Osprey, FL Homes for Sale with Garage

• 

  

  

  /75

  $760,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,474 Sq Ft

  1495 Landview Ln, Osprey, FL 34229

  Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool

  Pat Williams PAT WILLIAMS REALTY, LLC

  1495 Landview Ln, Osprey, FL 34229
• 

  

  

  /43

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft

  2046 Cordes St, Osprey, FL 34229

  Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The

  Susan Mondello MICHAEL SAUNDERS & COMPANY

  2046 Cordes St, Osprey, FL 34229
• 

  

  

  /39

  $719,000

  New Construction $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229

  Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229
• 

  

  

  /38

  $165,900

  $6K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  701 Pine Run Dr, Osprey, FL 34229

  Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a

  Pat Williams PAT WILLIAMS REALTY, LLC

  701 Pine Run Dr, Osprey, FL 34229
• 

  

  

  /30

  $284,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  184 Explorer Dr, Osprey, FL 34229

  Luxury Corner Residence in Osprey | Top-Rated Pine View School District.Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities.This FULLY FURNISHED 2-bedroom, 2-bathroom

  Claudia Dybala DALTON WADE INC

  184 Explorer Dr, Osprey, FL 34229
• 

  

  /62

  $599,000

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

  5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229

  Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence

  Stuart Lawrence MICHAEL SAUNDERS & COMPANY

  5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229
• 

  

  /50

  $2,199,999

  • 4 Beds
  • 3.5 Baths
  • 4,578 Sq Ft

  154 Lookout Point Dr, Osprey, FL 34229

  Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle.The heart of the home is a completely renovated kitchen featuring quartz

  Stephen Hachey FLAT FEE MLS REALTY

  154 Lookout Point Dr, Osprey, FL 34229
• 

  

  /54

  $850,000

  • 4 Beds
  • 3 Baths
  • 2,468 Sq Ft

  144 Park Trace Blvd, Osprey, FL 34229

  Beautiful 4-bedroom, 3-bath pool home with 3-car garage. This home offers the space, upgrades and features you've been looking for. Park Trace Estates is a well-established residential community in Osprey Florida. Perfectly positioned between Sarasota and Venice providing easy access to nearby beaches, restaurants, Tiki bars, biking trails, parks, great schools and so much more! This four-bedroom

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  144 Park Trace Blvd, Osprey, FL 34229
• 

  

  /66

  $6,475,000

  $625K PRICE DROP

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

  121 N Casey Key Rd, Osprey, FL 34229

  Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting.Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
• 

  

  /62

  $1,100,000

  $100K PRICE DROP

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

  385 N Point Rd Unit 304, Osprey, FL 34229

  **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 304, Osprey, FL 34229
• 

  

  /70

  $1,100,000

  $189K 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
• 

  

  /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
• 

  

  /47

  $3,295,000

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

  135 Tina Island Dr, Osprey, FL 34229

  **EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid

  Mark Lyda GENEROUS PROPERTY

  135 Tina Island Dr, Osprey, FL 34229
• 

  

  /51

  $700,000

  $27K PRICE DROP

  • 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
• 

  

  /83

  $798,000

  $52K PRICE DROP

  • 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. PRICE IMPROVED OVER $50K!!!! 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

  Angelic Tassos CORCORAN DWELLINGS REALTY

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
• 

  

  /95

  $525,000

  $100K PRICE DROP

  • 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
• 

  

  /58

  $775,000

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

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229

  Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West.

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229
• 

  

  /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
• 

  

  /85

  $497,000

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229

  West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass

  Christine Pope MICHAEL SAUNDERS & COMPANY

  2309 Jessie Harbor Dr Unit 2402, Osprey, FL 34229
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /89

  $1,495,000

  Open Sun 12PM - 4PM

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 41 - 71, Page 2 of 2