Osprey, FL Homes

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  /68

  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  /39

  $4,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
• 

  

  /2

  $35,000 Sold Jul 22, 2025

  • 62 Days On Market

  • Built 2006

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village—hurricane-protected dry storage with top-tier amenities! This rarely available top-level slip means no boats dripping on yours and offers hassle-free storage in one of Sarasota County’s most convenient locations. Keep your boat safe from Florida’s unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229
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  /46

  Est $588,908 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2007 Cordes St, Osprey, FL 34229

  2007 Cordes St, Osprey, FL 34229
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  /68

  $998,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft

  766 Shadow Bay Way, Osprey, FL 34229

  Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening

  Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /9

  $2,300 per month

  • 3 Beds
  • 1.5 Baths
  • 1,173 Sq Ft
  • House for Rent

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
• 

  /2

  $1,050,000 Sold Jul 22, 2025

  • 2,531 Sq Ft
  • $415/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  142 Dory Ln, Osprey, FL 34229

  Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  142 Dory Ln, Osprey, FL 34229
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  /5

  Not Listed For Sale

  0 N Point Rd Unit A11454780, Osprey, FL 34229

  0 N Point Rd Unit A11454780, Osprey, FL 34229
• 

  

  /32

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  /39

  $4,200 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
• 

  /2

  $760,000 Sold Jul 16, 2025

  • 3,091 Sq Ft
  • $246/SF
  • 158 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  790 Shadow Bay Way, Osprey, FL 34229

  Brand New Tile Roof March 2025. Experience the ultimate in serene living within the picturesque Woodlands of Rivendell, where this stunning residence seamlessly combines the beauty of nature with modern comforts. Bordered by a preserve at the rear and flanked by mature trees across the street, it offers the perfect sanctuary for those seeking tranquility amidst lush greenery. The curb appeal is

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  790 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $316,247 Not Listed For Sale

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

  4219 Frontier Ln Unit 105, Osprey, FL 34229

  4219 Frontier Ln Unit 105, Osprey, FL 34229
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  /38

  $815,000

  • 3 Beds
  • 2 Baths
  • 2,443 Sq Ft

  901 Reflection Way, Osprey, FL 34229

  LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

  Mark Lyda GENEROUS PROPERTY

  901 Reflection Way, Osprey, FL 34229
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  /17

  $3,999 per month

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • House for Rent

  510 Latitude Ln, Osprey, FL 34229

  Custom, Lee Wetherington home with a private heated pool in the sought after, maintenance free community of Willow Bend. Located close to Pineview School, Legacy Trail, Oscar Scherer Park and our world-famous beaches. This home features volume tray ceilings with lots of natural light, natural gas cooking, crown molding, built in features and indoor laundry. The large master suite features double

  Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
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  /2

  $145,000 Sold Jul 15, 2025

  • 23 Days On Market

  • Built 2006

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village hurricane-protected dry storage with top-tier amenities! This rarely available slip 1st level T-Top slip can fit boats up to 12 ft in height and offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 27, Osprey, FL 34229
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  /24

  Est $306,563 Not Listed For Sale

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

  4224 Expedition Way Unit 105, Osprey, FL 34229

  4224 Expedition Way Unit 105, Osprey, FL 34229
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  /62

  $965,000

  • 2 Beds
  • 2 Baths
  • 2,310 Sq Ft

  13 Bayhead Ln, Osprey, FL 34229

  **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

  Mark Lyda GENEROUS PROPERTY

  13 Bayhead Ln, Osprey, FL 34229
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  /35

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229

  One or more photo(s) has been virtually staged. ***Price Reduced****Annual Rental. This newly constructed 3rd floor condo is available for immediate occupancy at Hidden Bay in Osprey. This gorgeous 3 Bedroom PLUS a Home Office is light, bright and very spacious! Wood and tile floors throughout- NO CARPETING! The Primary suite features 2 walk-in closets, sliding glass doors leading to the lanai

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229
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  /2

  $1,405,000 Sold Jul 11, 2025

  • 3,699 Sq Ft
  • $380/SF
  • 128 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 1992

  282 Shell Midden Ct, Osprey, FL 34229

  One or more photo(s) has been virtually staged. It is rare to find such an incredible combination of privacy and spectacular views as you will find in this 3 bedroom, 4.5 bath home. Located on a quiet dead-end street in The Oaks Bayside, the traditional design marries beauty with functionality. Step inside and you will be greeted by light-filled space with classic motif. Large windows flood

  Steve Abbe COLDWELL BANKER REALTY

  282 Shell Midden Ct, Osprey, FL 34229
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  /4

  Est $55,568 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
• 

  

  /79

  $1,450,000

  • 4 Beds
  • 3.5 Baths
  • 3,464 Sq Ft

  402 Walls Way, Osprey, FL 34229

  Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedroom plus den/office, 3.5-bath home, built in 2014 by Todd Johnson Homes, blends country modern style with refined sophistication. Situated on an oversized .64-acre corner lot, this courtyard-style residence is designed for effortless Florida living. Step through grand double wood doors into an inviting space

  Steve Abbe COLDWELL BANKER REALTY

  402 Walls Way, Osprey, FL 34229
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  /87

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

  This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you step inside the

  Chrissie Cummings JENNETTE PROPERTIES INC

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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  /2

  $505,000 Sold Jul 08, 2025

  • 2,302 Sq Ft
  • $219/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  622 Pine Ranch Rd E, Osprey, FL 34229

