Recently Sold Osprey, FL Homes

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  /2

  $452,500 Sold Aug 29, 2025

  • 1,574 Sq Ft
  • $287/SF
  • 257 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  784 Sarabay Rd, Osprey, FL 34229

  Welcome to Your Waterfront Villa in Osprey, Florida!Discover the ultimate seasonal retreat in this beautifully updated 2-bedroom, 2-bathroom single-story villa, designed for stress-free living. Nestled in a private 25-unit secluded community, this waterfront gem offers not only stunning views but also a lifestyle of unparalleled ease and simplicity.Key Features:Move in ready: Move in

  Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  Explore Osprey

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  /2

  $3,900,000 Sold Aug 27, 2025

  • 1,876 Sq Ft
  • $2,079/SF
  • 657 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  426 N Casey Key Rd, Osprey, FL 34229

  Gulf to Bay on North Casey Key – the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak floors add warmth and nostalgia throughout the home. A nicely updated kitchen overlooks the pool and bay. The entire second floor is dedicated to an oversized primary suite with a sitting room and

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  426 N Casey Key Rd, Osprey, FL 34229
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  /2

  $660,000 Sold Aug 26, 2025

  • 2,153 Sq Ft
  • $307/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  463 Park Trace Blvd, Osprey, FL 34229

  On an oversized lot with a breathtaking lake view, this open floor plan turnkey-furnished residence is designed for modern living. Recent upgrades include a new roof with a 15-year transferable warranty and a new water heater, ensuring peace of mind. Enter inside to high ceilings accented with crown molding, enhancing the home's spacious and refined atmosphere. At the heart of the home is a

  Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  463 Park Trace Blvd, Osprey, FL 34229
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  /2

  $470,000 Sold Aug 22, 2025

  • 2,166 Sq Ft
  • $217/SF
  • 80 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229

  Enjoy the best of coastal living in this spacious 2,166 sq. ft fully furnished townhouse condo, perfectly situated within walking distance of Casey Key and just steps from Casey Key Marina and Blackburn Point Park. This 15-acre waterfront park offers kayaking, fishing, a public boat ramp, and more. The thoughtfully designed first-floor master suite features a walk-in shower, a garden tub, and

  Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  /2

  $3,050,000 Sold Aug 15, 2025

  • 2,380 Sq Ft
  • $1,282/SF
  • 278 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1969

  5 N Casey Key Rd, Osprey, FL 34229

  HOME RUN DEAL YOU CAN'T AFFORD TO MISS! CASEY KEY GULF FRONT MOVE-IN READY FOR UNBELIEVABLE PRICE! REDUCED 900K! Iconic Gulf-front Mid-Century Modern gated residence on Casey Key embodies the true essence of casual coastal living, offering an unparalleled retreat for the soul. The moment you step through the door, a magical transformation takes place. Your senses awaken as you are immediately

  Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229
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  /2

  $247,000 Sold Aug 14, 2025

  • 1,325 Sq Ft
  • $186/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  121 Woodland Place Unit 121, Osprey, FL 34229

  Fabulous location for this FULLY FURNISHED, TURNKEY, two bedroom second floor condo in the Pine Run neighborhood. If you've been thinking of becoming a snowbird, you couldn't ask for more than this! Close to the iconic Casey Key Fish House Tiki Bar, the inter coastal, shopping, restaurants, main roads, and several beaches!! Located between Venice and Sarasota, you can easily enjoy both

  Pat Williams PAT WILLIAMS REALTY, LLC

  121 Woodland Place Unit 121, Osprey, FL 34229
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  /2

  $766,000 Sold Aug 08, 2025

  • 2,463 Sq Ft
  • $311/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  127 Park Trace Blvd, Osprey, FL 34229

  Absolutely Spectacular Lake-View Home in Osprey - with New ROOF and Upgrades throughout is priced to sell!This property boasts over $160,000 in enhancements, including a custom-designed luxury bath, bespoke mastercloset, renovated kitchen, porcelain flooring, remote-controlled blinds, plantation shutters, upgraded laundryfacilities, built-in outdoor grill, refinished pool w/new

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  127 Park Trace Blvd, Osprey, FL 34229
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  /2

  $975,000 Sold Aug 08, 2025

  • 2,344 Sq Ft
  • $416/SF
  • 161 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2016

  3904 Waypoint Ave, Osprey, FL 34229

  This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers. The home features a

