Osprey, FL Homes

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  /68

  Est $880,901 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,982 Sq Ft

  1081 Scherer Way, Osprey, FL 34229

  1081 Scherer Way, Osprey, FL 34229
• 

  

  

  /11

  $705,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  110 Pine Ave, Osprey, FL 34229

  Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

  Marisa Marino BRIGHT REALTY

  110 Pine Ave, Osprey, FL 34229
• 

  

  /2

  $500,000 Sold Mar 21, 2025

  • 1,867 Sq Ft
  • $268/SF
  • 250 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1996

  629 Oak Bay Dr, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** Indulge in the ultimate Florida lifestyle with this captivating 4-bedroom, 2-bathroom pool home nestled within the community of Bay Oaks Estates. Lush greenery and a charming front porch that exudes curb appeal sets the stage for what lies within. As you step through the front door, prepare

  Toni Zarghami KW COASTAL LIVING III

  629 Oak Bay Dr, Osprey, FL 34229
• 

  

  

  /43

  Est $486,267 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  1130 Beachcomber Ct, Osprey, FL 34229

  1130 Beachcomber Ct, Osprey, FL 34229
• 

  

  

  /20

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,389 Sq Ft

  208 Villa Dr Unit 208, Osprey, FL 34229

  Don’t miss this opportunity to own a fully updated, move-in-ready Condo in an incredible location! With its proximity to the beach and low HOA fees this property is perfect for those first time Homebuyers or Snow Birds seeking a comfortable coastal lifestyle within a budget! Welcome to this beautifully updated spacious single story condo, with a split bedroom floor plan, boasting 2 bedrooms with

  Jason Saphire WWW.HOMEZU.COM

  208 Villa Dr Unit 208, Osprey, FL 34229
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  /32

  $335,000 Sold Mar 12, 2025

  • 1,700 Sq Ft
  • $197/SF
  • 26 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  738 Harms Dr, Osprey, FL 34229

  ***Osprey “West of the Trail” – Incredible Opportunity for a Cash Buyer*** Fully fenced, HALF AN ACRE, featuring a 2-bed, 2-bath home plus a 1-bed, 1-bath in-law/ADU suite with a pool. This 0.5-acre property is located in an X flood zone, with no flooding or damage from recent hurricanes. There are endless possibilities—update the existing home or BUILD YOUR DREAM HOME on this fantastic lot, just

  Warren McGregor MCGREGOR INTERNATIONAL REAL ESTATE CO

  738 Harms Dr, Osprey, FL 34229
• 

  

  /37

  Est $866,088 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  192 Park Trace Blvd, Osprey, FL 34229

  192 Park Trace Blvd, Osprey, FL 34229
• 

  

  /88

  $2,900,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Louis XVI fireplace anchors the sunken living room, while French doors and expansive windows invite

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /72

  $615,000 Sold Mar 10, 2025

  • 2,340 Sq Ft
  • $263/SF
  • 194 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  593 Crane Prairie Way, Osprey, FL 34229

  Welcome to Willowbend a custom built community by Lee Wetherington. This maintenance free Asley ll model home is nearly 2400 sq. ft. under air with 4 bedrooms & 3 baths. Expansive 33x25 ft. lanai includes 2 covered areas & expansive water views. High tray ceilings in master bedroom & family room with crown molding & 8ft. doors. Gourmet kitchen features Corian counters, stainless steel appliances

  Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

  593 Crane Prairie Way, Osprey, FL 34229
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  /2

  Est $2,679,964 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,937 Sq Ft

  388 Bunker Hill, Osprey, FL 34229

  388 Bunker Hill, Osprey, FL 34229
• 

  

  /64

  $4,750,000

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft

  1049 N Casey Key Rd, Osprey, FL 34229

  Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida

  Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

  1049 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $772,000 Sold Mar 04, 2025

  • 2,306 Sq Ft
  • $335/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  663 Crane Prairie Way, Osprey, FL 34229

  This exquisite four-bedroom, three-bath home by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. The Ashley floor plan is thoughtfully oriented to the west, allowing for abundant natural light and stunning sunset views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom double-door

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  663 Crane Prairie Way, Osprey, FL 34229
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  /29

  Est $2,262,266 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,747 Sq Ft

  162 Puesta Del Sol, Osprey, FL 34229

  162 Puesta Del Sol, Osprey, FL 34229
• 

  

  /60

  $11,750,000

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

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /2

  $925,000 Sold Mar 03, 2025

  • 2,928 Sq Ft
  • $316/SF
  • 118 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  1200 Mallard Marsh Dr, Osprey, FL 34229

  Location, Location, Location!!!!!! This 4 Bedroom, 3 bathroom, and den home also has a 3 Car garage! This home has some of the very best views of a large lake and it backs up to Oscar Shear State Park. Across the street from the front is beautiful butterfly park for total refuge and privacy. The roof is a brand-new slate roof with a 25-year warranty! The entire house has hurricane impact glass

