Osprey, FL Homes

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  $42,500

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 10.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
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  $600,000 Sold Apr 18, 2025

  • 2,887 Sq Ft
  • $208/SF
  • 24 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1995

  402 Pine Ranch Rd E, Osprey, FL 34229

  LLocated 1-2 mile from the legacy trail off Bay St. in Osprey. Built on one acre in 1995. This is a 3-bedroom 3.5 bath home that has a lot of potential. The large office in the front of the home could be made into a 4th bedroom. The family room has a fireplace, built-in shelving and has a view of the pool. The pool bath is behind the family room with direct access to the pool. The master suite

  Ronnie Caron CARON REALTY INC

  402 Pine Ranch Rd E, Osprey, FL 34229
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  /52

  Est $2,368,547 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 5,521 Sq Ft

  134 Marys Chapel Ct, Osprey, FL 34229

  134 Marys Chapel Ct, Osprey, FL 34229
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  /8

  $44,000

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229

  Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota CountySecure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by

  Rick Bumbaca AZZURRO REALTY

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229
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  $650,000 Sold Apr 18, 2025

  • 2,431 Sq Ft
  • $267/SF
  • 113 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  610 Pine Ranch Rd E, Osprey, FL 34229

  Price Reduced on this Magnificent three bedroom, two bath home with den, heated pool, fenced yard for privacy in Bay Oaks Estates in Osprey. This fantastic, well maintained home has it all including a LOW annual fee of $270. Features include an updated kitchen with large farmer sink, quartz counters, Bosch Range with stainless hood, Bosch dishwasher, Samsung Refrigerator with plenty of storage,

  Kim Klee COLDWELL BANKER REALTY

  610 Pine Ranch Rd E, Osprey, FL 34229
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  /41

  Est $578,443 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  506 Oak Bay Dr, Osprey, FL 34229

  506 Oak Bay Dr, Osprey, FL 34229
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  $725,000

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet and offers stunning, unobstructed vistas of the intracoastal waterways and Gulf of Mexico. Located within a gated, amenity-rich community, this condo features an open floor plan with high ceilings, a spacious kitchen, and a living area that seamlessly blends indoor comfort with

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
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  $1,050,000 Sold Apr 16, 2025

  • 2,871 Sq Ft
  • $366/SF
  • 70 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  247 Keel Way, Osprey, FL 34229

  No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located in an X flood zone! This beautiful home located in "west of the trail", Southbay Yacht and Racquet Club is a very sought after location. One of the few communities with it's own marina and very reasonable dock rental fees only available to homeowners in the community. This home

  Pat Williams PAT WILLIAMS REALTY, LLC

  247 Keel Way, Osprey, FL 34229
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  /79

  Est $1,463,568 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,521 Sq Ft

  1236 Yacht Harbor Dr, Osprey, FL 34229

  1236 Yacht Harbor Dr, Osprey, FL 34229
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  /43

  $689,000

  • 4 Beds
  • 2 Baths
  • 2,145 Sq Ft

  819 Shadow Bay Way, Osprey, FL 34229

  A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  819 Shadow Bay Way, Osprey, FL 34229
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  /2

  $385,000 Sold Apr 16, 2025

  • 1,346 Sq Ft
  • $286/SF
  • 244 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  329 Bay Vista Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Come see this charming house in Osprey It features 2 bedrooms , 2 baths and a 2 car garage .The main bedroom has a sitting room. The kitchen has been updated with white cabinets with soft close drawers, granite countertops, stainless steel refrigerator and dishwasher. Save on electricity with the fully owned solar panel system. The entire yard is

  Colette Jay HORIZON REALTY INTERNATIONAL

  329 Bay Vista Ave, Osprey, FL 34229
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  /45

  Est $2,830,251 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,202 Sq Ft

  349 Yacht Harbor Dr, Osprey, FL 34229

  349 Yacht Harbor Dr, Osprey, FL 34229
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  /92

  $5,700,000

  • 6 Beds
  • 5 Baths
  • 4,893 Sq Ft

  622 Bayshore Dr, Osprey, FL 34229

  ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle

  Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  622 Bayshore Dr, Osprey, FL 34229
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  $945,000 Sold Apr 15, 2025

  • 2,677 Sq Ft
  • $353/SF
  • 4 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  128 Sea Anchor Dr, Osprey, FL 34229