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3904 Waypoint Ave, Osprey, FL 34229
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  /2

  $747,850 Sold Aug 08, 2025

  • 2,945 Sq Ft
  • $254/SF
  • 128 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1975

  424 Cezanne Dr, Osprey, FL 34229

  Welcome to your tropical oasis in ideally located, neighbor friendly Sorrento Shores! This spacious two-story, 4-bedroom, 4- bathroom pool home with oversized 3-car garage blends comfort, style, and functionality just minutes from Nokomis Beach near the confluence of South Creek and the Intercoastal Waterway. Located in an X flood zone (no flood insurance required), no CDD fees, and optional HOA,

  Christine Pope MICHAEL SAUNDERS & COMPANY

  424 Cezanne Dr, Osprey, FL 34229
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  /2

  $962,500 Sold Aug 07, 2025

  • 3,321 Sq Ft
  • $290/SF
  • 115 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  742 Shadow Bay Way, Osprey, FL 34229

  Welcome to Luxury Living in Rivendell! Nestled on a premium, private lot with serene lake and preserve views, this impeccably maintained, custom-built Arthur Rutenberg home offers elegance, comfort, and thoughtful design in every detail. Boasting 3,321 sq ft of refined living space, this residence features an open split floor plan, soaring ceilings, and abundant natural light throughout. The

  Reeny Kaney RE/MAX ALLIANCE GROUP

  742 Shadow Bay Way, Osprey, FL 34229
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  /2

  $1,015,000 Sold Aug 01, 2025

  • 3,912 Sq Ft
  • $259/SF
  • 11 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2002

  678 Clear Creek Dr, Osprey, FL 34229

  Looking for quality craftsmanship??? This exceptional home was built by US Homes, with a unique distinction — the original owner was the president of US Homes at the time of construction, personally overseeing every detail to ensure top-tier quality and craftsmanship throughout. This exquisitely remodeled 5-bedroom, 3-bath estate, nestled in one of Sarasota County's most desirable and serene

  Dena Olson EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /2

  $430,000 Sold Aug 01, 2025

  • 1,411 Sq Ft
  • $305/SF
  • 244 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  117 Villa Dr Unit 117, Osprey, FL 34229

  Let’s Go Fishing! Best Price in Sarasota County – Waterfront Villa with PRIVATE DOCK! Tenant in place! Welcome to your dream Florida lifestyle in Osprey, FL! This charming 2-bedroom waterfront villa is your perfect escape into the best of coastal living. Located in the peaceful, pet-friendly community of Sorrento Shores, this home offers direct access to the Gulf of Mexico, making it the

  Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  /2

  $645,000 Sold Jul 31, 2025

  • 2,223 Sq Ft
  • $290/SF
  • 9 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  673 Crane Prairie Way, Osprey, FL 34229

  Enjoy spectacular sunsets over a sweeping lake view the minute you walk through the door. This lovely Savannah model built by Lee Wetherington boasts three spacious bedrooms, three baths plus an office/flex room, making it the property for you and your family and guests. The primary suite has a sitting area that opens to the pool and lanai, two walk-in closets, and a large bath with double sinks,

  Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

  673 Crane Prairie Way, Osprey, FL 34229
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  /2

  $625,000 Sold Jul 26, 2025

  • 2,256 Sq Ft
  • $277/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 2001

  695 Rivendell Blvd, Osprey, FL 34229

  Welcome to 695 Rivendell Boulevard in Osprey, Florida – a beautifully maintained home offering comfort, style, and an unbeatable location. Just minutes from the Gulf Coast’s renowned beaches, shopping, and dining, this property features a host of recent upgrades designed for modern living. Hurricane protection includes a new garage door (2018) and Jansen electric roll-down and Bahama shutters

  Dan Henson DALTON WADE INC

  695 Rivendell Blvd, Osprey, FL 34229
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  /2

  $150,000 Sold Jul 25, 2025

  • 865 Sq Ft
  • $173/SF
  • 49 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1979

  107 Woodland Place Unit 107, Osprey, FL 34229

  This ground level condominium comes with a deeded carport and two storage closets. Enjoy a deck off the kitchen and a screened lanai that runs the length of the unit and is accessible from both the living area and bedroom. Both the half bath and primary bedroom suite have been recently remodeled with new flooring and fixtures. Washer and dryer hook-ups are located in an interior closet, so no

