Homes in ZIP Code 34229

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  /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
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  /39

  Est $700,253

  Not Listed For Sale

  1096 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft
  • Built 2000

  1096 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /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
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  /2

  $3,500,000

  Sold Dec 17, 2025

  431 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,006 Sq Ft
  • Built 1979

  Last Sold Summary

  • 19% Below List Price
  • $1,164/SF
  • 11 Days On Market

  Current Estimated Value $3,528,970

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  Est $749,022

  Not Listed For Sale

  1000 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,441 Sq Ft
  • Built 2003

  1000 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Jody Callan PREMIER SOTHEBYS INTL REALTY
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  /41

  $700,000

  Open Sun 1PM - 4PM $19K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229

  Penthouse level residence with ALL NEW APPLIANCES, including washer and dryer, complemented by beautiful water views.From its sixth-floor penthouse setting, this waterfront residence at Hidden Bay opens to expansive views across Little Sarasota Bay and the Intracoastal Waterway, with the Gulf beyond Casey Key in the distance. High ceilings, tall interior doors, and abundant natural light

  Cathy Rustin FIRST LIGHT REAL ESTATE

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229
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  /2

  $535,000

  Sold Jun 03, 2026

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $277/SF
  • 100 Days On Market

  Current Estimated Value $541,133

  Last Listing Agent Susan Retzke RE/MAX PALM

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
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  /2

  Est $636,157

  Not Listed For Sale

  519 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft
  • Built 2003

  519 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /71

  $275,000

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft

  51 MacEwen Dr Unit 12, Osprey, FL 34229

  Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is

  Steve Abbe COLDWELL BANKER REALTY

  51 MacEwen Dr Unit 12, Osprey, FL 34229
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  /2

  $1,105,000

  Sold Jul 17, 2026

  272 Four Knot Ln, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 2,723 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $406/SF
  • 2 Days On Market

  Current Estimated Value $1,099,704

  Last Listing Agent Andrew Peterson EVOLVE REAL ESTATE

  272 Four Knot Ln, Osprey, FL 34229
• 

  

  /55

  Est $574,469

  Not Listed For Sale

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Built 2004

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Last Sold Summary

  • 363 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  /97

  $1,900,000

  Pending

  • 5 Beds
  • 7.5 Baths
  • 5,986 Sq Ft

  916 MacEwen Dr, Osprey, FL 34229

  Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness.

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  916 MacEwen Dr, Osprey, FL 34229
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  /2

  $530,000

  Sold Jun 11, 2026

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 31 Days On Market

  Current Estimated Value $523,754

  Last Listing Agent Christine Green COLDWELL BANKER REALTY

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229
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  /2

  Est $532,444

  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

  Last Listing Agent Kathy White PREFERRED SHORE LLC
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  /100

  $1,700,000

  • 3 Beds
  • 3 Baths
  • 3,118 Sq Ft

  141 Sugar Mill Dr, Osprey, FL 34229

  Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thoughtful design throughout. Behind the gates of The Oaks Bayside, it is beautifully situated, set back on a lot that offers peace and privacy. The open kitchen is a home chef’s dream and serves as the centerpiece of the home.

  Steve Abbe COLDWELL BANKER REALTY

  141 Sugar Mill Dr, Osprey, FL 34229
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  /2

  $1,265,000

  Sold Jun 01, 2026

  1471 Shoal Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,798 Sq Ft
  • Built 1985

  Last Sold Summary

  • 16% Below List Price
  • $452/SF
  • 47 Days On Market

  Current Estimated Value $1,270,728

  Last Listing Agent Lauren Doyle DALTON WADE INC

  1471 Shoal Way, Osprey, FL 34229
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  /2

  Est $417,400

  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

  Last Listing Agent Tracey Fiedler DALTON WADE INC
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  /52

  $1,165,000

  $34K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  1527 Buoy Ln, Osprey, FL 34229

  Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage

  Matthew Lewis BRIGHT REALTY

  1527 Buoy Ln, Osprey, FL 34229
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  /2

  $1,325,000

  Sold Aug 25, 2026

  486 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,939 Sq Ft
  • Built 1981

  Last Sold Summary

  • 5% Below List Price
  • $451/SF
  • 3 Days On Market

  Current Estimated Value $1,377,008

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  486 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  Est $743,747

  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

  Last Listing Agent Christiana Kopetzky MICHAEL SAUNDERS & COMPANY
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  /89

  $1,495,000

  Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft

  226 Saint James Park, Osprey, FL 34229

  Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities

  Justin Brunswick KELLER WILLIAMS ON THE WATER S

  226 Saint James Park, Osprey, FL 34229
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  /2

  $164,000

  Sold May 14, 2026

  200 Woodland Dr Unit 200, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 45 Days On Market

  Current Estimated Value $167,552

  Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  200 Woodland Dr Unit 200, Osprey, FL 34229
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  /2

  Est $266,371

  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

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC
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  /43

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft

  7204 Jessie Harbor Dr, Osprey, FL 34229

  **BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates.

  Mark Lyda GENEROUS PROPERTY

  7204 Jessie Harbor Dr, Osprey, FL 34229
• 

  /2

  $2,400,000

  Sold Jan 09, 2026

  432 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,640 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $659/SF
  • 7 Days On Market

  Current Estimated Value $2,386,216

  Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
• 

  

  /22

  Est $554,020

  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

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
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  /96

  $2,399,000

  $196K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  49 Osprey Point Dr, Osprey, FL 34229

  Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

  Jonathan Abrams MICHAEL SAUNDERS & COMPANY

  49 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  $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 $281,676

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

  4173 Frontier Ln, Osprey, FL 34229
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  /2

  Est $1,702,134

  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

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  /49

  $299,990

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

  4296 Expedition Way Unit 104, Osprey, FL 34229

  Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining

  Pamela Kurpiewski EXP REALTY LLC

  4296 Expedition Way Unit 104, 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 $474,143

  Last Listing Agent Pamela Strom RE/MAX PALM

  1363 New Forest Ln, Osprey, FL 34229
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  /78

  Est $734,272

  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

  Last Listing Agent David Cyr WILLIAM RAVEIS - FLORIDA LLC
• 

  /2

  $2,800,000

  Pending

  • 4 Beds
  • 4 Baths
  • 4,188 Sq Ft

  662 Fernwalk Ln, Osprey, FL 34229

  Ideally positioned on a quiet interior cul-de-sac this beautifully updated 4 bedroom, 4 bath home is located behind the gates of The Oaks Bayside. The residence features 16 ft and vaulted ceilings, white oak and marble flooring, custom crown molding, plantation shutters and extensive built-ins. The chef’s kitchen boasts marble countertops, custom hardwood cabinetry, a galley workstation sink, and

  Steve Abbe COLDWELL BANKER REALTY

  662 Fernwalk Ln, 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
• 

  /2

  Est $695,029

  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

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

  

  /79

  $719,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,328 Sq Ft

  299 Turquoise Ln, Osprey, FL 34229

  Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in

  Mick Jordan BRIGHT REALTY

  299 Turquoise Ln, Osprey, FL 34229
• 

  /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 $213,662

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

  362 Pine Run Dr Unit 362, Osprey, FL 34229
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  /41

  Est $670,506

  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

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

  

  /100

  $5,999,999

  • 4 Beds
  • 4.5 Baths
  • 5,337 Sq Ft

  313 Lookout Point Dr, Osprey, FL 34229

  Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up

  Natalie Gutwein MICHAEL SAUNDERS & COMPANY

  313 Lookout 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 $574,918

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  767 Fordingbridge Way, Osprey, FL 34229

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