Osprey, FL Homes for Sale with Pool

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  /50

  $1,685,000

  • 3 Beds
  • 3 Baths
  • 2,402 Sq Ft

  364 El Greco Dr, Osprey, FL 34229

  This exquisite waterfront residence offers a dreamlike lifestyle with expansive views of the canal and bay, making it a gem in Sorrento Shores. Boaters dream, 10,000-pound lift in your backyard, 20 minutes to Venice Inlet with access to the turquoise waters of The Gulf. On a prime cul-de-sac lot, the home boasts a stunning circular driveway adorned with majestic Royal Palms, enhancing its curb

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  364 El Greco Dr, Osprey, FL 34229
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  /92

  $1,300,000

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

  393 N Point Rd Unit 604, Osprey, FL 34229

  Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  $2,350,000

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  18 N Casey Key Rd, Osprey, FL 34229

  Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom.

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
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  $279,000

  • 2 Beds
  • 2 Baths
  • 1,729 Sq Ft

  304 Pine Run Dr, Osprey, FL 34229

  Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr., a beautifully architecturally designed property nestled in the sought-after Pine Run community in Osprey, FL. Surrounded by lush tropical landscaping and just minutes from the Gulf Coast’s pristine beaches, this residence offers the perfect blend of tranquility and

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  304 Pine Run Dr, Osprey, FL 34229
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  $1,045,000

  • 2 Beds
  • 2 Baths
  • 2,071 Sq Ft

  227 Saint James Park, Osprey, FL 34229

  **TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this

  Mark Lyda GENEROUS PROPERTY

  227 Saint James Park, Osprey, FL 34229
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  /44

  $910,000

  • 3 Beds
  • 2 Baths
  • 2,271 Sq Ft

  293 Turquoise Ln, Osprey, FL 34229

  **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

  Mark Lyda GENEROUS PROPERTY

  293 Turquoise Ln, Osprey, FL 34229
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  /64

  $699,900

  • 4 Beds
  • 3 Baths
  • 2,298 Sq Ft

  644 Rivendell Blvd, Osprey, FL 34229

  Optional Turnkey! Built in 2001, this home features high tray ceilings and a smart, functional layout.The formal living and family rooms, along with the en-suite primary bedroom, open to the lanai. The dining room includes custom built-ins, while two guest bedrooms share a hall bathroom. A private in-law suite, currently used as an office, has its own bathroom and lanai access.The

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  /51

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,559 Sq Ft

  566 Oak Bay Dr, Osprey, FL 34229

  **Seller is motivated**Welcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a classic Florida home featuring a pool with mosaic inspired ocean theme. And with no one behind you and no houses in front offers plenty of privacy. Oh, I almost forgot this home offers a wood burning fire place for those couple of cold nights a year, lol. New roof September 2022 newer water heater. This

  Greg Walters SARABAY REAL ESTATE INC

  566 Oak Bay Dr, Osprey, FL 34229
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  /68

  $324,900

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229

  Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little Sarasota Bay, this gated community offers waterfront play and relaxation. Spend your perfect day at the amenity rich community clubhouse/pool or kayaking on Intracoastal waters. This lovely two-bedroom, two-bath home is roomy and bright, offering a den/office along with a

  Kristen Redding MICHAEL SAUNDERS & COMPANY

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229
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  /62

  $409,900

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

  2251 Jessie Harbor Dr, Osprey, FL 34229

  **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

  Mark Lyda GENEROUS PROPERTY

  2251 Jessie Harbor Dr, Osprey, FL 34229
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  $2,495,000

  • 4 Beds
  • 4 Baths
  • 2,572 Sq Ft

  312 Yacht Harbor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a 6-foot depth at mean low tide, the marina can accommodate 175 boats owned by

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  312 Yacht Harbor Dr, Osprey, FL 34229
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  /61

  $550,000

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

  12689 Promenade Estates Blvd, Osprey, FL 34238

  Stunning Newer Home in Promenade Estates, Palmer Ranch. Welcome to this immaculate 4-bedroom, 2.5-bathroom single-family home situated on a prime corner lot in the sought-after Promenade Estates community, located in the heart of Palmer Ranch, Sarasota. Built in 2021, this property offers contemporary design, thoughtful upgrades, and the perfect blend of comfort and style. This bright and

  Lee Brewer RE/MAX ALLIANCE GROUP

  12689 Promenade Estates Blvd, Osprey, FL 34238
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  /55

  $845,000

  • 4 Beds
  • 4 Baths
  • 3,183 Sq Ft

  650 Crane Prairie Way, Osprey, FL 34229

  BEST PRICED HOME PER SQ FT in a 3-Mile Radius! Now Offered at $845,000 | Lease Option/Purchase Available!Live large in this 3,183 sq ft Lee Wetherington masterpiece with private pool and preserve OSCAR SCHERE PARK views in the coveted Willowbend community—just minutes from Casey Key Beach and the nationally ranked Pine View School for the Gifted. Offering over 3,180 sq ft, this home features

  Cheri Castro KELLER WILLIAMS ON THE WATER

  650 Crane Prairie Way, Osprey, FL 34229
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  /75

  $230,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  201 Woodland Dr Unit 201, Osprey, FL 34229

  Rarely available 1st floor end unit!

  Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

  201 Woodland Dr Unit 201, Osprey, FL 34229
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  /70

  $485,000

  • 2 Beds
  • 3 Baths
  • 2,837 Sq Ft

  264 Woods Point Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your

  Mark Midyett KELLER WILLIAMS ON THE WATER S

  264 Woods Point Rd, Osprey, FL 34229
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  /48

  $269,999

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

  207 Woodland Dr Unit 207, Osprey, FL 34229

  Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /91

  $399,900

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  401 N Point Rd Unit 301, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
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  /93

  $719,000

  • 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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  $1,549,000

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  401 N Point Rd Unit 901, Osprey, FL 34229

  This opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in Meridian at The Oaks Preserve, is a dream come true! A penthouse-level end unit situated on the north side of the building, it has been carefully updated and meticulously maintained. From the moment you step off your private elevator you will be impressed by this spacious unit. 10 foot ceilings,

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
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  /50

  $789,900

  • 3 Beds
  • 3 Baths
  • 3,147 Sq Ft

  3603 N Point Rd Unit 202, Osprey, FL 34229

  **ELEGANT and SPACIOUS CORNER CONDO UNIT – NEARLY 3200sf – With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned Parking spaces including 1 under building, Climate-controlled storage and much more! Crown moldings, engineered hardwood floors, expansive kitchen

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 202, Osprey, FL 34229
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  /99

  $699,000

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

  401 N Point Rd Unit 603, Osprey, FL 34229

  One or more photo(s) has been virtually staged. BEAUTIFUL FULL WATER VIEW AND 2ND FLOOR PRIVATE 2 CAR GARAGE! This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths and a formal dining room. Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 603, Osprey, FL 34229
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  /2

  $800,000

  • Land
  • 0.55 Acre
  • $1,454,545 per Acre

  0 Hidden Bay Dr, Osprey, FL 34229

  The Development Site is a lakefront parcel overlooking the community’s internal lake and clubhouse. The concept plan shows 24 2-3 bedroom units in 4 stories over parking, but the parcel has unprecedented zoning and entitlements for up to 42 units. All utilities and the roads are to the development site. The utilities, roads, and parking areas, the gated entrance and the resort-style amenities are

  Bob Morris SVN COMMERCIAL ADVISORY GROUP

  0 Hidden Bay Dr, Osprey, FL 34229
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  /4

  $527,904 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, Osprey, FL 34229

  Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $527,904. 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
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  $3,705,000

  • 4 Beds
  • 5.5 Baths
  • 8,635 Sq Ft

  112 Osprey Point Dr, Osprey, FL 34229

  Premier Waterfront Opportunity in The Oaks BaysideThis grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to

  Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
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  /68

  $639,000

  • 2 Beds
  • 2 Baths
  • 1,766 Sq Ft

  9492 Forest Hills Cir, Sarasota, FL 34238

  Welcome to this beautifully appointed 2-bedroom, 2-bath, Plus a Den villa with stunning panoramic views of the golf course and a tranquil pond—an ideal setting for elegant, maintenance-free living. Located in the highly desirable Forest Hills section of Stoneybrook at Palmer Ranch, this villa features a spacious split floor plan that offers privacy for guests, with a guest bedroom and full bath.

  Mimi Kruk MICHAEL SAUNDERS & COMPANY

  9492 Forest Hills Cir, Sarasota, FL 34238
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  /46

  $725,000

  • 3 Beds
  • 2 Baths
  • 1,918 Sq Ft

  5301 Bartolomeo St, Sarasota, FL 34238

  Discover the exceptional lifestyle offered in Esplanade on Palmer Ranch with this beautiful Arrezo model home, perfectly situated on a private cul-de-sac. This vibrant and active community boasts a wealth of amenities, including the Bahama Bar for dining and social activities, pickleball and tennis courts, a well-equipped fitness center, and a breathtaking resort-style pool that could rival the

  Anne Friedland BLUESRQ REAL ESTATE INC

  5301 Bartolomeo St, Sarasota, FL 34238
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  $1,600,000

  • 3 Beds
  • 3 Baths
  • 2,994 Sq Ft

  5329 Trails Bend Ct, Sarasota, FL 34238

  Discover your dream home in the prestigious Legacy Estates, where luxury meets comfort in a resort-style setting. This exquisite property features a private courtyard and boasts high ceilings with an open floorplan, perfect for modern living and entertaining. With three ensuite bedrooms and ample linen closets, this home offers both privacy and convenience. The interior showcases numerous

  Coreen Wilde MICHAEL SAUNDERS & COMPANY

  5329 Trails Bend Ct, Sarasota, FL 34238
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  /70

  $584,000

  • 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. 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 is freshly painted, clean and bright and a must see! The kitchen features new wood cabinets,

  Kathleen Goff KATHLEEN GOFF LICENSE R.E. BROKER

  9590 Knightsbridge Cir, Sarasota, FL 34238

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