Homes for Sale in 34229

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  /41

  $700,000

  $19K PRICE DROP

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

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229

  Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront CommunityThis 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan

  Cathy Rustin FIRST LIGHT REAL ESTATE

  242 Hidden Bay Dr Unit 602, Osprey, FL 34229
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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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  /97

  $1,900,000

  • 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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  /52

  $1,165,000

  $34K PRICE DROP

  • 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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  /89

  $1,495,000

  • 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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  /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
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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
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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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  /99

  $1,095,000

  $102K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft

  403 Longbow Trail, Osprey, FL 34229

  Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail.This charming home offers a perfect blend of

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, Osprey, FL 34229
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  /79

  $739,000

  • 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
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  /75

  $1,950,000

  $350K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 4,346 Sq Ft

  538 Dove Pointe, Osprey, FL 34229

  **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

  Mark Lyda GENEROUS PROPERTY

  538 Dove Pointe, Osprey, FL 34229
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  /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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  /41

  $419,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  524 Sarabay Rd, Osprey, FL 34229

  Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

  Ibetta Giannone SUN N SAND REAL ESTATE LLC

  524 Sarabay Rd, Osprey, FL 34229
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  /49

  $1,495,000

  • 3 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  360 N Point Rd, Osprey, FL 34229

  Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger.

  Steve Abbe COLDWELL BANKER REALTY

  360 N Point Rd, Osprey, FL 34229
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  /25

  $600,000

  • Land
  • 14,810 Sq Ft
  • $1,764,706 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community in Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. Featuring a generous 100-foot frontage and dimensions that allow for multiple building possibilities, this property is ideal for those looking to build

  Matthew Charland LLC PREMIER SOTHEBYS INTL REALTY

  458 N Shore Dr, Osprey, FL 34229
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  /45

  $540,000

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,007 Sq Ft

  9528 Hawksmoor Ln, Sarasota, FL 34238

  Welcome to 9528 Hawksmoor Lane, located in the highly sought-after gated community of Stoneybrook Estates on Palmer Ranch. This spacious home features over 2,000 sq. ft. of living space, a two-car garage, and a pool recently resurfaced. It is loaded with curb appeal, from the pavered driveway to the pavered pool deck. Upon entering the home, you will find high ceilings, a comfortable living room

  Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

  9528 Hawksmoor Ln, Sarasota, FL 34238
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  /50

  $4,795,000

  • 5 Beds
  • 3.5 Baths
  • 4,914 Sq Ft

  4678 Silent Creek Way, Nokomis, FL 34275

  Tucked away at the end of a quiet road on a breathtakingly private one-acre homesite, this extraordinary luxury gated estate overlooks the serene waters of South Creek with the untouched natural beauty of Oscar Scherer State Park creating an incomparable backdrop. Completely reimagined with a sophisticated contemporary aesthetic, this custom-built residence blends timeless architecture with

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4678 Silent Creek Way, Nokomis, FL 34275

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