Osprey, FL Homes

• 

  

  /2

  $665,000 Sold May 23, 2025

  • 1,922 Sq Ft
  • $346/SF
  • 125 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1964

  123 Tina Island Dr, Osprey, FL 34229

  Spectacular lot and setting for home priced under county tax appraisal. This is your opportunity to own a waterfront property in the Sorrento Shores neighborhood in Osprey. This 3 bedroom, 3 bath pool home is ready for its new owners to renovate the property with cosmetic updates to create your new dream space. This property is a great investment for you to enjoy your future activities and

  Glenn Davis COLDWELL BANKER SARASOTA CENT.

  123 Tina Island Dr, Osprey, FL 34229
• 

  

  

  /41

  Est $563,621 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
• 

  

  

  /87

  $2,500,000

  • 3 Beds
  • 3.5 Baths
  • 2,473 Sq Ft

  140 N Casey Key Rd, Osprey, FL 34229

  Step into a world where the horizon meets the sea and every sunset paints a masterpiece. This exceptional cedar-sided residence on exclusive Casey Key offers the perfect blend of contemporary elegance and natural beauty along an eight-mile stretch of pristine shoreline. The home features three spacious bedrooms, each with a private ensuite, plus a beautifully appointed half bath on the lower

  Rhonda Carder EXP REALTY LLC

  140 N Casey Key Rd, Osprey, FL 34229
• 

  

  /2

  $1,020,000 Sold May 22, 2025

  • 2,909 Sq Ft
  • $351/SF
  • 14 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  284 Lookout Point Dr, Osprey, FL 34229

  Welcome to the much sought after Southbay Yacht and Racquet Club!!! You can be on vacation all year long with the private marina that has 172 boat slips that can accommodate yachts up to 55 feet. This one of a kind private marina will also accommodate personal water crafts and kayaks too!!. Our boat slip rentals are based on availability with a very attractive quarterly fee as compared to other

  Carol Thompson ROYAL PALM REALTY

  284 Lookout Point Dr, Osprey, FL 34229
• 

  

  

  /79

  Est $1,332,980 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
• 

  

  /48

  $225,000

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

  244 Woodland Dr Unit 244, Osprey, FL 34229

  Tranquil Coastal Living in Pine Run244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  244 Woodland Dr Unit 244, Osprey, FL 34229
• 

  /2

  $835,000 Sold May 21, 2025

  • 2,214 Sq Ft
  • $377/SF
  • 42 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2006

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVATOR and into this PENTHOUSE UNIT you’ll be amazed by the SPECTACULAR VIEWS overlooking Little Sarasota Bay and the Intracoastal Waterway (ICW). This 3 bed/3.5bath, TURNKEY FURNISHED unit, has been freshly painted inside and features newer flooring, crown

  Adam Waxler UKEEPCOMMISSION REAL ESTATE

  14021 Bellagio Way Unit 410, Osprey, FL 34229
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  /45

  Est $2,617,871 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
• 

  

  /3

  $89,000

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Hurricane-protected dry storage with top-tier amenities! This slip 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 swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
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  /66

  $155,000 Sold May 15, 2025

  • 736 Sq Ft
  • $211/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1973

  767 Pine Run Dr, Osprey, FL 34229

  Welcome to 767 Pine Run Drive in sunny Osprey, FL—located between Sarasota and Venice so you can easily enjoy the beaches, shopping, arts and entertainment of both towns. This 736 square-foot home is all about easy living, featuring an open floor plan and soaring ceilings that let in tons of natural light. You’ll love the sun-drenched living and dining areas, with huge sliding doors that open to

  Priscilla Adams COMPASS FLORIDA LLC

  767 Pine Run Dr, Osprey, FL 34229
• 

  

  /50

  Est $362,865 Not Listed For Sale

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

  1821 Highland Rd, Osprey, FL 34229

  1821 Highland Rd, Osprey, FL 34229
• 

  

  /39

  $1,100,000

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

  385 N Point Rd Unit 903, Osprey, FL 34229

  One or more photo(s) has been virtually staged. From the moment the private elevator doors open, the panorama of the view has you at ‘hello,” with a northwest-facing expanse over the preserve, the lagoon below, Sarasota Bay and the Gulf beyond. This orientation brings cooler interiors, dramatic natural light and unforgettable sunsets. Rare 10’ ceilings amplify the spaciousness and invite the

  Ryan Ackerman COLDWELL BANKER REALTY

  385 N Point Rd Unit 903, Osprey, FL 34229
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  /69

  $265,000 Sold May 15, 2025

  • 1,379 Sq Ft
  • $192/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  360 Pine Run Dr Unit 360, Osprey, FL 34229

