5,083

Osprey, FL Homes

Section Image
    • /68

      Est $850,707

      Not Listed For Sale

      1081 Scherer Way, Osprey, FL 34229

      • 6 Beds
      • 3 Baths
      • 3,982 Sq Ft
      • Built 2004
      1081 Scherer Way, Osprey, FL 34229

      Last Sold Summary

      • 76 Days On Market

  • /4

    $32,500

    570 Blackburn Point Rd Unit 38, Osprey, FL 34229

    Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Plus, HOA is prepaid thru the end of 2025! Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit 38, Osprey, FL 34229
  • /2

    $660,000

    Sold Aug 26, 2025

    463 Park Trace Blvd, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft
    • Built 2002

    Last Sold Summary

    • 12% Below List Price
    • $307/SF
    • 63 Days On Market

    Current Estimated Value $662,028

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

    463 Park Trace Blvd, Osprey, FL 34229
    • /2

      Est $688,990

      Not Listed For Sale

      521 Luminary Blvd, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,504 Sq Ft
      • Built 2004
      521 Luminary Blvd, Osprey, FL 34229

      Last Sold Summary

      • 69 Days On Market

  • /52

    $599,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft

    557 Crane Prairie Way, Osprey, FL 34229

    Under contract-accepting backup offers. Welcome to this impeccably maintained, MAINTENANCE FREE home in the highly desirable Willowbend community, with tranquil LAKEVIEWS, exceptional amenities and an unbeatable LOCATION. Built by renowned Lee Wetherington and lovingly maintained by its original owner, this quality-constructed residence features a spacious open split-bedroom floor plan with 3

    Lori Lockhart COLDWELL BANKER REALTY

    557 Crane Prairie Way, Osprey, FL 34229
  • /2

    $750,000

    Sold Dec 30, 2025

    523 Habitat Blvd, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,314 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $324/SF
    • 122 Days On Market

    Current Estimated Value $736,347

    Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    523 Habitat Blvd, Osprey, FL 34229
    • /2

      Est $2,554,049

      Not Listed For Sale

      388 Bunker Hill, Osprey, FL 34229

      • 5 Beds
      • 5.5 Baths
      • 4,937 Sq Ft
      • Built 1999
      388 Bunker Hill, Osprey, FL 34229

      Last Sold Summary

      • 64 Days On Market

  • /39

    $999,000

    $151K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,086 Sq Ft

    14041 Bellagio Way Unit 218, Osprey, FL 34229

    Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers a bright, light-filled living space with water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a 40' wet slip—($100,000 value) providing immediate access to boating, fishing, and the

    Kelli Eggen COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 218, Osprey, FL 34229
  • /2

    $799,000

    Sold Mar 09, 2026

    529 Habitat Blvd, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,617 Sq Ft
    • Built 2003

    Last Sold Summary

    • $305/SF
    • 2 Days On Market

    Current Estimated Value $794,908

    Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    529 Habitat Blvd, Osprey, FL 34229
    • /2

      Est $2,269,711

      Not Listed For Sale

      425 E MacEwen Dr, Osprey, FL 34229

      • 5 Beds
      • 5.5 Baths
      • 5,153 Sq Ft
      • Built 1999
      425 E MacEwen Dr, Osprey, FL 34229

      Last Sold Summary

      • 62 Days On Market

  • /42

    $829,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,876 Sq Ft

    1211 Lost Creek Ct, Osprey, FL 34229

    Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s

    Mark Lyda GENEROUS PROPERTY

    1211 Lost Creek Ct, Osprey, FL 34229
  • /2

    $550,000

    Sold Mar 23, 2026

    510 Latitude Ln, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,298 Sq Ft
    • Built 2004

    Last Sold Summary

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

    Current Estimated Value $561,865

    Last Listing Agent Marisa Marino BRIGHT REALTY

    510 Latitude Ln, Osprey, FL 34229
    • /2

      Est $383,000

      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

  • /60

    $10,750,000

    $1M PRICE DROP
    • 5 Beds
    • 8 Baths
    • 8,050 Sq Ft

    1216 N Casey Key Rd, Osprey, FL 34229

    This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1216 N Casey Key Rd, Osprey, FL 34229
  • /2

    $715,000

    Sold Mar 17, 2026

    319 Park Trace Blvd, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,551 Sq Ft
    • Built 2000

    Last Sold Summary

    • 5% Below List Price
    • $280/SF
    • 33 Days On Market

    Current Estimated Value $722,383

    Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

    319 Park Trace Blvd, Osprey, FL 34229
    • /2

      Est $1,029,401

      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

  • /41

    $795,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,463 Sq Ft

    127 Park Trace Blvd, Osprey, FL 34229

    Under contract-accepting backup offers. Flawless from top to bottom, this beautifully maintained Florida home offers over 3,000 sq. feet of indoor and outdoor living space, perfect for casual or elegant entertaining. With more than $175,000 in recent upgrades, this stunning water view property blends luxury with peace of mind. Highlights include a new roof, a refinished pool and spa with new

    Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

    127 Park Trace Blvd, Osprey, FL 34229
  • /2

    $645,000

    Sold Jul 31, 2025

    673 Crane Prairie Way, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,223 Sq Ft
    • Built 2003

    Last Sold Summary

    • 13% Below List Price
    • $290/SF
    • 9 Days On Market

    Current Estimated Value $653,257

    Last Listing Agent Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

    673 Crane Prairie Way, Osprey, FL 34229
    • /29

      Est $2,065,374

      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

  • /30

    $294,900

    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft

    184 Explorer Dr, Osprey, FL 34229

    Luxury Corner Residence in Osprey | Top-Rated Pine View School District.Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities.This FULLY FURNISHED 2-bedroom, 2-bathroom

    Claudia Dybala DALTON WADE INC

    184 Explorer Dr, Osprey, FL 34229
  • /2

    $362,500

    Sold Feb 23, 2026

    291 Hidden Bay Dr Unit 101, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,599 Sq Ft
    • Built 2000

    Last Sold Summary

    • 9% Below List Price
    • $227/SF
    • 58 Days On Market

    Current Estimated Value $365,235

    Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE

    291 Hidden Bay Dr Unit 101, Osprey, FL 34229
    • /2

      Est $205,691

      Not Listed For Sale

      120 Woodland Place Unit 120, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,325 Sq Ft
      • Built 1979
      120 Woodland Place Unit 120, Osprey, FL 34229

      Last Sold Summary

      • 100 Days On Market

  • /70

    $739,000

    • 3 Beds
    • 2.5 Baths
    • 2,216 Sq Ft

    347 Bayshore Dr, Osprey, FL 34229

    This custom built home is located in the Osprey subdivision Bay Acres, an established neighborhood along Little Sarasota Bay between Sarasota and Venice. It's location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Beaches, and all amenities of both cities. This home includes over 4000 sq ft of total space that includes a 2 plus car

    Sharon Sprow COLDWELL BANKER REALTY

    347 Bayshore 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 $2,286,869

    Last Listing Agent Marisa Marino BRIGHT REALTY

    896 MacEwen Dr, Osprey, FL 34229
    • /2

      Est $681,203

      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

  • /19

    $285,000

    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    51 Mac Ewen Dr Unit 14, Osprey, FL 34229

    This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area

    Steve Abbe COLDWELL BANKER REALTY

    51 Mac Ewen Dr Unit 14, 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 $3,023,233

    Last Listing Agent Kara Money KARA MONEY LLC

    112 Osprey Point Dr, Osprey, FL 34229
    • /2

      Est $559,708

      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

  • /60

    $489,000

    $90K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,555 Sq Ft

    786 Sarabay Rd Unit 19, Osprey, FL 34229

    Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is

    Michael Christo PREMIER SOTHEBYS INTL REALTY

    786 Sarabay Rd Unit 19, 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 $665,924

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

    563 Pine Ranch Rd E, Osprey, FL 34229
    • /2

      Est $877,409

      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

  • /90

    $625,000

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

    409 N Point Rd Unit 401, Osprey, FL 34229

    Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown

    Steve Abbe COLDWELL BANKER REALTY

    409 N Point Rd Unit 401, Osprey, FL 34229
  • /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 $1,464,573

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    462 E MacEwen Dr, Osprey, FL 34229
    • /2

      Est $809,827

      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

  • /85

    $625,000

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

    393 N Point Rd Unit 301, Osprey, FL 34229

    This end unit in The Meridian has been thoughtfully updated and carefully maintained. Offering 3 bedrooms and 3 full baths, it also has a dedicated study/den with pocket doors. Light and bright, this 2,594 square foot residence is spacious and offers room for comfortable and elegant living. The large master suite has a large bathroom with a walk-in shower, dual vanities and sinks and tons of

    Steve Abbe COLDWELL BANKER REALTY

    393 N Point Rd Unit 301, Osprey, FL 34229
  • /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
    • /55

      Est $912,359

      Not Listed For Sale

      792 Placid Lake Dr, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 3,360 Sq Ft
      • Built 2003
      792 Placid Lake Dr, Osprey, FL 34229

      Last Sold Summary

      • 2 Days On Market

  • /52

    $525,000

    $75K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    1140 Beachcomber Ct Unit 11, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Welcome to Blackburn Point Marina Village, where coastal elegance meets maintenance-free living near Sarasota's desired waterfront. Enjoy the boating and waterfront lifestyle you've dreamed of without the million-dollar price tag. This beautifully upgraded townhome features a bright open floor plan with luxury vinyl flooring (2025), plantation

    Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1140 Beachcomber Ct Unit 11, Osprey, FL 34229
  • /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 $645,251

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

    1303 Thornapple Dr, Osprey, FL 34229
    • /40

      Est $728,791

      Not Listed For Sale

      669 Crane Prairie Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,323 Sq Ft
      • Built 2003
      669 Crane Prairie Way, Osprey, FL 34229

      Last Sold Summary

      • 2 Days On Market

Showing Results 321 - 360, Page 9 of 18

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