Osprey, FL Homes for Sale with Pool

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  $1,089,000

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3936 Waypoint Ave, Osprey, FL 34229

  Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey, FL. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal lifestyle.Blending luxury, comfort, and

  Angelic Tassos CORCORAN DWELLINGS REALTY

  3936 Waypoint Ave, Osprey, FL 34229
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  /76

  $455,000

  • 2 Beds
  • 2 Baths
  • 1,604 Sq Ft

  508 Meadow Sweet Cir, Osprey, FL 34229

  PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in

  Bill Cantrell FLORIDA HOME TEAM LLC

  508 Meadow Sweet Cir, Osprey, FL 34229
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  $699,000

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  14041 Bellagio Way Unit 415, Osprey, FL 34229

  A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking views of the Intracoastal Waterway located in the premier gated community of The Villas at Bellagio. Upon entering the home, you are greeted by the inviting foyer leading down the art gallery-like hallway to the open family room and kitchen area. This three-bedroom, two-bathroom unit has many wonderful

  Stephen Hachey FLAT FEE MLS REALTY

  14041 Bellagio Way Unit 415, Osprey, FL 34229
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  $559,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,186 Sq Ft

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229

  Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet,

  Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229
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  $2,500,000

  • 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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  /45

  $305,000

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

  100 Navigation Cir, Osprey, FL 34229

  Welcome to Bay Street Village in Osprey, where maintenance-free Florida living awaits in this gorgeous gatedcommunity. This immaculate end-unit condo features 2 bedrooms, 2 bathrooms, and a 1-car garage. The garageis located beneath the unit and offers a private interior stairway leading to your second-floor residence.Enjoy an open-concept living and dining area perfect for

  Zita Bowers MICHAEL SAUNDERS & COMPANY

  100 Navigation Cir, Osprey, FL 34229
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  /93

  $749,900

  • 3 Beds
  • 2 Baths
  • 2,505 Sq Ft

  186 Windward Dr, Osprey, FL 34229

  Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been

  Brittany Coleman KELLER WILLIAMS ON THE WATER S

  186 Windward Dr, Osprey, FL 34229
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  /99

  $1,197,000

  • 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 comfort,

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, Osprey, FL 34229
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  $525,000

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

  811 Shadow Bay Way, Osprey, FL 34229

  Immaculate and truly move-in ready! This turnkey-furnished, spacious 2-bedroom + den, 2-bath home offers an open floor plan with gorgeous wood flooring throughout the living areas and den. The kitchen features marble countertops, an oversized island, large pantry, and quality finishes, while additional highlights include crown molding, plantation shutters, a private heated pool, electric

  Wayne Cherry PROGRAM REALTY, LLC

  811 Shadow Bay Way, Osprey, FL 34229
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  /2

  $592,249 New Construction

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

  791 S Tamiami Trail Unit 201, 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 201, Osprey, FL 34229
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  $595,000

  • 3 Beds
  • 3 Baths
  • 2,203 Sq Ft

  409 N Point Rd Unit 603, Osprey, FL 34229

  BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF! Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 full baths and a formal dining room/den. With this condo you have found a best-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private elevator to the sixth floor

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
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  $899,995

  • 3 Beds
  • 4 Baths
  • 3,561 Sq Ft

  616 Crane Prairie Way, Osprey, FL 34229

  Located in Willowbend, this expansive residence offers a rare blend of space, privacy, and long-term potential, set against tranquil water and preserve views with Oscar Scherer State Park as a stunning natural backdrop. Offering over 3,500 square feet of living space, the home provides exceptional flexibility for buyers looking to personalize a well-designed layout. High ceilings, architectural

  Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  616 Crane Prairie Way, Osprey, FL 34229
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  $574,000

  • 3 Beds
  • 2.5 Baths
  • 1,849 Sq Ft

  9590 Knightsbridge Cir, Sarasota, FL 34238

  One or more photo(s) has been virtually staged. Welcome to your beautifully updated 3 bedroom 2 1/2 bathroom, 2 car garage home in Stoneybrook at Palmer Ranch. Be ready to enjoy the large living area and open floor plan with pool and water views. Great home layout for entertaining or relaxing. This wonderful home offers a vast amount of light, is freshly painted, clean and bright and a must see!

  Kathleen Goff KATHLEEN GOFF LICENSE R.E. BROKER

  9590 Knightsbridge Cir, Sarasota, FL 34238
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  $734,900

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft

  5400 Lampiasi St, Sarasota, FL 34238

  Beautifully upgraded waterfront home with premium corner-lot privacy in the sought-after gated Esplanade at Palmer Ranch—offering direct gated access to the Legacy Trail just steps from your door. This rarely available Roma model features 2 bedrooms, 2 bathrooms plus den, an extended and oversized screened lanai, and a thoughtfully designed open floor plan ideal for both everyday living and

  Mark Quire KELLER WILLIAMS ON THE WATER S

  5400 Lampiasi St, Sarasota, FL 34238
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  /45

  $595,000

  • 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 crystal-clear pool recently resurfaced. It is loaded with curb appeal, from the pavered driveway to the pavered pool deck. As you enter the home, you are greeted with a serene view of the

  Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

  9528 Hawksmoor Ln, Sarasota, FL 34238

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