Osprey, FL Homes

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  $285,000

  Sold May 22, 2026

  4173 Frontier Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Below List Price
  • $251/SF
  • 3 Days On Market

  Current Estimated Value $288,687

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

  4173 Frontier Ln, Osprey, FL 34229
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  /2

  Est $539,138

  Not Listed For Sale

  590 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 1999

  590 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 53 Days On Market
• 

  

  

  /77

  $1,175,000

  $114K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  14021 Bellagio Way Unit 404, Osprey, FL 34229

  This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new

  Megan George PREMIER SOTHEBYS INTL REALTY

  14021 Bellagio Way Unit 404, Osprey, FL 34229
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  /2

  $470,000

  Sold Feb 10, 2026

  1363 New Forest Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 2002

  Last Sold Summary

  • 14% Below List Price
  • $270/SF
  • 260 Days On Market

  Current Estimated Value $475,114

  Last Listing Agent Pamela Strom RE/MAX PALM

  1363 New Forest Ln, Osprey, FL 34229
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  /2

  Est $431,601

  Not Listed For Sale

  329 Bay Vista Ave, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1963

  329 Bay Vista Ave, Osprey, FL 34229

  Last Sold Summary

  • 244 Days On Market
• 

  

  /92

  $795,000

  $505K PRICE DROP Pending

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

  393 N Point Rd Unit 604, Osprey, FL 34229

  Under contract-accepting backup offers. Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  /2

  $649,000

  Sold Aug 26, 2025

  0 Four Knot Ln, Osprey, FL 34229

  • Land
  • 11,325 Sq Ft
  • $2,496,154 per Acre

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Gregory Wood CERUS REALTY

  0 Four Knot Ln, Osprey, FL 34229
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  /2

  Est $421,284

  Not Listed For Sale

  418 Sarabay Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft
  • Built 1960

  418 Sarabay Rd, Osprey, FL 34229

  Last Sold Summary

  • 81 Days On Market
• 

  /2

  $540,749

  New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 302, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 302, Osprey, FL 34229
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  /2

  $43,000

  Sold Nov 04, 2025

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • 98 Days On Market

  Last Listing Agent Rick Bumbaca NORTHGROUP REAL ESTATE, INC

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229
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  /2

  Est $747,141

  Not Listed For Sale

  356 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,369 Sq Ft
  • Built 1990

  356 S Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 36 Days On Market
• 

  

  /88

  $2,700,000

  $200K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly positioned on the 1st hole of the Heron Course, capturing sweeping golf course and clubhouse views—just minutes from Siesta Beach and Casey Key. The main residence offers 4,700+ square feet, complemented by a private 1,500+ square

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /2

  $215,000

  Sold May 01, 2026

  362 Pine Run Dr Unit 362, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1973

  Last Sold Summary

  • $176/SF

  Current Estimated Value $230,952

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  362 Pine Run Dr Unit 362, Osprey, FL 34229
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  /81

  Est $1,144,579

  Not Listed For Sale

  385 N Point Rd Unit 604, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  385 N Point Rd Unit 604, Osprey, FL 34229

  Last Sold Summary

  • 48 Days On Market
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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
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  /2

  $565,000

  Sold Apr 03, 2026

  767 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,162 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $261/SF
  • 30 Days On Market

  Current Estimated Value $572,506

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  767 Fordingbridge Way, Osprey, FL 34229
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  /21

  Est $1,078,574

  Not Listed For Sale

  1108 Bayhead Ln, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,541 Sq Ft
  • Built 1997

  1108 Bayhead Ln, Osprey, FL 34229

  Last Sold Summary

  • 99 Days On Market
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  $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
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  $2,500,000

  Sold Jun 02, 2026

  409 N Point Rd Unit 1001, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Below List Price
  • $825/SF
  • 0 Days On Market

  Current Estimated Value $2,361,123

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 1001, Osprey, FL 34229
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  /2

  Est $248,894

  Not Listed For Sale

  707 Pine Run Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  707 Pine Run Dr, Osprey, FL 34229

  Last Sold Summary

  • 134 Days On Market
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  /49

  $599,000

  Pending

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

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229

  Under contract-accepting backup offers. Welcome home! This GULF ACCESS, WATERFRONT condo w/ AVAILABLE BOAT SLIPS BEHIND THE UNIT, in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A

  Mackenzie Davis-Mahan DOWNING FRYE REALTY, INC.

