Osprey, FL Homes

• 

  

  /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 $2,943,791

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
• 

  

  

  /60

  Est $498,583

  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

  Last Listing Agent Bo Fuller FULLER GROUP
• 

  

  

  /50

  $1,775,000

  Open Sun 1PM - 4PM $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,411 Sq Ft

  206 Four Knot Ln, Osprey, FL 34229

  Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club/Marina

  Leighton Allenby Realty One Group MVP

  206 Four Knot Ln, 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 $276,525

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
• 

  

  /2

  Est $691,920

  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

  Last Listing Agent Cheryl Guentner RE/MAX PALM
• 

  

  /4

  $39,500

  $3K PRICE DROP

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas 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 Point Bridge), this slip fits boats up to 33L x 9.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit CASEY 11, 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 $330,203

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  172 Explorer Dr, Osprey, FL 34229
• 

  

  /72

  Est $595,118

  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

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.
• 

  

  /46

  $499,900

  $45K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Beautifully renovated and move-in ready, this exceptional property offers the perfect blend of privacy, comfort, and investment potential. Situated on over half an acre along a private, tree-lined street, the home is surrounded by lush tropical landscaping, creating a peaceful oasis just minutes from everything Sarasota has to offer.Step inside to

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
• 

  /2

  $310,000

  Sold Aug 26, 2026

  2251 Jessie Harbor Dr Unit 2101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2006

  Last Sold Summary

  • 14% Below List Price
  • $221/SF
  • 17 Days On Market

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

  2251 Jessie Harbor Dr Unit 2101, Osprey, FL 34229
• 

  /2

  Est $770,674

  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

  Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE
• 

  

  /74

  $1,400,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 3,246 Sq Ft

  1474 Landview Ln, Osprey, FL 34229

  Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are at a top resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water

  Pat Williams PAT WILLIAMS REALTY, LLC

  1474 Landview Ln, 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 $981,369

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  105 Turquoise Ln, Osprey, FL 34229
• 

  

  /100

  Est $1,124,408

  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

  Last Listing Agent Sally Green HOMESMART
• 

  

  /61

  $320,000

  Open Sat 12PM - 3PM $25K PRICE DROP Under Contract

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

  89 Navigation Cir, Osprey, FL 34229

  Under contract-accepting backup offers. Virtually Staged. DISCOVER A LIMITED-TIME OPPORTUNITY! ?A SPECIAL OPPORTUNITY IS AVAILABLE FOR BUYERS WITH AN ACCEPTED PURCHASE CONTRACT ON OR BEFORE AUGUST 30, 2026. CONTACT THE LISTING AGENT FOR DETAILS.Experience the perfect blend of comfort, convenience, and Florida lifestyle in this beautifully maintained first-floor residence located in the

  Jozefina Polimirova KW COASTAL LIVING II

  89 Navigation Cir, 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 $520,870

  Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

  12689 Promenade Estates Blvd, Osprey, FL 34238
• 

  /2

  Est $986,767

  Not Listed For Sale

  678 Clear Creek Dr, Osprey, FL 34229

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

  678 Clear Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Dena Dominiczak EXIT KING REALTY
• 

  

  /96

  $2,850,000

  $400K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,665 Sq Ft

  14401 Masthead Dr, Osprey, FL 34229

  Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you

  Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  14401 Masthead Dr, Osprey, FL 34229
• 

  /2

  $285,900

  Sold Aug 17, 2026

  120 Woodland Place Unit 120, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $216/SF
  • 5 Days On Market

  Current Estimated Value $210,871

  Last Listing Agent Kim Kruysman EXP REALTY LLC

  120 Woodland Place Unit 120, Osprey, FL 34229
• 

  

  /65

  Est $1,896,784

  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

  Last Listing Agent David Butler Jr RE/MAX ALLIANCE GROUP
• 

  

  /3

  $269,000

  480 Blackburn Point Rd Unit 6, Osprey, FL 34229

  A rare find in Sarasota, 1 of 6 total with only 2 that haven't recently sold, this covered 50 ft x 15 x 15 wet slip at Osprey Harbor Village offers the perfect blend of protection, convenience, and value. Eligible for boat lift! Located at 480 Blackburn Point Road in Osprey, just off the Intracoastal Waterway, this sheltered slip keeps your yacht out of the Florida sun with quick access north to

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  480 Blackburn Point Rd Unit 6, Osprey, FL 34229
• 

  /2

  $1,700,000

  Sold Jul 17, 2026

  401 Walls Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,387 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $388/SF
  • 138 Days On Market

  Current Estimated Value $1,751,348

  Last Listing Agent Andrea Stultz ENGEL + VOELKERS SARASOTA

  401 Walls Way, Osprey, FL 34229
• 

  /2

  Est $395,028

  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

  Last Listing Agent Tracey Punzone UKEEPCOMMISSION REAL ESTATE
• 

  

  /42

  $609,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  619 Oak River Ct, Osprey, FL 34229

  Under contract-accepting backup offers. Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor

  Ross Fishman FISHMAN GROUP REALTY LLC

  619 Oak River Ct, Osprey, FL 34229
• 

  /2

  $540,000

  Sold Aug 07, 2026

  523 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,399 Sq Ft
  • Built 1998

  Last Sold Summary

  • $225/SF
  • 20 Days On Market

  Current Estimated Value $538,623

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  523 Oak Bay Dr, Osprey, FL 34229
• 

  

  /30

  Est $123,329

  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

  Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE
• 

  

  /66

  $6,475,000

  $625K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,096 Sq Ft

  121 N Casey Key Rd, Osprey, FL 34229

  Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting.Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, 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 $750,511

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
• 

  

  /50

  Est $522,101

  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

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
• 

  

  /62

  $1,100,000

  $100K PRICE DROP

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

  385 N Point Rd Unit 304, Osprey, FL 34229

  **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 304, 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 $794,572

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  529 Habitat Blvd, Osprey, FL 34229
• 

  

  /68

  Est $865,823

  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

  Last Listing Agent Brie Bender INNOVATE REAL ESTATE
• 

  /2

  $2,750,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,323 Sq Ft

  447 E MacEwen Dr, Osprey, FL 34229

  Experience refined living in this extraordinary, elegant home. With 3 bedrooms and 4.5 baths it offers expansive lake and golf course views from its premier position along the Heron Course. Designed for both grand entertaining and everyday comfort, the home features generous living spaces, a bright open kitchen overlooking the family room with wood burning fireplace, and a luxurious primary suite

  Steve Abbe COLDWELL BANKER REALTY

  447 E MacEwen Dr, 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 $561,908

  Last Listing Agent Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
• 

  /2

  Est $711,906

  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

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

  

  /70

  $1,100,000

  $189K 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
• 

  /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 $719,118

  Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

  319 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  Est $2,547,497

  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

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /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
• 

  /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 $357,712

  Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229

Showing Results 281 - 320, Page 8 of 18