Osprey, FL Homes for Sale with Garage

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  /60

  $11,750,000

  • 5 Beds
  • 8 Baths
  • 8,050 Sq Ft

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /92

  $1,775,000 Pre-Foreclosure

  • 4 Beds
  • 4 Baths
  • 4,001 Sq Ft

  75 Osprey Point Dr, Osprey, FL 34229

  **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

  Mark Lyda GENEROUS PROPERTY

  75 Osprey Point Dr, Osprey, FL 34229
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  /78

  $800,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  102 Windward Dr, Osprey, FL 34229

  Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both

  David Cyr WILLIAM RAVEIS REAL ESTATE

  102 Windward Dr, Osprey, FL 34229
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  /78

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 4,781 Sq Ft

  1042 N Casey Key Rd, Osprey, FL 34229

  If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay breezes and water views, while majestic oaks and lush

  Brandy Sheldon COLDWELL BANKER REALTY

  1042 N Casey Key Rd, Osprey, FL 34229
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  /62

  $395,000

  • 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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  /59

  $600,000

  • 4 Beds
  • 2 Baths
  • 2,133 Sq Ft

  711 Shadow Bay Way, Osprey, FL 34229

  Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the

  Susan Keal MICHAEL SAUNDERS & COMPANY

  711 Shadow Bay Way, Osprey, FL 34229
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  /46

  $545,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include:

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
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  /100

  $1,690,000

  • 3 Beds
  • 4.5 Baths
  • 4,364 Sq Ft

  76 Osprey Point Dr, Osprey, FL 34229

  COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available

  Steve Abbe COLDWELL BANKER REALTY

  76 Osprey Point Dr, Osprey, FL 34229
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  /87

  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,473 Sq Ft

  140 N Casey Key Rd, Osprey, FL 34229

  LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibrant 3-bed, 3.5-bath waterfront retreat, perfectly positioned along the Intracoastal Waterway with dazzling, front-row views. Designed for unforgettable days on the water, this home features a stunning Aqua-Tech infinity edge heated pool with therapy jet ledge, where you can unwind while watching boats, jet

  Rhonda Carder EXP REALTY LLC

  140 N Casey Key Rd, Osprey, FL 34229
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  /96

  $1,500,000

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

  385 N Point Rd Unit 704, Osprey, FL 34229

  Experience breathtaking views of the Bay and Gulf from this spacious 3 bedroom, 3 bath end unit, featuring a separate dining room and den. Completely updated and meticulously maintained, this unit is beautifully appointed and custom features abound. A private elevator takes you to a majestic foyer which opens to the great room. Facing west the views are gorgeous from sunrise to sunset. The

  Steve Abbe COLDWELL BANKER REALTY

  385 N Point Rd Unit 704, Osprey, FL 34229
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  /77

  $7,100,000

  • 4 Beds
  • 5.5 Baths
  • 4,096 Sq Ft

  121 N Casey Key Rd, Osprey, FL 34229

  Newly Remodeled Gulf-Front Mediterranean Villa on Casey KeyFramed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
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  /87

  $685,000

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  571 Pine Ranch Rd E, Osprey, FL 34229

  One of the largest homes in Bay Oaks Estates, this 5-bed, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush landscaping, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural light

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

  571 Pine Ranch Rd E, Osprey, FL 34229
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  /37

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft

  455 N Shore Dr, Osprey, FL 34229

  Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment. Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42 boat

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  455 N Shore Dr, Osprey, FL 34229
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  /92

  $875,000

  • 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 of

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  /42

  $879,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,935 Sq Ft

  327 Park Trace Blvd, Osprey, FL 34229

  LOOK NO FURTHER! This immaculate, lake-view four-bedroom/ three-bath home is MOVE-IN READY. Completewith a NEW 60K Tile ROOF, PGT Impact Windows throughout and new A/C (2024)! Freshly painted interior fromtop to bottom with Regal select Benjamin Moore paint, sparkling epoxy garage floor, New GE 5 burner range withCrisp mode, walk in pantry, beautifully Updated landscaping, new modern

