Osprey, FL Homes for Sale with Pool

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  /86

  $655,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  57 Bishops Court Rd Unit 121, Osprey, FL 34229

  Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architecturally designed, this classic Georgian style townhouse features two bedrooms, two full ensuite baths, one half bath, a spacious great room, and a large terrace overlooking a lake. A welcoming foyer leads to the expansive great room where high ceilings,

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  57 Bishops Court Rd Unit 121, Osprey, FL 34229
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  /77

  $1,175,000

  $114K 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
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  /2

  $540,749

  New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 302, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. 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 302, Osprey, FL 34229
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  /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
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  /31

  $695,000

  • Land
  • 25,700 Sq Ft
  • $1,177,966 per Acre

  216 Osprey Point Dr, Osprey, FL 34229

  One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural

  Judie Berger PREMIER SOTHEBY'S INTERNATIONAL REALTY

  216 Osprey Point Dr, Osprey, FL 34229
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  /51

  $749,000

  $22K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  759 Fordingbridge Way, Osprey, FL 34229

  Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a

  Steven Koleno BEYCOME OF FLORIDA LLC

  759 Fordingbridge Way, Osprey, FL 34229
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  /60

  $579,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  1367 Thornapple Dr, Osprey, FL 34229

  Discover unparalleled luxury in this exquisite Lee Wetherington-built residence, ideally in Willowbend within Osprey. A grand entry hall with high-end finishes, tray ceilings and rich crown molding welcomes you to a home meticulously perfected by discerning sellers. This ideally positioned home boasts a 1⁄4+ acre homesite with an expansive front yard, a roomy side-entry paver newly sealed

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1367 Thornapple Dr, Osprey, FL 34229
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  /83

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 3,771 Sq Ft

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County.Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort,

  Angelic Tassos CORCORAN DWELLINGS REALTY

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
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  /91

  $475,000

  $200K PRICE DROP

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

  401 N Point Rd Unit 301, Osprey, FL 34229

  Virtually Staged. Short Sale. 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 touches on it and

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
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  /95

  $625,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3621 N Point Rd Unit 301, Osprey, FL 34229

  Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut

  Steve Abbe COLDWELL BANKER REALTY

  3621 N Point Rd Unit 301, Osprey, FL 34229
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  /48

  $599,000

  $86K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
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  /38

  $899,995

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft

  14021 Bellagio Way Unit 309, Osprey, FL 34229

  Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy

  Tristin Hopler COMPASS FLORIDA, LLC

  14021 Bellagio Way Unit 309, Osprey, FL 34229
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  /54

  $880,000

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

  401 N Point Rd Unit 504, Osprey, FL 34229

  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 private 2-car garage just steps to the

  Lenore Treiman MICHAEL SAUNDERS & COMPANY

  401 N Point Rd Unit 504, Osprey, FL 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 Community This 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 features

  Cathy Rustin FIRST LIGHT REAL ESTATE

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

  $643,749

  New Construction

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

  791 S Tamiami Trail Unit 303, 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 303, Osprey, FL 34229
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  /2

  $514,999

  New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 202, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. 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 202, Osprey, FL 34229
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  /69

  $679,000

  $19K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  33 Bishops Court Rd Unit 118, Osprey, FL 34229

  **EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living

  Mark Lyda GENEROUS PROPERTY

  33 Bishops Court Rd Unit 118, 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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  /70

  $694,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  260 Hidden Bay Dr Unit B-304, Osprey, FL 34229

  The Boca Residence: Spacious Living & Resort StyleDiscover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal

  Janice Martin ENGEL & VOELKERS VENICE DOWNTOWN

  260 Hidden Bay Dr Unit B-304, 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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  /43

  $395,000

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

  7204 Jessie Harbor Dr, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally

  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

  Open Sat 11AM - 12:30PM $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 comfort,

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, 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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  /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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  /79

  $328,000

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  173 Navigation Cir Unit 107, Osprey, FL 34229

  Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances.

  Tim Weller EXIT KING REALTY

  173 Navigation Cir Unit 107, Osprey, FL 34229
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  /64

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  764 Sarabay Rd Unit 8, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  764 Sarabay Rd Unit 8, Osprey, FL 34229
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  /77

  $318,000

  $22K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  4304 Expedition Way Unit 105, Osprey, FL 34229

  Virtually Staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel

  Tim Weller EXIT KING REALTY

  4304 Expedition Way Unit 105, Osprey, FL 34229
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  /71

  $569,000

  Open Sun 12PM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 1,741 Sq Ft

  9532 Forest Hills Cir, Sarasota, FL 34238

  *One or more photos have been virtually staged* Experience luxurious living at its finest in this stunning, renovated villa located in the coveted Stoneybrook Golf & Country Club. Boasting stunning views of both the picturesque pond and the newly redesigned golf course, your dream home awaits! This spacious 2-bedroom, 2-bathroom villa offers over 1,700 sq ft of beautifully designed, open-concept

  Elisa Santamaria CORCORAN DWELLINGS REALTY

  9532 Forest Hills Cir, Sarasota, FL 34238
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  /100

  $2,299,000

  $201K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 5,171 Sq Ft

  5301 Greenbrook Dr, Sarasota, FL 34238

  Opportunities like this are rare within the exclusive Legacy Estates at Esplanade on Palmer Ranch. This exceptional two-story Gulf Coast residence offers 5 bedrooms, 4 full baths, 2 half baths, and 5,171 square feet designed for luxury living, multigenerational flexibility, executive work-from-home, and elevated entertaining. Perfectly positioned on a private corner homesite with preserve views

  Mark Quire KELLER WILLIAMS ON THE WATER S

  5301 Greenbrook Dr, Sarasota, FL 34238
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  /70

  $759,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,926 Sq Ft

  5328 Popoli Way, Sarasota, FL 34238

  This stunning newly painted exterior Arezzo model is beautifully landscaped and located in Esplanade on Palmer Ranch - Sarasota’s premier gated resort-style community. This property, located on a quiet cull-de-sac street, is being offered TURNKEY, FULLY FURNISHED featuring over $75,000 in premium upgrades. The home features a light and airy open concept design with 3 bedrooms, 2 bathrooms plus a

  Pat Williams PAT WILLIAMS REALTY, LLC

  5328 Popoli Way, 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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