On Market

  Current Estimated Value $1,470,447

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  462 E MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $702,866

  Not Listed For Sale

  1192 Mallard Marsh Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,695 Sq Ft
  • Built 2002

  1192 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 191 Days On Market

  Last Listing Agent Marie Fogarty M H FOGARTY AND COMPANY LLC
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  /16

  $1,350,000

  $50K PRICE DROP

  • Land
  • 2.51 Acres
  • $537,849 per Acre

  2099 S Tamiami Trail, Osprey, FL 34229

  NEW PRICE! Location! Location! This 2.51 Acre Lot is available for sale directly on South Tamiami Trail in Osprey - where Sarasota is growing and expanding! This property is zoned OPI and would be a good fit for a dental, veterinary, medical center or business offices with potential residential above. Great exposure with consistently heavy traffic from Sarasota to Naples on S. Tamiami Trail just

  Susan Repp COLDWELL BANKER REALTY

  2099 S Tamiami Trail, Osprey, FL 34229
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  /2

  $166,000

  Sold May 21, 2026

  238 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $144/SF
  • 15 Days On Market

  Last Listing Agent Susan Retzke RE/MAX PALM

  238 Palm Air Dr, Osprey, FL 34229
• 

  /2

  Est $555,327

  Not Listed For Sale

  685 Clear Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2002

  685 Clear Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Brian ODonnell,PLLC REALTY BY DESIGN LLC
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  /91

  $459,900

  $215K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  401 N Point Rd Unit 301, Osprey, FL 34229

  Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
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  /66

  $654,000

  Sold Apr 16, 2026

  1303 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $339/SF
  • 93 Days On Market

  Current Estimated Value $643,235

  Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, Osprey, FL 34229
• 

  /2

  Est $877,564

  Not Listed For Sale

  1200 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 2002

  1200 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 118 Days On Market

  Last Listing Agent Sharon Osborne, PA COLDWELL BANKER SARASOTA CENT.
• 

  

  /95

  $525,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3621 N Point Rd Unit 301, Osprey, FL 34229

  Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut

  Steve Abbe COLDWELL BANKER REALTY

  3621 N Point Rd Unit 301, Osprey, FL 34229
• 

  /2

  $241,000

  Sold May 28, 2026

  0 Sarabay Rd, Osprey, FL 34229

  • Land
  • 13,939 Sq Ft
  • $753,125 per Acre

  Last Sold Summary

  • 7% Above List Price
  • 3 Days On Market

  Last Listing Agent Cheri Castro MICHAEL SAUNDERS & COMPANY

  0 Sarabay Rd, Osprey, FL 34229
• 

  /2

  Est $803,938

  Not Listed For Sale

  1030 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,433 Sq Ft
  • Built 2003

  1030 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Kimberly Young BERKSHIRE HATHAWAY HOMESERVICE
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  /58

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229

  Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West.

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229
• 

  /2

  $925,000

  Sold Jul 15, 2026

  1602 Southbay Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,980 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $310/SF
  • 198 Days On Market

  Current Estimated Value $1,012,115

  Last Listing Agent Thomas Kiessling COMPASS FLORIDA LLC

  1602 Southbay Dr, Osprey, FL 34229
• 

  /2

  Est $653,155

  Not Listed For Sale

  1109 Scherer Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • Built 2002

  1109 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /48

  $599,000

  $86K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
• 

  /2

  $520,000

  Sold Jun 17, 2026

  1337 Copperwood Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 199 Days On Market

  Current Estimated Value $536,886

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
• 

  /2

  Est $262,569

  Not Listed For Sale

  234 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1979

  234 Patterson Ave, Osprey, FL 34229

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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  /3

  $34,900

  • 1 Bed
  • 1 Bath
  • 418 Sq Ft

  124 Happy Haven Dr Unit 56, Osprey, FL 34229

  Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 418 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 56, Osprey, FL 34229
• 

  /2

  $570,000

  Sold Apr 03, 2026

  51 Webb St, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 6 Days On Market

  Current Estimated Value $572,485

  Last Listing Agent Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
• 

  /2

  Est $565,169

  Not Listed For Sale

  825 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,229 Sq Ft
  • Built 1996

  825 Oak Pond Dr, Osprey, FL 34229

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Magda Cetta Whelton DOUGLAS ELLIMAN
• 

  

  /85

  $497,000

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229

  West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass

  Christine Pope MICHAEL SAUNDERS & COMPANY

  2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229
• 

  /2

  $1,700,000

  Sold Sep 18, 2025

  898 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 4,132 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $411/SF
  • 0 Days On Market

  Current Estimated Value $1,796,770

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  898 MacEwen Dr, Osprey, FL 34229
• 

  

  /48

  Est $590,891

  Not Listed For Sale

  522 Meadow Sweet Cir, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,424 Sq Ft
  • Built 1998

  522 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 145 Days On Market

  Last Listing Agent Sandi Tresh RE/MAX PALM REALTY OF VENICE
• 

  

  /38

  $899,995

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft

  14021 Bellagio Way Unit 309, Osprey, FL 34229

  Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy

  Tristin Hopler COMPASS FLORIDA, LLC

  14021 Bellagio Way Unit 309, Osprey, FL 34229
• 

  /2

  $329,000

  Sold Jan 14, 2026

  85 Navigation Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $230/SF
  • 8 Days On Market

  Current Estimated Value $317,399

  Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
• 

  /2

  Est $780,468

  Not Listed For Sale

  790 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 2002

  790 Shadow Bay Way, Osprey, FL 34229

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  

  /54

  $795,000

  $85K PRICE DROP Under Contract

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  401 N Point Rd Unit 504, Osprey, FL 34229

  Under contract-accepting backup offers. INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a

  Lenore Treiman MICHAEL SAUNDERS & COMPANY

  401 N Point Rd Unit 504, Osprey, FL 34229
• 

  /2

  $155,000

  Sold Nov 26, 2025

  170 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $162/SF
  • 132 Days On Market

  Last Listing Agent Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
• 

  /2

  Est $232,600

  Not Listed For Sale

  225 Woodland Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  225 Woodland Dr, Osprey, FL 34229

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

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