17

Osprey, FL Open Houses

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  • /60

    $1,150,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    353 S Shore Dr, Osprey, FL 34229

    Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway just a few homes down the canal. A true boater’s dream, your private dock provides quick and easy access to some of the area’s most beloved waterfront

    Agent Photo

    Phyllis Coviello

    COLDWELL BANKER SARASOTA CENT.

    (941) 420-6389

    353 S Shore Dr, Osprey, FL 34229
  • /74

    $1,399,000 Open Sun 12PM - 3PM

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

    140 Sugar Mill Dr, Osprey, FL 34229

    SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! 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

    Monica Verinder COLDWELL BANKER REALTY

    140 Sugar Mill Dr, Osprey, FL 34229
  • /78

    $1,750,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 3.5 Baths
    • 3,565 Sq Ft

    402 E MacEwen Dr, Osprey, FL 34229

    Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that

    Steven Kepecz, PA COLDWELL BANKER REALTY

    402 E MacEwen Dr, Osprey, FL 34229
  • /95

    $1,349,000 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
  • /82

    $1,150,000 Open Sun 1PM - 4PM

    • 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 a

    Deborah Frederick ASHTON LAKES REALTY INC

    296 Pine Ranch Trail, Osprey, FL 34229
  • /53

    $639,000 Open Sun 1PM - 3PM

    • 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
  • /71

    $735,000 Open Sun 1PM - 4PM

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229

    Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining

    Suki Scollo COLDWELL BANKER REALTY

    5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229
  • /13

    $548,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,861 Sq Ft

    4428 Conchfish Ln, Osprey, FL 34229

    Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

    Mariana Georgieva HORIZON REALTY INTERNATIONAL

    4428 Conchfish Ln, Osprey, FL 34229
  • /39

    $550,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    1361 New Forest Ln, Osprey, FL 34229

    Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile

    Linh Pham NEXTHOME EXCELLENCE

    1361 New Forest Ln, Osprey, FL 34229
  • /63

    $887,000 Open Sun 1PM - 3PM

    • 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
  • /61

    $1,950,000 Open Sun 12PM - 3PM

    • 5 Beds
    • 5.5 Baths
    • 4,885 Sq Ft

    97 Sugar Mill Dr, Osprey, FL 34229

    Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed

    Maria 'Indy' Domenech PALM PARADISE REALTY GROUP

    97 Sugar Mill Dr, Osprey, FL 34229
  • /36

    $550,000 Open Sun 1PM - 3PM

    • 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
  • /78

    $650,000 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
  • /96

    $3,150,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 3.5 Baths
    • 2,665 Sq Ft

    14401 Masthead Dr, Osprey, FL 34229

    Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you

    Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

    14401 Masthead Dr, Osprey, FL 34229
  • /70

    $694,000 Open Sun 1PM - 4PM

    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    260 Hidden Bay Dr Unit B-304, Osprey, FL 34229

    The Boca Residence: Spacious Living & Resort StyleDiscover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal

    Janice Martin ENGEL & VOELKERS VENICE DOWNTOWN

    260 Hidden Bay Dr Unit B-304, Osprey, FL 34229
  • /77

    $329,500 Open Sun 11AM - 2PM

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

    4304 Expedition Way Unit 105, Osprey, FL 34229

    One or more photo(s) has been virtually staged. 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

    Tim Weller EXIT KING REALTY

    4304 Expedition Way Unit 105, Osprey, FL 34229
  • /50

    $656,500 Open Sun 1PM - 3PM

    • 4 Beds
    • 4 Baths
    • 2,573 Sq Ft

    4042 Westbourne Cir, Sarasota, FL 34238

    Pride of ownership is evident throughout this meticulously maintained home, offering an impressive array of thoughtful upgrades and modern features. A new roof and gutters were installed in 2025, and the home is equipped with dual-zone HVAC systems updated in 2021 and 2024 for optimal comfort and efficiency. Step outside to your private retreat, featuring a screened-in pool with serene lake views

    William Kelly THE REAL ESTATE STORE

    4042 Westbourne Cir, Sarasota, FL 34238

Home Trends in Osprey, FL

Housing Trends

Median Sale Price
$669,000
Median Single Family Sale Price
$882,500
Median Townhouse Sale Price
$467,000
Median 2 Bedroom Sale Price
$307,000
Median 1 Bedroom Sale Price
$217,500
Average Price Per Sq Ft
$384
Number of Homes for Sale
135
Last 12 months Home Sales
185
Months of Supply
8.80
Median List Price
$750,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-13%
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