  Sharon Osborne, PA RESULTS REALTY GROUP LLC

  1200 Mallard Marsh Dr, Osprey, FL 34229
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  /84

  Est $1,207,145 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft

  513 S Creek Dr, Osprey, FL 34229

  513 S Creek Dr, Osprey, FL 34229
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  /51

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft

  14021 Bellagio Way Unit 309, Osprey, FL 34229

  A boaters paradise. Discover the epitome of coastal living in this stunning 3-bedroom, 2.5-bathroom condo located in the highly desired, Bellagio Harbor Village. Nestled in between Sarasota Big Pass and the Venice Jetty, just minutes from Midnight pass and the gulf, this property offers prompt access to Sarasota County’s pristine beaches, fine dining, and boutique shopping.With a generous

  Tristin Hopler EXP REALTY LLC

  14021 Bellagio Way Unit 309, Osprey, FL 34229
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  /2

  $425,000 Sold Feb 25, 2025

  • 1,648 Sq Ft
  • $258/SF
  • 140 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  2068 Preymore St, Osprey, FL 34229

  Your opportunity awaits to live in this beautiful 3-bedroom, 2 bath home situated on a quiet street with no HOA fees and no flood zone! Lovely landscaping and great curb appeal. This home lives larger than the square footage would indicate offering a large great room, ample dining room and spacious primary suite. Cathedral ceilings, pocket sliding doors and open floor plan lend itself to easy

  Karen Geiger COLDWELL BANKER SARASOTA CENT.

  2068 Preymore St, Osprey, FL 34229
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  /60

  Est $1,105,916 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,738 Sq Ft

  228 Lookout Point Dr, Osprey, FL 34229

  228 Lookout Point Dr, Osprey, FL 34229
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  /92

  $1,300,000

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

  393 N Point Rd Unit 604, Osprey, FL 34229

  Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
• 

  /2

  $656,000 Sold Feb 21, 2025

  • 2,125 Sq Ft
  • $309/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  1109 Scherer Way, Osprey, FL 34229

  This fabulous residence, featuring a new tile roof installed in November 2024 and hurricane-impact windows and shutters for the patio doors, is set against the backdrop of a sparkling lake, offering stunning scenic views and a vibrant array of local wildlife. In the Woodlands of Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes, this home provides

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1109 Scherer Way, Osprey, FL 34229
• 

  /2

  Est $215,166 Not Listed For Sale

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

  120 Woodland Place Unit 120, Osprey, FL 34229

  120 Woodland Place Unit 120, Osprey, FL 34229
• 

  

  /53

  $395,000

  • Land
  • 0.24 Acre
  • $1,645,833 per Acre

  51 N Tamiami Trail, Osprey, FL 34229

  Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and

  Betsy De Manio COLDWELL BANKER REALTY

  51 N Tamiami Trail, Osprey, FL 34229
• 

  /2

  $740,000 Sold Feb 21, 2025

  • 2,707 Sq Ft
  • $273/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  1076 Mallard Marsh Dr, Osprey, FL 34229

  Welcome to the POOL home at the sought after RIVENDELL. This spacious home is located in the acclaimed PINEVIEW SCHOOL DISTRICT.OVERSIZED LOT BACKING TO A PRESERVE. Three bedroom plus den and two full bathrooms plus half bath. The mature landscaped lawn welcomes you to enter the double glassed doors with transom windows into the spacious open floor-plan home. You will find the vaulted

  Reeny Kaney RE/MAX ALLIANCE GROUP

  1076 Mallard Marsh Dr, Osprey, FL 34229
• 

  /2

  Est $569,843 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,204 Sq Ft

  685 Clear Creek Dr, Osprey, FL 34229

  685 Clear Creek Dr, Osprey, FL 34229
• 

  

  /62

  $660,000

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft

  385 N Point Rd Unit 402, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 402, Osprey, FL 34229
• 

  /2

  $615,000 Sold Feb 21, 2025

  • 1,932 Sq Ft
  • $318/SF
  • 86 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  242 Hidden Bay Dr Unit 403, Osprey, FL 34229

  Enjoy breathtaking 180º views of the Intracoastal Waterway and Little Sarasota Bay from this beautifully updated fourth-floor unit in Baypointe Vista, Osprey. Priced to sell, this inviting residence features a spacious foyer with engineered hardwood floors, 8-foot doors, open floorplan, split bedrooms and a soothing neutral color palette. The home showcases unobstructed views of Casey Key and

  Tina Renta KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  242 Hidden Bay Dr Unit 403, Osprey, FL 34229
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  /45

  Est $757,903 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  866 Placid Lake Dr, Osprey, FL 34229

  866 Placid Lake Dr, Osprey, FL 34229
• 

  