  Carla Rayman Kidd COLDWELL BANKER REALTY

  107 Woodland Place Unit 107, Osprey, FL 34229
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  /2

  $325,000 Sold Jul 24, 2025

  • 1,528 Sq Ft
  • $213/SF
  • 90 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  4236 Expedition Way Unit 106, Osprey, FL 34229

  FABULOUS, MODERN, FURNISHED 3 BEDROOM/2 BATHROOM/1 CAR GARAGE CONDO in desirable Bay Street Village. This second story (walk-up) is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include a designer kitchen with cherry cabinets, crown molding, granite countertops, IMPACT WINDOWS, tile roof, paver

  Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
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  /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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  /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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  /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

  $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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  /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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  /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
• 

  /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
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  /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
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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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  /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
• 

  /2

  $788,000 Sold Jun 27, 2025

  • 2,266 Sq Ft
  • $348/SF
  • 10 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  521 Habitat Blvd, Osprey, FL 34229

  Welcome to this exquisite Lee Wetherington-built residence in Willowbend, where high-end finishes and meticulous attention to detail create an enchanting living experience. This light-filled home features a great room floor plan, anchored by a stunning custom fireplace surrounded by elegant cabinetry. The residence has undergone extensive remodeling, showcasing timeless appeal and luxury at every

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  521 Habitat Blvd, Osprey, FL 34229
• 

  /2

  $640,000 Sold Jun 20, 2025

  • 2,590 Sq Ft
  • $247/SF
  • 119 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1999

  455 Park Trace Blvd, Osprey, FL 34229

  CURRENTLY BEST VALUE IN OSPREY! Premium Lakefront lot with Stunning Views from Nearly Every Room! Discover the perfect blend of comfort, convenience, and breathtaking views in this Park Trace Estates beauty. This home features a NEW ROOF (Jan. 2024,) New Energy efficient A/C (May 2024) and brand new pool pump and motor (March 2025), AND...newly refurbished patio and pool deck in April. Ideally

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  455 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  $395,000 Sold Jun 16, 2025

  • Land
  • 0.52 Acre
  • $759,615 per Acre

  • 30 Days On Market

  109 Burney Rd, Osprey, FL 34229

  Build your dream home on this HALF ACRE lot situated on a quiet dead-end street with no neighboring homes on 3 sides. This property offers a rare sense of seclusion and tranquility, perfect for those seeking a peaceful retreat. The property includes a well-maintained home with two bedrooms, one and a half bathrooms, an outdoor shower, three large sheds, two extra-long driveways, perfect for

  Lori Madden MANGROVE REALTY ASSOCIATES

  109 Burney Rd, Osprey, FL 34229
• 

  /2

  $395,000 Sold Jun 16, 2025

  • 714 Sq Ft
  • $553/SF
  • 50 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1959

  109 Burney Rd, Osprey, FL 34229

  Discover this hidden gem—a charming Florida/Craftsman bungalow nestled on a spacious half-acre lot, thoughtfully landscaped for ultimate privacy and serenity. Situated on a quiet dead-end street with no neighboring homes on 3 sides, this property offers a rare sense of seclusion and tranquility, perfect for those seeking a peaceful retreat. This well-maintained home features two bedrooms, one and

  Lori Madden MANGROVE REALTY ASSOCIATES

  109 Burney Rd, Osprey, FL 34229
• 

  /2

  $720,000 Sold Jun 16, 2025

  • 2,320 Sq Ft
  • $310/SF
  • 130 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  518 Luminary Blvd, Osprey, FL 34229

  Discover the perfect blend of comfort and sophistication in this meticulously maintained home located in the highly desirable Willowbend community. The striking architecture of the Ashley floor plan, complete with a rare three-car garage with epoxy floor, enhances the property’s curb appeal. Enjoy peace of mind with hurricane impact-rated doors, windows and sliders throughout the residence. Step

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  518 Luminary Blvd, Osprey, FL 34229
• 

  /2

  $725,000 Sold Jun 13, 2025

  • 2,678 Sq Ft
  • $271/SF
  • 75 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  608 Crane Prairie Way, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Exceptional Opportunity on this Newly Priced Gem with stunning views and privacy! Discover your dream home in this stunning 2,678 square foot Wyndham model by Lee Wetherington, one of the largest in the maintenance-free community of Willowbend in Osprey. The owner has added improvements in excess of $150K since their purchase and has been lovingly