  Welcome to 360 Pine Run Drive, a stunning residence nestled in the heart of Osprey, FL. This beautifully updated 2-bedroom, 2-bathroom condo spans 1,379 square feet and is the largest of its kind in the community. Designed by the renowned architect Frank Folsom Smith, this home is a masterpiece of the Sarasota School of Architecture, offering a seamless blend of style and functionality.As you

  Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
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  /86

  Est $1,602,710 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
• 

  

  /100

  $2,350,000

  • 3 Beds
  • 2.5 Baths
  • 3,738 Sq Ft

  393 N Point Rd Unit 1002, Osprey, FL 34229

  Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who values quality, elegance, and an unparalleled location. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with

  Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 1002, Osprey, FL 34229
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  /2

  $520,000 Sold May 14, 2025

  • 1,700 Sq Ft
  • $306/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  544 Meadow Sweet Cir, Osprey, FL 34229

  Welcome to this charming 3-bedroom, 2-bathroom, maintenance-free single-family home in Osprey, Florida!Located in the unique Cottages of Rivendell Community, this neighborhood offers a warm and welcomingenvironment where neighbors become friends from day one. Under the mature trees, you can walk in the shadeeven the warmest day of the year.As you step through the beautiful double

  Zita Bowers MICHAEL SAUNDERS & COMPANY

  544 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  Est $880,001 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,968 Sq Ft

  1321 Southbay Dr, Osprey, FL 34229

  1321 Southbay Dr, Osprey, FL 34229
• 

  

  /51

  $479,000

  • 2 Beds
  • 2 Baths
  • 2,148 Sq Ft

  32 Bay Ave, Osprey, FL 34229

  Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating and waterfront lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater,

  Enya Overholser NEXTHOME BEACH TO BAY

  32 Bay Ave, Osprey, FL 34229
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  /55

  $480,000 Sold May 14, 2025

  • 1,808 Sq Ft
  • $265/SF
  • 57 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  564 Meadow Sweet Cir, Osprey, FL 34229

  Discover serenity and peace of mind in this idyllic property in the sought after Cottages of Rivendell. Close to breathtaking Casey Key, Siesta Key Beach, Nokomis Beach and the crystal blue waters of the Gulf of Mexico. This home offers an excellent location with convenient access to all modern amenities. Enjoy the luxury of being short distance to the nationally acclaimed Pine View School. The

  Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  564 Meadow Sweet Cir, Osprey, FL 34229
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  /69

  Est $628,766 Not Listed For Sale

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

  521 Bayshore Dr, Osprey, FL 34229

  521 Bayshore Dr, Osprey, FL 34229
• 

  

  /48

  $189,900

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  238 Woodland Dr, Osprey, FL 34229

  Live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding patio door to the

  Kellie MacDonell COLDWELL BANKER REALTY

  238 Woodland Dr, Osprey, FL 34229
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  /2

  $710,000 Sold May 09, 2025

  • 2,533 Sq Ft
  • $280/SF
  • 117 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2002

  710 Shadow Bay Way, Osprey, FL 34229

  Florida’s perfect floor plan! Built in 2002, this home features soaring ceilings, engineered hardwood maple floors that are softer and warmer underfoot than tile, and a thoughtfully designed layout for both living and entertaining. The great room, complete with a cozy wood-burning fireplace, flows seamlessly into a formal dining room, a spacious eat-in kitchen, and a versatile office. The serene

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  710 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $1,709,906 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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  /77

  $7,100,000

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

  121 N Casey Key Rd, Osprey, FL 34229

  Newly Remodeled Gulf-Front Mediterranean Villa on Casey KeyFramed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence

  Lisa Napolitano DOUGLAS ELLIMAN

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

  $780,000 Sold May 08, 2025

  • 2,154 Sq Ft
  • $362/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  779 Fordingbridge Way, Osprey, FL 34229

  Discover the park like unhurried living of Rivendell, known for its tree lined streets, friendly neighbors. Residents enjoy 380 acres with 200 acres as preserves, lakes, open spaces, and trails. Fully remodeled one owner home meticulously maintained, new tile roof Jan 2025, impact glass windows all around, fully remodeled 2154 sqft in a great room design. All on a 0.46-acre private preserve view

  Leonard Giarrano RE/MAX ALLIANCE GROUP

  779 Fordingbridge Way, Osprey, FL 34229
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  /3

  Est $235,241 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 858 Sq Ft

  110 Oak St, Osprey, FL 34229

  110 Oak St, Osprey, FL 34229
• 

  

