Osprey, FL Homes

• 

  

  /2

  $685,000

  Sold Jan 30, 2026

  866 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,434 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $281/SF
  • 182 Days On Market

  Current Estimated Value $675,366

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  866 Oak Briar Ln, Osprey, FL 34229
• 

  

  

  /24

  Est $790,953

  Not Listed For Sale

  130 N Creek Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1997

  130 N Creek Ln, Osprey, FL 34229

  Last Sold Summary

  • 140 Days On Market
• 

  

  

  /56

  $974,900

  $20K PRICE DROP Pending

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

  1602 Southbay Dr, Osprey, FL 34229

  Welcome to your slice of Florida paradise!Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical

  Thomas Kiessling COMPASS FLORIDA LLC

  1602 Southbay Dr, Osprey, FL 34229
• 

  

  /2

  $635,000

  Sold Jan 29, 2026

  178 Willow Bend Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $336/SF
  • 8 Days On Market

  Current Estimated Value $624,986

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  178 Willow Bend Way, Osprey, FL 34229
• 

  

  /2

  Est $508,650

  Not Listed For Sale

  544 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 2001

  544 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 7 Days On Market
• 

  

  /55

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  103 Bishops Court Rd, Osprey, FL 34229

  **LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added

  Mark Lyda GENEROUS PROPERTY

  103 Bishops Court Rd, Osprey, FL 34229
• 

  /2

  $335,000

  Sold May 14, 2026

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 2000

  Last Sold Summary

  • 16% Below List Price
  • $227/SF
  • 69 Days On Market

  Current Estimated Value $391,004

  Last Listing Agent Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229
• 

  /2

  Est $1,972,422

  Not Listed For Sale

  703 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,641 Sq Ft
  • Built 2007

  703 N MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 95 Days On Market
• 

  /2

  $617,999

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 103, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 103, Osprey, FL 34229
• 

  /2

  $1,285,000

  Sold Apr 08, 2026

  137 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,303 Sq Ft
  • Built 1996

  Last Sold Summary

  • 10% Below List Price
  • $389/SF
  • 118 Days On Market

  Current Estimated Value $1,493,571

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  137 Osprey Point Dr, Osprey, FL 34229
• 

  

  /60

  Est $504,122

  Not Listed For Sale

  455 N Shore Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft
  • Built 1966

  455 N Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 89 Days On Market
• 

  

  /55

  $497,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  120 Villa Dr Unit 120, Osprey, FL 34229

  Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  120 Villa Dr Unit 120, Osprey, FL 34229
• 

  /2

  $700,000

  Sold Oct 08, 2025

  826 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,589 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $270/SF
  • 160 Days On Market

  Current Estimated Value $709,998

  Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
• 

  /2

  Est $696,223

  Not Listed For Sale

  668 Clear Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,388 Sq Ft
  • Built 2002

  668 Clear Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 11 Days On Market
• 

  

  /42

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft

  211 Woodland Dr Unit 211, Osprey, FL 34229

  Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area

  Samantha Campbell BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  211 Woodland Dr Unit 211, Osprey, FL 34229
• 

  /2

  $585,000

  Sold Mar 27, 2026

  584 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,151 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $272/SF
  • 18 Days On Market

  Current Estimated Value $580,538

  Last Listing Agent Jack Keller JACK KELLER INC

  584 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /72

  Est $637,197

  Not Listed For Sale

  593 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 2005

  593 Crane Prairie Way, Osprey, FL 34229

  Last Sold Summary

  • 194 Days On Market
• 

  

  /74

  $799,900

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,474 Sq Ft

  1495 Landview Ln, Osprey, FL 34229

  Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool

  Pat Williams PAT WILLIAMS REALTY, LLC

  1495 Landview Ln, Osprey, FL 34229
• 

  /2

  $260,000

  Sold Jan 23, 2026

  761 Pine Run Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 7% Below List Price
  • $189/SF
  • 31 Days On Market

  Current Estimated Value $256,869

  Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

  761 Pine Run Dr, Osprey, FL 34229
• 

  /2

  Est $795,887

  Not Listed For Sale

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2006

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  Last Sold Summary

  • 42 Days On Market
• 

  