  Linda Williams GULF SHORES REALTY

  608 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  $235,000 Sold Jun 13, 2025

  • 1,223 Sq Ft
  • $192/SF
  • 144 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  109 Woodland Place, Osprey, FL 34229

  Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community in Osprey, Florida. This charming 2-bedroom, 2-bathroom condominium offers 1,223 square feet of thoughtfully designed living space, seamlessly blending comfort with the beauty of its environment. As you enter, you’ll be greeted by soaring ceilings and an open floor plan that

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  109 Woodland Place, Osprey, FL 34229
• 

  /2

  $685,000 Sold Jun 12, 2025

  • 2,203 Sq Ft
  • $311/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2000

  385 N Point Rd Unit 503, Osprey, FL 34229

  Experience luxury coastal living in this 5th-floor condo, offering breathtaking water and Preserve views that rival those of higher floors. This residence in Meridian at The Oaks Preserve features 3 bedrooms, 3 full baths, and a dining room, all enhanced with new furnishings. Offered turnkey, all it needs is for you to move in and start living a carefree lifestyle on Florida’s gorgeous Gulf

  Steve Abbe COLDWELL BANKER REALTY

  385 N Point Rd Unit 503, Osprey, FL 34229
• 

  /2

  $1,700,000 Sold Jun 12, 2025

  • 2,315 Sq Ft
  • $734/SF
  • 108 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1972

  525 S Shore Dr, Osprey, FL 34229

  This redesigned mid-century styled 3-bedroom Bayfront home has been fully remastered with entertaining in mind. The stunning outdoor oasis says it all, with a panoramic view pool cage, a large, covered area, outdoor kitchen, and an amazing pool and spa featuring a stone waterfall and propane-fueled fire sconces. The pool cage was recently rescreened with no see um screen. Inside, the split

  Andree Huffine COLDWELL BANKER REALTY

  525 S Shore Dr, Osprey, FL 34229
• 

  /2

  $3,525,000 Sold Jun 06, 2025

  • 5,279 Sq Ft
  • $668/SF
  • 124 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2007

  275 Lookout Point Dr, Osprey, FL 34229

  This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  275 Lookout Point Dr, Osprey, FL 34229
• 

  /2

  $640,000 Sold Jun 04, 2025

  • 2,234 Sq Ft
  • $286/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  519 Habitat Blvd, Osprey, FL 34229

  This exquisite three-bedroom, three-bath-plus-den home by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. The Savannah floor plan is a rare great room plan with one of the few natural gas fireplaces in the neighborhood. This is the focal point of the home with stacked flagstone and a beautiful mantel flanked in shelving. The residence features an

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  519 Habitat Blvd, Osprey, FL 34229
• 

  /2

  $1,197,000 Sold May 30, 2025

  • 3,321 Sq Ft
  • $360/SF
  • 20 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1991

  223 Saint James Park, Osprey, FL 34229

  Luxury Clubside Living at The Oaks – featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf course views, this beautifully upgraded home offers 3,321 sq ft of refined living space in one of Sarasota’s most exclusive communities. You’re

  John Hockenberry RE/MAX ALLIANCE GROUP

  223 Saint James Park, Osprey, FL 34229
• 

  /2

  $904,900 Sold May 30, 2025

  • 2,705 Sq Ft
  • $335/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  336 Pine Ranch Rd E, Osprey, FL 34229

  Nestled on a rare one-acre private oasis, this stunning lakefront home in Osprey offers the perfect blend of tranquility and convenience. With mature landscaping, majestic pine trees, and abundant wildlife, this is a true sanctuary—yet you're just minutes from Pine View School (Ranked #18 in the nation), Siesta Key Beach, The Legacy Trail, and US-41. Near I-75, centrally located between Venice

  Marco Guadagnini PREFERRED SHORE LLC

  336 Pine Ranch Rd E, Osprey, FL 34229
• 

  /2

  $285,000 Sold May 30, 2025

  • 1,255 Sq Ft
  • $227/SF
  • 112 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  7102 Jessie Harbor Dr, Osprey, FL 34229

  Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature and well groomed grounds you’ll park in your private under building parking space near your own large secured storage unit. Elevators take you up to Unit 71 where you’ll immediately appreciate the opportunity to utilize the covered outdoor space at the condo entrance to enjoy

  Chris Rankin RE/MAX PALM REALTY

  7102 Jessie Harbor Dr, Osprey, FL 34229

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