  /68

  $2,299,000

  • 4 Beds
  • 4 Baths
  • 2,572 Sq Ft

  312 Yacht Harbor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  312 Yacht Harbor Dr, Osprey, FL 34229
• 

  /2

  $340,000 Sold May 08, 2025

  • 1,568 Sq Ft
  • $217/SF
  • 166 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  First-floor end-unit with hurricane-rated windows and lots of natural light, in the gated community of Hidden Bay that sits on the shores of Little Sarasota Bay. This unit includes a one-car garage, a screened lanai, two spacious bedrooms, two full baths, and a separate office and den. You'll find high ceilings, new luxury vinyl flooring throughout most of the unit, new air-conditioning system, a

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229
• 

  

  /11

  Est $830,588 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
• 

  

  /62

  $875,000

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229

  END UNIT with RARE THREE CAR GARAGE, IMPACT WINDOWS AND SLIDERS, and sweeping panoramic views. This beautifully appointed Baypointe Vista condo in Osprey blends comfort, style, and convenience, all set against the backdrop of the Intracoastal Waterway and Little Sarasota Bay.Natural light pours through wide water view windows, while plantation shutters throughout add timeless coastal

  Bart Tracy LASBURY-TRACY REALTY INC.

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229
• 

  /2

  $1,600,000 Sold May 01, 2025

  • 5,987 Sq Ft
  • $267/SF
  • 1 Day On Market

  • 5 Beds
  • 7.5 Baths
  • Built 1991

  916 MacEwen Dr, Osprey, FL 34229

  Situated on a double lot behind the secure gates of The Oaks, this two story 5 bedroom home, with 7.5 bathrooms, boasts fantastic potential and excellent bones. The only thing it needs is for you to put your personal touch on it and make it your own. As you pull up to this home, using the front circular driveway, or the back driveway with access to the 4 CAR GARAGE, you will immediately be taken

  Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
• 

  

  /70

  Est $1,575,796 Not Listed For Sale

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

  337 Passage Way, Osprey, FL 34229

  337 Passage Way, Osprey, FL 34229
• 

  

  /60

  $925,000

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft

  38 W Bay St, Osprey, FL 34229

  Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen with solid wood cabinets, stainless

  Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
• 

  /2

  $875,000 Sold May 01, 2025

  • 2,329 Sq Ft
  • $376/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  851 E Bay St, Osprey, FL 34229

  **BEAUTIFULLY RENOVATED, PRIVATE OASIS AWAITS on this OVERSIZED 1.37 ACRE ESTATE with NO HOA** This GREEN BUILT (insulated concrete form constructed), Move-In Ready Residence offers 3-BEDS and 2-FULL BATHS, while Recent UPDATES include beautiful Flooring, Impressive Primary Bedroom Suite with walk-in closet and Stunning Primary Bath featuring dual vanities, custom-tiled shower and soaking tub, a

  Mark Lyda GENEROUS PROPERTY

  851 E Bay St, Osprey, FL 34229
• 

  

  /24

  Est $836,905 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
• 

  

  /8

  $750,000

  • Land
  • 0.47 Acre
  • $1,595,745 per Acre

  147 Osprey Point Dr, Osprey, FL 34229

  Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida‘s most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand and luxurious homes in the entire gulf coast region. The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of

  Mick Jordan BRIGHT REALTY

  147 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  $395,000 Sold Apr 30, 2025

  • 1,767 Sq Ft
  • $224/SF
  • 81 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  418 Sarabay Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! Welcome to 418 Sarabay Rd, a lovely old-Florida home "West of Trail" in the charming community of Osprey, exuding a small-town feel, but just minutes away from all the conveniences and excitement of Sarasota and Venice! You and your guests will be drawn to spend lots of time in this fully fenced private oasis with its large

  Tracey Fiedler DALTON WADE INC

  418 Sarabay Rd, Osprey, FL 34229
• 

  

  /65

  Est $961,093 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft

  599 Pine Ranch East Rd, Osprey, FL 34229

  599 Pine Ranch East Rd, Osprey, FL 34229
• 

  

  /46

  $545,000

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include:

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
• 

  /2

  $318,000 Sold Apr 30, 2025

  • 1,411 Sq Ft
  • $225/SF
  • 125 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  115 Villa Dr Unit 115, Osprey, FL 34229

  Welcome to your future waterfront retreat in the heart of Osprey, where coastal living meets convenience. This beautifully appointed villa offers 1,411 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms in a flowing, open-concept layout.The primary bedroom suite provides a peaceful sanctuary with an ensuite bathroom and generous closet space.

  EJ Stukenborg KELLER WILLIAMS ON THE WATER S

  115 Villa Dr Unit 115, Osprey, FL 34229

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