Osprey, FL Homes

• 

  

  

  /6

  $34,500

  • 2 Beds
  • 1 Bath

  124 Happy Haven Dr Unit 8, Osprey, FL 34229

  Make your new home in Happy Haven, a well-maintained, professionally managed manufactured home community! Own a 1966, 1bed/1bath, 564 sqft. home in a great neighborhood. This one won't be on the market for long! Take advantage of this offer now and live in one of the state's most attractive areas. Let us show you around the place! Call and schedule a viewing today! Financing information available.

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 8, Osprey, FL 34229
• 

  

  /2

  $315,000 Sold Apr 24, 2025

  • 1,092 Sq Ft
  • $288/SF
  • 147 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  214 Patterson Ave, Osprey, FL 34229

  Welcome to your dream home in the enchanting village of Osprey! This inviting 3-bedroom, 2-bathroom block home is nestled on a tranquil street, surrounded by lush landscaped gardens. Designed with comfort and functionality in mind, the open-plan living and dining area provides an ideal space for gatherings, with a clear view into the fully remodeled kitchen. Whether cooking or entertaining, the

  Lisa Bouck, PA RE/MAX ALLIANCE GROUP

  214 Patterson Ave, Osprey, FL 34229
• 

  

  

  /31

  Not Listed For Sale

  0 Webb St Unit A4546155, Osprey, FL 34229

  0 Webb St Unit A4546155, Osprey, FL 34229
• 

  

  

  /61

  $325,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  116 Navigation Cir Unit 106, Osprey, FL 34229

  Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

  Pan Steele, GRI COLDWELL BANKER REALTY

  116 Navigation Cir Unit 106, Osprey, FL 34229
• 

  

  /2

  $880,000 Sold Apr 23, 2025

  • 2,045 Sq Ft
  • $430/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1237 Flying Bridge Ln, Osprey, FL 34229

  A Southbay Yacht & Racquet Club beauty! This home has been given meticulous care and offers an abundance of updates and upgrades. Popular Southbay community features a boating marina on the Inter coastal Waterway, making this one of the most sought after locations west of the trail! This airy and open floorplan is sure to please! There are so many delightful updates and improvements, I'll try to

  Pat Williams PAT WILLIAMS REALTY, LLC

  1237 Flying Bridge Ln, Osprey, FL 34229
• 

  

  /25

  Est $251,686 Not Listed For Sale

  13 Bay Ave, Osprey, FL 34229

  13 Bay Ave, Osprey, FL 34229
• 

  

  /14

  $234,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  238 Palm Air Dr, Osprey, FL 34229

  AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais

  John Alexander FINE PROPERTIES

  238 Palm Air Dr, Osprey, FL 34229
• 

  /2

  $807,000 Sold Apr 22, 2025

  • 2,112 Sq Ft
  • $382/SF
  • 244 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  124 Tina Island Dr, Osprey, FL 34229

  ***Amazing waterfront opportunity*** One of the lowest priced canal front properties between Sarasota and Venice*** This great waterfront location is in desirable Sorrento Shores with a new dock on a wide canal sitting on a large lot with great views This 3 bedroom 2 bath split plan has a large living/dining area and a separate office space. The kitchen area has a separate seating area with a

  Glenn Davis COLDWELL BANKER SARASOTA CENT.

  124 Tina Island Dr, Osprey, FL 34229
• 

  

  /21

  Est $326,418 Not Listed For Sale

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

  4192 Expedition Way, Osprey, FL 34229

  4192 Expedition Way, Osprey, FL 34229
• 

  

  /62

  $785,500

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft

  523 Habitat Blvd, Osprey, FL 34229

  In the Lee Wetherington built community of Willowbend is a stunning home. This enchanting residence is bordering a sparkling lake with curb appeal emphasized by lush landscaping and a paver accented driveway. This quality-built home is the desirable Ashley II floor plan, with an oversized 23-by-19 garage. Every detail in this home is addressed with remarkable style including double-door entry,

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
• 

  /2

  $245,000 Sold Apr 21, 2025

  • 1,316 Sq Ft
  • $186/SF
  • 103 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  225 Woodland Dr, Osprey, FL 34229

  This completely remodeled, GROUND LEVEL, 2/2 condo is available in a charming West of Trail community (but not in a flood zone) and is the hidden gem you've been looking for! Step inside and be captivated by artistic elegance. This home has been thoughtfully updated and features a new HVAC system in 2023, a kitchen remodel in 2023 including sleek new appliances (including an induction cooktop),