  New to the market, your dream home awaits in the exclusive private marina community of Southbay Yacht and Racquet Club. For boating enthusiasts, this is the opportunity you’ve been waiting for! In the sought-after Southbay Yacht and Racquet Club, this stunning residence combines spacious design with the best of Florida living, just steps from your boat. Imagine waking up and stepping out onto

  Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

  128 Sea Anchor Dr, Osprey, FL 34229
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  /50

  Est $379,330 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft

  1821 Highland Rd, Osprey, FL 34229

  1821 Highland Rd, Osprey, FL 34229
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  /24

  $624,700

  • Land
  • 0.34 Acre
  • $1,837,353 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

  Matthew Charland LLC GULF SHORES REALTY

  458 N Shore Dr, Osprey, FL 34229
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  $390,000 Sold Apr 15, 2025

  • 1,334 Sq Ft
  • $292/SF
  • 21 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  441 N Shore Dr, Osprey, FL 34229

  Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry

  Dawn Barnett EXIT KING REALTY

  441 N Shore Dr, Osprey, FL 34229
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  /86

  Est $1,613,241 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,087 Sq Ft

  435 E MacEwen Dr, Osprey, FL 34229

  435 E MacEwen Dr, Osprey, FL 34229
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  /41

  $164,900

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft

  170 Edgewood Dr, Osprey, FL 34229

  YOUR PERFECT FLORIDA RETREAT AWAITS.... Imagine spending your winter days in a swimming pool or in the warm waters and beautiful sands of Florida Gulf Coast beaches. This pristine 2 Bed, 2 Bath home located in the Arbors Mobile Park has been meticulously maintained and has many upgrades and extras. Open plan kitchen has dining area and built-in china cabinet. The master bedroom is ensuite and

  Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
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  $1,160,000 Sold Apr 15, 2025

  • 1,787 Sq Ft
  • $649/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  131 Tina Island Dr, Osprey, FL 34229

  Welcome to your dream waterfront oasis! This exquisite 3-bedroom, 2-bathroom residence offers unparalleled water views and mesmerizing sunsets from the expansive pool deck. The generous outdoor living area is perfect for hosting gatherings or enjoying peaceful moments by the canal. The thoughtfully designed split-bedroom layout ensures privacy, making it ideal for accommodating guests or family

  Sarah McGuire WHITE SANDS REALTY GROUP FL

  131 Tina Island Dr, Osprey, FL 34229
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  /69

  Est $657,865 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,144 Sq Ft

  521 Bayshore Dr, Osprey, FL 34229

  521 Bayshore Dr, Osprey, FL 34229
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  /35

  $310,000

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

  4267 Expedition Way, Osprey, FL 34229

  Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions. This

  Judi Cipollina COLDWELL BANKER REALTY

  4267 Expedition Way, Osprey, FL 34229
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  $700,000 Sold Apr 15, 2025

  • 2,504 Sq Ft
  • $280/SF
  • 69 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  521 Luminary Blvd, Osprey, FL 34229

  This stunning Lee Wetherington home, in the prestigious Willowbend community of Osprey, showcases the natural beauty of Florida through its beautifully designed Stanford, rarely available floor plan. Home has a 22-kilowatt whole-house generator. Set against the backdrop of a sparkling lake, the residence features a great room, dining area, kitchen, dinette, owner’s suite all benefiting from one

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  521 Luminary Blvd, Osprey, FL 34229
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  /96

  Est $1,662,386 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,857 Sq Ft

  627 N MacEwen Dr, Osprey, FL 34229

  627 N MacEwen Dr, Osprey, FL 34229
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  /8

  $27,900

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 5, Osprey, FL 34229

  Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 370 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 5, Osprey, FL 34229
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  $879,352 Sold Apr 15, 2025

  • 1,937 Sq Ft
  • $454/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Under Construction. Photos are a representation of multiple floor plans in the building. Watch the most breathtaking sunsets from your private extra-large, screened-in balcony as you look out across the bay to the barrier island of Casey Key! Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. This

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229
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  Est $1,835,187 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,368 Sq Ft

  451 E MacEwen Dr, Osprey, FL 34229

  451 E MacEwen Dr, Osprey, FL 34229
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  /13

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  4428 Conchfish Ln, Osprey, FL 34229

  Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

  Mariana Georgieva HORIZON REALTY INTERNATIONAL

  4428 Conchfish Ln, Osprey, FL 34229
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  $832,000 Sold Apr 14, 2025

  • 1,988 Sq Ft
  • $419/SF
  • 178 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  14041 Bellagio Way Unit 313, Osprey, FL 34229