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  327 Park Trace Blvd, Osprey, FL 34229
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  /44

  $679,900

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

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

  This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid

  Cindy Migone PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
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  /88

  $2,700,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /66

  $895,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  238 Lookout Point Dr, Osprey, FL 34229

  This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious

  Susanne Losso COLDWELL BANKER REALTY

  238 Lookout Point Dr, Osprey, FL 34229
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  /13

  $199,000

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  106 Villa Dr Unit 106, Osprey, FL 34229

  Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and

  Dan Ivanov KONA REALTY

  106 Villa Dr Unit 106, Osprey, FL 34229
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  /48

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  597 Oak River Ct, Osprey, FL 34229

  Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator,

  Mairead Smialek COLDWELL BANKER REALTY

  597 Oak River Ct, Osprey, FL 34229
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  /48

  $635,000

  • 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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  /76

  $1,089,000 Open House 1/18

  • 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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  /32

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 2,572 Sq Ft

  135 Tina Island Dr, Osprey, FL 34229

  Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and

  Cliff Glansen FLATFEE.COM

  135 Tina Island Dr, Osprey, FL 34229
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  /71

  $585,000 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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  /96

  $2,595,000

  • 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 Open Sun 1PM - 4PM

  • 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 Open Sun 1:30PM - 4PM

  • 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, 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 professionally

  Brittany Coleman KELLER WILLIAMS ON THE WATER S

  186 Windward Dr, Osprey, FL 34229
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  /99

  $1,197,000 Open Sun 2PM - 4PM

  • 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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  /51

  $463,000

  • 2 Beds
  • 2 Baths
  • 2,148 Sq Ft

  32 Bay Ave, Osprey, FL 34229

  Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless

  Jennifer Pereira LOKATION

  32 Bay Ave, Osprey, FL 34229
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  /82

  $475,000

  • 2 Beds
  • 2 Baths
  • 1,425 Sq Ft

  1102 Jessie Harbor Dr, Osprey, FL 34229

  Welcome home! This GULF ACCESS, WATERFRONT condo is ready for its new owners. Fully updated, this 2 BED, 2 BATH residence with a 1 CAR GARAGE is ideally positioned at the END OF A CANAL, offering privacy, open water views, and MILLION-DOLLAR SUNSET VIEWS every night. Located within a GATED community spanning approximately 11 acres, this home delivers both serenity and an active Florida

  Mackenzie Davis-Mahan DOWNING FRYE REALTY, INC.

  1102 Jessie Harbor Dr, Osprey, FL 34229
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  /85

  $679,000

  • 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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  /56

  $960,000

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

  616 Crane Prairie Way, Osprey, FL 34229

  This spacious residence offers over 3,500 square feet of thoughtfully designed living space that blends comfort, flexibility, and refined Florida style. From the moment you step inside, elevated and vaulted ceilings, architectural details, and abundant natural light create an inviting sense of openness. A flowing floor plan seamlessly connects the main living areas, anchored by a well-appointed

  Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  616 Crane Prairie Way, Osprey, FL 34229
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  /69

  $589,000

  • 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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  /86

  $749,900

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

  5400 Lampiasi St, Sarasota, FL 34238

  Experience resort-style living in the gated Esplanade on Palmer Ranch. This rarely available Roma model offers 2 bedrooms, 2 baths plus den, and oversized screened lanai. Ideally located on a premium corner waterfront lot with privacy, beautiful views, and direct gated Legacy Trail access just steps away. Structural upgrades include an extended kitchen, gas line on lanai, trey ceilings, primary

  Mark Quire KELLER WILLIAMS ON THE WATER S

  5400 Lampiasi St, Sarasota, FL 34238
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  /45

  $615,000

  • 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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