21

Open Houses in 34229

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  • /78

    $850,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,869 Sq Ft

    1486 Landview Ln, Osprey, FL 34229

    Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout,

    Agent Photo

    Barbara Teyssier

    EXP REALTY LLC

    (941) 208-4807

    1486 Landview Ln, Osprey, FL 34229
  • /56

    $699,000 Open Sun 1PM - 3PM

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

    6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229

    BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of

    Agent Photo

    Scott Swonger

    HOMESMART

    (941) 304-4466

    6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229
  • /69

    $1,995,000 Open Sun 1PM - 3PM

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

    312 Yacht Harbor Dr, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s

    Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

    312 Yacht Harbor Dr, Osprey, FL 34229
  • /53

    $647,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,320 Sq Ft

    522 Luminary Blvd, Osprey, FL 34229

    This exquisite three-bedroom, three-bath-plus-den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    522 Luminary Blvd, Osprey, FL 34229
  • /48

    $895,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 2,283 Sq Ft

    172 Sea Anchor Dr, Osprey, FL 34229

    Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring,

    Sharon Lewis GOLF & BAY PROPERTIES LLC

    172 Sea Anchor Dr, Osprey, FL 34229
  • /74

    $1,749,990 Open Sat 12PM - 3PM

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

    140 Sugar Mill Dr, Osprey, FL 34229

    FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for

    Monica Verinder COLDWELL BANKER REALTY

    140 Sugar Mill Dr, Osprey, FL 34229
  • /61

    $719,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,306 Sq Ft

    665 Crane Prairie Way, Osprey, FL 34229

    Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    665 Crane Prairie Way, Osprey, FL 34229
  • /65

    $650,000 Open Sun 1AM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft

    250 Hidden Bay Dr Unit A302, Osprey, FL 34229

    ANOTHER PRICE IMPROVEMENT!!!!WHAT A VIEW and the pictures don't do it justice!! SELLER IS OFFERING to prepay three (3) months of HOA dues on behalf of the buyer at closing. FULLY FURNISHED/TURNKEY UNIT! (optional of course) Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful

    Merryl Koven COLDWELL BANKER REALTY

    250 Hidden Bay Dr Unit A302, Osprey, FL 34229
  • /23

    $525,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,947 Sq Ft

    437 S 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 about.

    Dawn Barnett EXIT KING REALTY

    437 S Shore Dr, Osprey, FL 34229
  • /100

    $1,695,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,425 Sq Ft

    228 Saint James Park, Osprey, FL 34229

    Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors

    Steve Abbe COLDWELL BANKER REALTY

    228 Saint James Park, Osprey, FL 34229
  • /69

    $897,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft

    664 Crane Prairie Way, Osprey, FL 34229

    It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    664 Crane Prairie Way, Osprey, FL 34229
  • /95

    $1,380,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    365 S Shore Dr, Osprey, FL 34229

    Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined

    Lisa Asaro EXIT KING REALTY

    365 S Shore Dr, Osprey, FL 34229
  • /36

    $569,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft

    1337 Copperwood Dr, Osprey, FL 34229

    This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1337 Copperwood Dr, Osprey, FL 34229
  • /37

    $1,499,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 2,798 Sq Ft

    1471 Shoal Way, Osprey, FL 34229

    One or more photo(s) has been virtually staged. This exceptional residence truly checks every box.Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the

    Lauren Doyle DALTON WADE INC

    1471 Shoal Way, Osprey, FL 34229
  • /51

    $449,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,284 Sq Ft

    107 Sorrento Dr, Osprey, FL 34229

    This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from

    Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

    107 Sorrento Dr, Osprey, FL 34229
  • /78

    $690,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,134 Sq Ft

    102 Windward Dr, Osprey, FL 34229

    NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers

    David Cyr WILLIAM RAVEIS FLORIDA LLC

    102 Windward Dr, Osprey, FL 34229
  • /41

    $179,900 Open Sun 2PM - 4PM

    • 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 add more

    John Alexander FINE PROPERTIES

    238 Palm Air Dr, Osprey, FL 34229
  • /41

    $719,000 Open Sun 3PM - 5PM

    • 2 Beds
    • 2 Baths
    • 1,932 Sq Ft

    242 Hidden Bay Dr Unit 602, Osprey, FL 34229

    Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features

    Cathy Rustin FIRST LIGHT REAL ESTATE

    242 Hidden Bay Dr Unit 602, Osprey, FL 34229
  • /99

    $1,095,000 Open Sat 2PM - 4PM

    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft

    403 Longbow Trail, Osprey, FL 34229

    Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort,

    Edward Bieker DALTON WADE INC

    403 Longbow Trail, Osprey, FL 34229
  • /47

    $264,900 Open Sun 1PM - 3PM

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

    232 Woodland Dr, Osprey, FL 34229

    This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within

    Pat Williams PAT WILLIAMS REALTY, LLC

    232 Woodland Dr, Osprey, FL 34229
  • /68

    $329,900 Open Sun 1PM - 3:30PM

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

    4304 Expedition Way Unit 105, Osprey, FL 34229

    Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances.Enjoy peaceful

    Tim Weller EXIT KING REALTY

    4304 Expedition Way Unit 105, Osprey, FL 34229
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