  Welcome to the highly desirable community of The Villas at Osprey Harbor! This light and bright end unit with a private entrance is loaded with recent, tasteful updates including a fully renovated kitchen in 2022 with high end rift cut white oak custom cabinetry and a quartz breakfast bar, induction stove, updated baths, 24-by-24 porcelain tile, lighting, fans, fresh paint throughout, a coffee

  Megan George PREMIER SOTHEBYS INTL REALTY

  14041 Bellagio Way Unit 313, Osprey, FL 34229
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  Est $240,709 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 858 Sq Ft

  110 Oak St, Osprey, FL 34229

  110 Oak St, Osprey, FL 34229
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  /75

  $175,000

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

  137 Woodland Place, Osprey, FL 34229

  Unbelievable!!! A 2-bedroom/2-bathroom, West of Trail condo for under $200,000! Come home to this warm, cozy and charming unit and enjoy a cup of tea on your tranquil and private outside deck, nestled in a wooded, West of Trail paradise! The condo is surrounded by a backdrop of nature and you can enjoy the outdoors on three balconies which is wonderfully unique! The unit features generous room

  Priscilla Adams COMPASS FLORIDA LLC

  137 Woodland Place, Osprey, FL 34229
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  /2

  $275,000 Sold Apr 11, 2025

  • 900 Sq Ft
  • $306/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  208 Pennsylvania Ave, Osprey, FL 34229

  PRICED to SELL! Incredible Opportunity, Don\'t miss this one! Nice 3Br 2Ba single family home on large fenced corner lot in Osprey, Florida near Venice Beach. NO HOA! Large lot with plenty of space for additions, RV or Boat parking, swimming pool, etc. One of the best deals in the area! Turn-key and ready to move in, New paint

  Stephen Hachey FLAT FEE MLS REALTY

  208 Pennsylvania Ave, Osprey, FL 34229
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  /11

  Est $842,391 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft

  226 Saint James Park, Osprey, FL 34229

  226 Saint James Park, Osprey, FL 34229
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  /60

  $1,279,000

  • 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. 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 fridge. Large

  Matthew Lewis BRIGHT REALTY

  1527 Buoy Ln, Osprey, FL 34229
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  $925,000 Sold Apr 10, 2025

  • 2,166 Sq Ft
  • $427/SF
  • 31 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Under Construction. Under construction. The photos are a representation of multiple floor plans in the building. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. The gated, 12-acre resort-style community is nestled on the water’s edge of Little Sarasota Bay in Osprey. The final waterfront building

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229
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  /70

  Est $1,752,268 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,551 Sq Ft

  337 Passage Way, Osprey, FL 34229

  337 Passage Way, Osprey, FL 34229
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  /89

  $1,150,000

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

  401 N Point Rd Unit 504, Osprey, FL 34229

  FULLY UPDATED ~ WATER VIEWS ~ PRIVATE 2 CAR GARAGE ~ OFFICE/4TH BEDROOM OPTION ~ The eye of an artist and perfected skill of a craftsman created this spacious, expertly designed residence. From the moment the elevator doors open to the private foyer, you'll notice every fine detail in this home was carefully thought out and executed, while the splendor of nature and water creates the backdrop

  Mary Elizabeth Mock COLDWELL BANKER REALTY

  401 N Point Rd Unit 504, Osprey, FL 34229
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  /2

  $400,000 Sold Apr 08, 2025

  • 1,574 Sq Ft
  • $254/SF
  • 115 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  4239 Expedition Way, Osprey, FL 34229

  NEW PRICE AND PRICED TO SELL - THE ONLY AVAILABLE 2 CAR GARAGE UNIT LISTED IN THE COMMUNITY! Welcome to Bay Street Village, a highly sought-after gated condominium community in the heart of Osprey. This rarely available FIRST FLOOR, EXTENDED 2-car garage condo offers plenty of space for vehicles and gear, making it ideal for those with an active lifestyle. The beautiful home is being sold

  Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
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  /24

  Est $849,361 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  130 N Creek Ln, Osprey, FL 34229

  130 N Creek Ln, Osprey, FL 34229
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  /36

  $444,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  352 Glenwood Ave, Osprey, FL 34229

  Beautifully Maintained 3-Bedroom Home with No HOA or Deed RestrictionsWelcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining.Enjoy

  Kano Keller WHITE SANDS REALTY GROUP FL

  352 Glenwood Ave, Osprey, FL 34229

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