  Significant price drop on this fabulous Turnkey, Tastefully Decorated Florida Pool home has everything you need to enjoy the Gulf Coast lifestyle. This three bedroom two bath home (plus a Den) sits on an oversized corner lot with a vinyl privacy fence and a side gate where you can store your water toys for your adventures on the Intercoastal Waterway. Lounge by the pool in your screened Lanai,

  Terri Persing PARADISE EXCLUSIVE INC

  622 Pine Ranch Rd E, Osprey, FL 34229
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  /12

  Est $25,146 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
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  /78

  $1,095,000

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft

  820 Placid Lake Dr, Osprey, FL 34229

  Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh

  Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
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  /43

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 2,374 Sq Ft
  • Condo for Rent

  14041 Bellagio Way Unit 218, Osprey, FL 34229

  Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from Midnight Pass beach, Snake Island and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space with breath taking harbor and sunset views from every room. Designed with both comfort and style

  Kelli Eggen COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 218, Osprey, FL 34229
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  /2

  $1,500,000 Sold Jul 08, 2025

  • 3,572 Sq Ft
  • $420/SF
  • 76 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  269 Pine Ranch Trail, Osprey, FL 34229

  One or more photo(s) has been virtually staged. This magnificent modern manse, with 4 bedrooms and 3.5 baths, literally has everything you could dream of to make a home complete, ALL OF IT NEW! Located in Pine Ranch, a community of single family homes with 1-5 acres of land, you will not find a more stately, spacious home, completely updated and ready for you to live out your Florida dreams.

  Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
• 

  

  /50

  Est $566,711 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2006 Preymore St, Osprey, FL 34229

  2006 Preymore St, Osprey, FL 34229
• 

  

  /61

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft

  3603 N Point Rd Unit 702, Osprey, FL 34229

  **MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 702, Osprey, FL 34229
• 

  

  /25

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Townhouse for Rent

  184 Explorer Dr, Osprey, FL 34229

  The unit is available for rent from September 15 till December 25 ,2025.The minimum rental period is 2 months. The monthly rent is $1995. The tenant is responsible for electricity and internet costs. NO PETS! INCLUDED IN THE LEASE : Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close

  Claudia Dybala DALTON WADE INC

  184 Explorer Dr, Osprey, FL 34229
• 

  /2

  $650,000 Sold Jul 03, 2025

  • 2,100 Sq Ft
  • $310/SF
  • 246 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1997

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229

  This beautiful 3 bed, 3 full ensuite baths and a 3 car garage home in the heart of Osprey in the desirable waterfront gated Hidden Bay Community. Come home to your own hidden gem and enjoy SPECTACULAR unobstructed views of Sarasota’s Intracoastal Waterway, also known as Little Sarasota Bay, and preserve. Complete with updated PGT WINGUARD IMPACT WINDOWS AND DOORS installed in 2018. This

  Linda Scheller COLDWELL BANKER REALTY

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229
• 

  

  /17

  Est $308,793 Not Listed For Sale

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

  4247 Expedition Way Unit 103, Osprey, FL 34229

  4247 Expedition Way Unit 103, Osprey, FL 34229
• 

  

  /80

  $2,995,000

  • 4 Beds
  • 4 Baths
  • 4,359 Sq Ft

  662 Fernwalk Ln, Osprey, FL 34229

  **FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is

  Mark Lyda GENEROUS PROPERTY

  662 Fernwalk Ln, Osprey, FL 34229
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  /33

  $3,695 per month

  • 2 Beds
  • 3.5 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  60 Bishops Court Rd Unit 114, Osprey, FL 34229

  This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

  Heidi Thompson STRINGER MANAGEMENT INC

  60 Bishops Court Rd Unit 114, Osprey, FL 34229
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  /2

  $85,000 Sold Jul 01, 2025

  • 336 Days On Market

  • Built 2006

  570 Blackburn Point Rd Unit 7, Osprey, FL 34229

  Rarely available 1st level boat rack 12.5 H X 10 W X 28 L.Marina has a restaurant bar and bait and tackle shop next door.Fuel onsite and a friendly staff.

  Troy Gager BRIGHT REALTY

  570 Blackburn Point Rd Unit 7, Osprey, FL 34229
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  /39

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  169 Edgewood Dr, Osprey, FL 34229

  169 Edgewood Dr, Osprey, FL 34229
• 

  

  /100

  $1,750,000

  • 3 Beds
  • 3.5 Baths
  • 3,872 Sq Ft

  422 Blue Garden Ln, Osprey, FL 34229

  A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal

  Steve Abbe COLDWELL BANKER REALTY

  422 Blue Garden Ln, Osprey, FL 34229
• 

  

  /36

  $7,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft
  • Townhouse for Rent

  101 Woodland Place, Osprey, FL 34229

  Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! West of the Trail, Pine Run is a waterfront tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed Kitchen is

  Patrice Ivan WAGNER REALTY

  101 Woodland Place, Osprey, FL 34229
• 

  /2

  $1,285,000 Sold Jun 30, 2025

  • 3,029 Sq Ft
  • $424/SF
  • 204 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2001

  393 N Point Rd Unit 801, Osprey, FL 34229

  Rare in every way, this 3 bedroom, 3 bath penthouse, with private two car garage, is only one of six units in Meridian that enjoys this incredible floor plan. The elegant interior is punctuated by SPECTACULAR VIEWS. This residence provides everything you could desire for a luxury lifestyle in Coastal Florida. A former model, it has been lovingly maintained, and beautifully updated. From the

  Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 801, Osprey, FL 34229
• 

  

  /27

  Est $370,683 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  4260 Expedition Way Unit 4260, Osprey, FL 34229

  4260 Expedition Way Unit 4260, Osprey, FL 34229

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