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229
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  /2

  $445,000

  Sold Apr 10, 2026

  288 Woods Point Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 1991

  Last Sold Summary

  • $249/SF
  • 4 Days On Market

  Current Estimated Value $441,840

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  288 Woods Point Rd, Osprey, FL 34229
• 

  

  /22

  Est $540,721

  Not Listed For Sale

  743 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 2000

  743 Anna Hope Ln, Osprey, FL 34229

  Last Sold Summary

  • 177 Days On Market
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  /51

  $749,000

  $22K PRICE INCREASE

  • 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
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  /2

  $220,000

  Sold Oct 23, 2025

  216 Woodland Dr Unit 216, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $166/SF
  • 55 Days On Market

  Current Estimated Value $216,249

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  216 Woodland Dr Unit 216, Osprey, FL 34229
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  /2

  Est $1,723,327

  Not Listed For Sale

  165 Sugar Mill Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,912 Sq Ft
  • Built 1989

  165 Sugar Mill Dr, Osprey, FL 34229

  Last Sold Summary

  • 152 Days On Market
• 

  

  /60

  $579,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  1367 Thornapple Dr, Osprey, FL 34229

  Discover unparalleled luxury in this exquisite Lee Wetherington-built residence, ideally in Willowbend within Osprey. A grand entry hall with high-end finishes, tray ceilings and rich crown molding welcomes you to a home meticulously perfected by discerning sellers. This ideally positioned home boasts a 1⁄4+ acre homesite with an expansive front yard, a roomy side-entry paver newly sealed

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1367 Thornapple Dr, Osprey, FL 34229
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  /2

  $660,000

  Sold Mar 10, 2026

  471 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,267 Sq Ft
  • Built 2001

  Last Sold Summary

  • 12% Below List Price
  • $291/SF
  • 197 Days On Market

  Current Estimated Value $657,410

  Last Listing Agent Bill Cantrell WILLIAM RAVEIS - FLORIDA LLC

  471 Park Trace Blvd, Osprey, FL 34229
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  /78

  Est $726,270

  Not Listed For Sale

  522 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft
  • Built 2003

  522 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 48 Days On Market
• 

  

  /83

  $850,000

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

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  One or more photo(s) has been 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,

  Angelic Tassos CORCORAN DWELLINGS REALTY

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

  $1,015,000

  Sold Aug 01, 2025

  678 Clear Creek Dr, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 3,912 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $259/SF
  • 11 Days On Market

  Current Estimated Value $978,387

  Last Listing Agent Dena Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /2

  Est $698,246

  Not Listed For Sale

  520 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft
  • Built 2003

  520 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 4 Days On Market
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  /16

  $1,400,000

  • Land
  • 2.51 Acres
  • $557,769 per Acre

  2099 S Tamiami Trail, Osprey, FL 34229

  2.51 Acre Lot 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 an office/medical center or retail with residential above. Great exposure with consistently heavy traffic from Sarasota to Ft. Myers on S. Tamiami Trail just minutes from Sarasota Bay, Oscar Scherer State Park, Legacy Trail and all that Sarasota

  Susan Repp COLDWELL BANKER REALTY

  2099 S Tamiami Trail, Osprey, FL 34229
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  /2

  $560,000

  Sold Apr 10, 2026

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2001

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 147 Days On Market

  Current Estimated Value $589,611

  Last Listing Agent Per Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229
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  /41

  Est $666,919

  Not Listed For Sale

  675 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 2003

  675 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 37 Days On Market
• 

  

  /91

  $475,000

  $200K 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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  /2

  $1,200,000

  Sold Oct 24, 2025

  1484 Seafarer Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,479 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $345/SF
  • 82 Days On Market

  Current Estimated Value $1,186,193

  Last Listing Agent Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
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  /40

  Est $1,115,630

  Not Listed For Sale

  109 Tina Island Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,827 Sq Ft
  • Built 1988

  109 Tina Island Dr, Osprey, FL 34229

  Last Sold Summary

  • 15 Days On Market
• 

  

  /95

  $625,000

  • 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
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  /2

  $1,275,000

  Sold Sep 30, 2025

  364 Renoir Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,241 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $393/SF
  • 7 Days On Market

  Current Estimated Value $1,290,719

  Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229

Showing Results 401 - 440, Page 11 of 18