  /80

  $1,095,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,723 Sq Ft

  272 Four Knot Ln, Osprey, FL 34229

  Under contract-accepting backup offers. Welcome to this simply stunning, meticulously maintained 5-bedroom, 3-bath residence located in the highly sought-after Southbay Yacht & Racquet Club. Proudly offered by the original owner, this exceptional home showcases true pride of ownership throughout. Situated on a beautifully treed and lushly landscaped lot, the property offers privacy, elegance, and

  Andrew Peterson KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  272 Four Knot Ln, Osprey, FL 34229
• 

  /2

  $2,925,000

  Sold Sep 23, 2025

  550 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $373/SF
  • 63 Days On Market

  Current Estimated Value $2,886,326

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
• 

  

  /100

  Est $1,158,426

  Not Listed For Sale

  328 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,215 Sq Ft
  • Built 1991

  328 Pine Ranch Trail, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $489,249

  New Construction $111K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, 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 102, Osprey, FL 34229
• 

  /2

  $280,000

  Sold Feb 04, 2026

  232 Explorer Dr Unit 15, Osprey, FL 34229

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

  Last Sold Summary

  • 15% Below List Price
  • $247/SF
  • 220 Days On Market

  Current Estimated Value $279,247

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
• 

  

  /54

  Not Listed For Sale

  871 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 5,168 Sq Ft
  • Built 1990

  871 MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 226 Days On Market
• 

  /2

  $617,999

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 301, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION-STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 301, Osprey, FL 34229
• 

  /2

  $1,500,000

  Sold Jul 08, 2025

  269 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft
  • Built 1997

  Last Sold Summary

  • 16% Below List Price
  • $420/SF
  • 76 Days On Market

  Current Estimated Value $1,474,388

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
• 

  

  /65

  Est $1,823,768

  Not Listed For Sale

  482 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft
  • Built 2001

  482 E MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 212 Days On Market
• 

  

  /74

  $1,200,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  700 Faith Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. The peace and tranquility of the outdoor space is highlighted by a resort

  steve mularky LACEY REALTY INC

  700 Faith Ave, Osprey, FL 34229
• 

  /2

  $335,000

  Sold Mar 27, 2026

  172 Explorer Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $333,732

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  172 Explorer Dr, Osprey, FL 34229
• 

  /2

  Est $389,713

  Not Listed For Sale

  308 Kensey Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 1972

  308 Kensey Ln, Osprey, FL 34229

  Last Sold Summary

  • 109 Days On Market
• 

  

  /39

  $749,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229

  Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229
• 

  /2

  $995,000

  Sold Mar 05, 2026

  105 Turquoise Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,606 Sq Ft
  • Built 2001

  Last Sold Summary

  • $382/SF
  • 162 Days On Market

  Current Estimated Value $970,581

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  105 Turquoise Ln, Osprey, FL 34229
• 

  

  /30

  Est $126,907

  Not Listed For Sale

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft
  • Built 1973

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  Last Sold Summary

  • 54 Days On Market
• 

  

  /51

  $425,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  107 Sorrento Dr, Osprey, FL 34229

  This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  107 Sorrento Dr, Osprey, FL 34229
• 

  /2

  $510,000

  Sold Jan 13, 2026

  12689 Promenade Estates Blvd, Osprey, FL 34238

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $249/SF
  • 38 Days On Market

  Current Estimated Value $517,482

  Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

  12689 Promenade Estates Blvd, Osprey, FL 34238
• 

  

  /50

  Est $539,106

  Not Listed For Sale

  529 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,789 Sq Ft
  • Built 2002

  529 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 4 Days On Market
• 

  

  /46

  $999,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,086 Sq Ft

  14041 Bellagio Way Unit 318, Osprey, FL 34229

  Virtually Staged. Boaters, sunset lovers, and buyers seeking a true Gulf Coast lifestyle will appreciate this spacious waterfront condominium in The Villas at Bellagio Harbor Village, complete with a 37 foot wet slip included in the sale. This 3 bedroom plus den, 2 bath residence offers 2,086 square feet of living space, plus large lanai, private elevator entry, and beautiful west facing views

  Margot Vigar (Leonard) COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 318, Osprey, FL 34229
• 

  /2

  $3,050,000

  Sold Aug 15, 2025

  5 N Casey Key Rd, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,380 Sq Ft
  • Built 1969

  Last Sold Summary

  • 27% Below List Price
  • $1,282/SF
  • 278 Days On Market

  Current Estimated Value $3,026,017

  Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229

Showing Results 281 - 320, Page 8 of 18