22

Osprey, FL Homes for Sale with Acreage

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  • /50

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,799 Sq Ft

    14041 Bellagio Way Unit 214, Osprey, FL 34229

    Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village-3 Bedrooms | 2 Bathrooms | Direct Intracoastal FrontageRare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and

    Agent Photo

    Veronica Lee

    COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 214, Osprey, FL 34229
  • /100

    $1,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,354 Sq Ft

    296 Pine Ranch Trail, Osprey, FL 34229

    Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large

    Agent Photo

    Darren Dowling

    BEYOND REALTY LLC

    296 Pine Ranch Trail, Osprey, FL 34229
  • /44

    $235,000

    $65K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    51 MacEwen Dr Unit 5, Osprey, FL 34229

    Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental.Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly

    Sabine Spycher 342 REAL ESTATE

    51 MacEwen Dr Unit 5, Osprey, FL 34229
  • /4

    $115,000

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

    This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric.

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229
  • /4

    $36,000

    570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

    This slip will house a boat with the maximum dimensions of 35.5' length, 10' width and 6' height This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
  • /45

    $249,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    116 Woodland Place Unit 116, Osprey, FL 34229

    Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such

    Pat Williams PAT WILLIAMS REALTY, LLC

    116 Woodland Place Unit 116, Osprey, FL 34229
  • /36

    $2,850,000

    • Land
    • 4.18 Acres
    • $681,818 per Acre

    2301 S Tamiami Trail, Osprey, FL 34229

    This listing is for 4.2 +/- acres consisting of two parcels that are rectangular in shape, cleared and level. The parcels have 700 +/- linear feet on US 41 (Tamiami Trail). The daily traffic counts that pass by this property are 41,500 vehicles. The property is currently zoned OPI (Office, Professional and Institutional) and RSF 2 (Residential Single Family 3.5 units / acre). There are two full

    Michael Gallatin SARABAY REAL ESTATE INC

    2301 S Tamiami Trail, Osprey, FL 34229
  • /4

    $109,000

    570 Blackburn Point Rd Unit 13, Osprey, FL 34229

    The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit 13, Osprey, FL 34229
  • /36

    $299,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    4226 Frontier Ln Unit 103, Osprey, FL 34229

    Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage

    Kate Kwiecinski COLDWELL BANKER REALTY

    4226 Frontier Ln Unit 103, Osprey, FL 34229
  • /71

    $9,750,000

    • 5 Beds
    • 8 Baths
    • 8,050 Sq Ft

    1216 N Casey Key Rd, Osprey, FL 34229

    At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare,

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1216 N Casey Key Rd, Osprey, FL 34229
  • /39

    $719,000

    New Construction $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft

    280 Hidden Bay Dr Unit 302, Osprey, FL 34229

    Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    280 Hidden Bay Dr Unit 302, Osprey, FL 34229
  • /38

    $165,900

    $6K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 586 Sq Ft

    701 Pine Run Dr, Osprey, FL 34229

    Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a

    Pat Williams PAT WILLIAMS REALTY, LLC

    701 Pine Run Dr, Osprey, FL 34229
  • /4

    $99,500

    570 Blackburn Point Rd Unit 36, Osprey, FL 34229

    This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 9' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks,

    David Babel BRIGHT REALTY

    570 Blackburn Point Rd Unit 36, Osprey, FL 34229
  • /30

    $284,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft

    184 Explorer Dr, Osprey, FL 34229

    Luxury Corner Residence in Osprey | Top-Rated Pine View School District.Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities.This FULLY FURNISHED 2-bedroom, 2-bathroom

    Claudia Dybala DALTON WADE INC

    184 Explorer Dr, Osprey, FL 34229
  • /4

    $39,500

    $3K PRICE DROP

    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 9.5W x 6.5H. With valet boat service,

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
  • /62

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,778 Sq Ft

    385 N Point Rd Unit 304, Osprey, FL 34229

    **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

    Mark Lyda GENEROUS PROPERTY

    385 N Point Rd Unit 304, Osprey, FL 34229
  • /16

    $1,350,000

    $50K PRICE DROP
    • Land
    • 2.51 Acres
    • $537,849 per Acre

    2099 S Tamiami Trail, Osprey, FL 34229

    NEW PRICE! Location! Location! This 2.51 Acre Lot is available for sale directly on South Tamiami Trail in Osprey - where Sarasota is growing and expanding! This property is zoned OPI and would be a good fit for a dental, veterinary, medical center or business offices with potential residential above. Great exposure with consistently heavy traffic from Sarasota to Naples on S. Tamiami Trail just

    Susan Repp COLDWELL BANKER REALTY

    2099 S Tamiami Trail, Osprey, FL 34229
  • /91

    $459,900

    $215K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,594 Sq Ft

    401 N Point Rd Unit 301, Osprey, FL 34229

    Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and

    Steve Abbe COLDWELL BANKER REALTY

    401 N Point Rd Unit 301, Osprey, FL 34229
  • /48

    $599,000

    $86K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,055 Sq Ft

    409 N Point Rd Unit 502, Osprey, FL 34229

    **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

    Mark Lyda GENEROUS PROPERTY

    409 N Point Rd Unit 502, Osprey, FL 34229
  • /97

    $1,900,000

    • 5 Beds
    • 7.5 Baths
    • 5,986 Sq Ft

    916 MacEwen Dr, Osprey, FL 34229

    Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness.

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    916 MacEwen Dr, Osprey, FL 34229
  • /99

    $1,095,000

    $102K PRICE DROP
    • 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

    Edward Bieker DALTON WADE INC

    403 Longbow Trail, Osprey, FL 34229
  • /50

    $4,795,000

    • 5 Beds
    • 3.5 Baths
    • 4,914 Sq Ft

    4678 Silent Creek Way, Nokomis, FL 34275

    Tucked away at the end of a quiet road on a breathtakingly private one-acre homesite, this extraordinary luxury gated estate overlooks the serene waters of South Creek with the untouched natural beauty of Oscar Scherer State Park creating an incomparable backdrop. Completely reimagined with a sophisticated contemporary aesthetic, this custom-built residence blends timeless architecture with

    Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4678 Silent Creek Way, Nokomis, FL 34275

Home Price Trends

Median Sale Price
$652,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$200,000
Average Price Per Sq Ft
$358
Number of Homes for Sale
80
Last 12 months Home Sales
206
Months of Supply
4.70
Median List Price
$749,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-13%
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