  /59

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,729 Sq Ft

  304 Pine Run Dr, Osprey, FL 34229

  LIMITED SUPPLY LEFT IN PINE RUN - MOTIVATED SELLER - Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr., a beautifully architecturally designed property nestled in the sought-after Pine Run community in Osprey, FL. Surrounded by lush tropical landscaping and just minutes from the Gulf Coast’s pristine beaches, this residence

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  304 Pine Run Dr, Osprey, FL 34229
• 

  /2

  $400,000 Sold Feb 18, 2025

  • 2,768 Sq Ft
  • $145/SF
  • 41 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1956

  108 Park Dr, Osprey, FL 34229

  Welcome to your dream home! This oversized pool home is perfectly situated just minutes from the intercoastal, offering quick and easy access to launch your boat or jet ski. With four bedrooms, three bathrooms, and an abundance of space, this property is a rare find. The first floor boasts durable terrazzo flooring throughout, with even more Terrazzos hidden beneath the tiled areas.

  Michele Monteiro COLDWELL BANKER REALTY

  108 Park Dr, Osprey, FL 34229
• 

  

  /55

  Est $988,755 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,360 Sq Ft

  792 Placid Lake Dr, Osprey, FL 34229

  792 Placid Lake Dr, Osprey, FL 34229
• 

  

  /44

  $910,000

  • 3 Beds
  • 2 Baths
  • 2,271 Sq Ft

  293 Turquoise Ln, Osprey, FL 34229

  **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

  Mark Lyda GENEROUS PROPERTY

  293 Turquoise Ln, Osprey, FL 34229
• 

  /2

  $35,000 Sold Feb 17, 2025

  • 234 Days On Market

  570 Blackburn Point Rd Unit C2, Osprey, FL 34229

  For sale 36’ dry rack boat storage at Osprey Harbor Club Marina Casey 2 slip Buy your boat a home, Real Property tax ID #0157032002 Super convenient Location Osprey Harbor Village at 570 Blackburn Point Road, Osprey, FL 34229 Overall cube size is 9’- 6” wide x 8’ high x 36’ long and will fit boat up to 8’- 6” wide x 6’ high x 35’- 6” long Single owner purchased new 2006 35’ Fountain Executioner

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit C2, Osprey, FL 34229
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  /45

  Est $701,046 Not Listed For Sale

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

  573 Crane Prairie Way, Osprey, FL 34229

  573 Crane Prairie Way, Osprey, FL 34229
• 

  

  /51

  $525,000

  • 3 Beds
  • 2 Baths
  • 2,559 Sq Ft

  566 Oak Bay Dr, Osprey, FL 34229

  **Seller is motivated**Welcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a classic Florida home featuring a pool with mosaic inspired ocean theme. And with no one behind you and no houses in front offers plenty of privacy. Oh, I almost forgot this home offers a wood burning fire place for those couple of cold nights a year, lol. New roof September 2022 newer water heater. This

  Greg Walters SARABAY REAL ESTATE INC

  566 Oak Bay Dr, Osprey, FL 34229
• 

  /2

  $999,500 Sold Feb 14, 2025

  • 2,627 Sq Ft
  • $380/SF

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  146 Yacht Harbor Dr, Osprey, FL 34229

  This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. Updated with a spacious, open layout, this pool home boasts many features that set it apart from others. The great room is expansive with an attractive electric fireplace and ultra-high ceilings. Adjacent to it is a custom kitchen with quartz

  Susanne Losso COLDWELL BANKER REALTY

  146 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /40

  Est $747,094 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft

  669 Crane Prairie Way, Osprey, FL 34229

  669 Crane Prairie Way, Osprey, FL 34229
• 

  

  /68

  $324,900

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229

  Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little Sarasota Bay, this gated community offers waterfront play and relaxation. Spend your perfect day at the amenity rich community clubhouse/pool or kayaking on Intracoastal waters. This lovely two-bedroom, two-bath home is roomy and bright, offering a den/office along with a

  Kristen Redding MICHAEL SAUNDERS & COMPANY

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229
• 

  /2

  $1,799,000 Sold Feb 14, 2025

  • 1,857 Sq Ft
  • $969/SF
  • 13 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1975

  716 Sarabay Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Stunning Waterfront Property on Little Sarasota Bay! Discover a rare opportunity to own a magnificent estate lot on the Intracoastal Waterway in beautiful Osprey, Florida. This exceptional property features 100 feet of prime waterfrontage; Dock and boat lift grandfathered in, making it a boater’s dream!Nestled on a spacious 1.23-acre lot, this

  Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  716 Sarabay Rd, Osprey, FL 34229
• 

  

  /32

  Est $628,048 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft

  727 Shadow Bay Way, Osprey, FL 34229

  727 Shadow Bay Way, Osprey, FL 34229

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