  Priscilla Adams COMPASS FLORIDA LLC

  225 Woodland Dr, Osprey, FL 34229
• 

  

  /33

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  155 Edgewood Dr, Osprey, FL 34229

  155 Edgewood Dr, Osprey, FL 34229
• 

  

  /4

  $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
• 

  /2

  $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
• 

  

  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  168 Edgewood Dr, Osprey, FL 34229

  168 Edgewood Dr, Osprey, FL 34229
• 

  

  /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
• 

  /2

  $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
• 

  

  /60

  Est $378,870 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  4129 Frontier Ln Unit 104, Osprey, FL 34229

  4129 Frontier Ln Unit 104, Osprey, FL 34229
• 

  

  /34

  $800,000 Open Sun 8AM - 7PM

  • 5 Beds
  • 4 Baths
  • 3,395 Sq Ft

  851 Placid Lake Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Fresh Interior Paint, Fresh Exterior Paint, Partial flooring replacement in some areas. Discover a bright interior tied together with a neutral color palette. You'll love cooking in this kitchen, complete with a spacious center island and a sleek backsplash. Head to the spacious primary suite with

  Karen Albright OPENDOOR BROKERAGE LLC

  851 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $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
• 

  

  /3

  Est $230,500 Not Listed For Sale

  436 Glenwood Ave, Osprey, FL 34229

  436 Glenwood Ave, Osprey, FL 34229
• 

  

  /49

  $897,000

  • 3 Beds
  • 2 Baths
  • 2,483 Sq Ft

  678 Crane Prairie Way, Osprey, FL 34229

  It’s always about the view and the new tile roof in June 2025 plus the Tesla whole-house solar system comprising 26 roof panels harnessing 8.45-kilowatt capacity of energy. This incredible benefit includes two Power Walls and a wall-mounted charging station supporting most brands of electric vehicles. The solar system reduces house energy costs to $27 a month and zero for your electric car. When

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  678 Crane Prairie Way, Osprey, FL 34229
• 

  /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
• 

  

  /37

  Est $408,494 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  117 Navigation Cir Unit 101, Osprey, FL 34229

  117 Navigation Cir Unit 101, Osprey, FL 34229
• 

  

  /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
• 

  /2

  $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
• 

  

  /57

  Est $701,199 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229
• 

  

  /99

  $6,750,000

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

  622 Bayshore Dr, Osprey, FL 34229

  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 defined by serenity, style and seamless connection to the water. Designed

  Terri Derr MICHAEL SAUNDERS & COMPANY

  622 Bayshore Dr, Osprey, FL 34229
• 

  /2

  $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
• 

  

  /37

  Est $602,146 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft

  514 Oak Bay Dr, Osprey, FL 34229

  514 Oak Bay Dr, Osprey, FL 34229
• 

  

  /43

  $685,000

  • 1,887 Sq Ft

  6 Bay Acres Ave, Osprey, FL 34229

  Exceptional Investment Opportunity – Profitable Remodeled Duplex in Prime Osprey Location! Updated in 2021 with a new roof, modern kitchens, contemporary appliances, stylish flooring, and upgraded electrical systems. This income-producing gem is currently generating $112,000 in gross annual short-term rental income, making it an unbeatable addition to your investment portfolio.Nestled on

  Bogdan Osipov OSIPOV GROUP REAL ESTATE

  6 Bay Acres Ave, Osprey, FL 34229
• 

  /2

  $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
• 

  

  /16

  Est $340,213 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 967 Sq Ft

  340 Pennsylvania Ave, Osprey, FL 34229

  340 Pennsylvania Ave, Osprey, FL 34229
• 

  

  /24

  $670,000

  • Land
  • 0.34 Acre
  • $1,970,588 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
• 

  /2

  $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
• 

  

  /63

  Est $1,169,759 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,048 Sq Ft

  113 Harbor House Dr, Osprey, FL 34229

  113 Harbor House Dr, Osprey, FL 34229
• 

  

  /41

  $164,900

  • 2 Beds
  • 2 Baths
  • 863 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
• 

  /2

  $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
• 

  

  /31

  Est $342,833 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 874 Sq Ft

  21 Shumard St, Osprey, FL 34229

  21 Shumard St, Osprey, FL 34229
• 

  

  /35

  $310,000 Open Sun 12PM - 2PM

  • 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

Showing Results 161 - 200, Page 5 of 18