Osprey, FL Homes

/87
$995,000
- 3 Beds
- 2 Baths
- 2,606 Sq Ft
105 Turquoise Ln, Osprey, FL 34229

Welcome to Emerald Woods, a desired cul-de-sac within The Oaks Preserve, and this private LeeWetherington custom home that will check all the boxes, and more. Situated on one of thelargest lots and surrounded by preserve for privacy, you’ll find essence and elegance as thecolor palette interplays with natural light, and the southern facing lanai and pool will be whereyou can enjoy

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

105 Turquoise Ln, Osprey, FL 34229
/2
$945,000 Sold Apr 15, 2025
- 2,677 Sq Ft
- $353/SF
- 4 Days On Market
- 3 Beds
- 3 Baths
- Built 1978
128 Sea Anchor Dr, Osprey, FL 34229

New to the market, your dream home awaits in the exclusive private marina community of Southbay Yacht and Racquet Club. For boating enthusiasts, this is the opportunity you’ve been waiting for! In the sought-after Southbay Yacht and Racquet Club, this stunning residence combines spacious design with the best of Florida living, just steps from your boat. Imagine waking up and stepping out onto

Lisa Napolitano DOUGLAS ELLIMAN

128 Sea Anchor Dr, Osprey, FL 34229

/2
Est $2,524,902 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

/54
$5,990,000 Open Sun 1PM - 3PM
- 4 Beds
- 5.5 Baths
- 5,397 Sq Ft
144 N Casey Key Rd, Osprey, FL 34229

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front

Joel Schemmel DOUGLAS ELLIMAN

144 N Casey Key Rd, Osprey, FL 34229
/2
$390,000 Sold Apr 15, 2025
- 1,334 Sq Ft
- $292/SF
- 21 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
441 N 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

Dawn Barnett EXIT KING REALTY

441 N Shore Dr, Osprey, FL 34229

/29
Est $2,035,345 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

/43
$620,000
- 3 Beds
- 2 Baths
- 2,298 Sq Ft
556 Crane Prairie Way, Osprey, FL 34229

Welcome to a beautiful residence where comfort, privacy, and functionality come together seamlessly. A paver driveway, tile roof, mature landscaping, and a charming paver walkway set the tone as you arrive, leading to an inviting French door entry framed by a transom window. Inside, tile floors stretch through the main living areas, beginning with a light-filled foyer adorned with a chandelier.

Joel Schemmel DOUGLAS ELLIMAN

556 Crane Prairie Way, Osprey, FL 34229
/2
$1,160,000 Sold Apr 15, 2025
- 1,787 Sq Ft
- $649/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
131 Tina Island Dr, Osprey, FL 34229

Welcome to your dream waterfront oasis! This exquisite 3-bedroom, 2-bathroom residence offers unparalleled water views and mesmerizing sunsets from the expansive pool deck. The generous outdoor living area is perfect for hosting gatherings or enjoying peaceful moments by the canal. The thoughtfully designed split-bedroom layout ensures privacy, making it ideal for accommodating guests or family

Sarah McGuire WHITE SANDS REALTY GROUP FL

131 Tina Island Dr, Osprey, FL 34229

/84
Est $1,150,117 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

/49
$544,700
- 2 Beds
- 2 Baths
- 1,875 Sq Ft
827 Placid Lake Dr, Osprey, FL 34229

This lot and location really stands out! Set back on a quiet street, on a beautifully landscaped oversized lot, and a huge lawn in the backyard with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, and Florida lifestyle. This is a rare opportunity... one of the least expensive

Stephen Hachey FLAT FEE MLS REALTY

827 Placid Lake Dr, Osprey, FL 34229
/2
$700,000 Sold Apr 15, 2025
- 2,504 Sq Ft
- $280/SF
- 69 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
521 Luminary Blvd, Osprey, FL 34229

This stunning Lee Wetherington home, in the prestigious Willowbend community of Osprey, showcases the natural beauty of Florida through its beautifully designed Stanford, rarely available floor plan. Home has a 22-kilowatt whole-house generator. Set against the backdrop of a sparkling lake, the residence features a great room, dining area, kitchen, dinette, owner’s suite all benefiting from one

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

521 Luminary Blvd, Osprey, FL 34229

/2
Est $213,186 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

/7
$115,000
570 Blackburn Point Rd Unit 13, Osprey, FL 34229

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! This rarely available slip can fit boats up to 9 ft in height and 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

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 13, Osprey, FL 34229
/2
$879,352 Sold Apr 15, 2025
- 1,937 Sq Ft
- $454/SF
- 14 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 402, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Photos are a representation of multiple floor plans in the building. Watch the most breathtaking sunsets from your private extra-large, screened-in balcony as you look out across the bay to the barrier island of Casey Key! Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. This

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 402, Osprey, FL 34229

/2
Est $658,628 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,695 Sq Ft
1192 Mallard Marsh Dr, Osprey, FL 34229

1192 Mallard Marsh Dr, Osprey, FL 34229

/95
$900,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 304, Osprey, FL 34229

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 304, Osprey, FL 34229
/2
$832,000 Sold Apr 14, 2025
- 1,988 Sq Ft
- $419/SF
- 178 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
14041 Bellagio Way Unit 313, Osprey, FL 34229

Welcome to the highly desirable community of The Villas at Osprey Harbor! This light and bright end unit with a private entrance is loaded with recent, tasteful updates including a fully renovated kitchen in 2022 with high end rift cut white oak custom cabinetry and a quartz breakfast bar, induction stove, updated baths, 24-by-24 porcelain tile, lighting, fans, fresh paint throughout, a coffee

Megan George PREMIER SOTHEBYS INTL REALTY

14041 Bellagio Way Unit 313, Osprey, FL 34229

/2
Est $600,527 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

/61
$325,000
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
116 Navigation Cir Unit 106, Osprey, FL 34229

Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

Pan Steele, GRI COLDWELL BANKER REALTY

116 Navigation Cir Unit 106, Osprey, FL 34229
/2
$275,000 Sold Apr 11, 2025
- 900 Sq Ft
- $306/SF
- 33 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
208 Pennsylvania Ave, Osprey, FL 34229

PRICED to SELL! Incredible Opportunity, Don\'t miss this one! Nice 3Br 2Ba single family home on large fenced corner lot in Osprey, Florida near Venice Beach. NO HOA! Large lot with plenty of space for additions, RV or Boat parking, swimming pool, etc. One of the best deals in the area! Turn-key and ready to move in, New paint

Stephen Hachey FLAT FEE MLS REALTY

208 Pennsylvania Ave, Osprey, FL 34229

/2
Est $820,112 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,433 Sq Ft
1030 Scherer Way, Osprey, FL 34229

1030 Scherer Way, Osprey, FL 34229

/37
$198,000 Open House 11/23
- 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
/2
$832,750 Sold Apr 10, 2025
- 1,937 Sq Ft
- $430/SF
- 27 Days On Market
- 3 Beds
- 2 Baths
- Built 2025
280 Hidden Bay Dr Unit 303, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan. Witness the most breathtaking sunsets from your private, extra-large screened-in balcony as you gaze out across the bay to the barrier island of Casey Key! Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 303, Osprey, FL 34229

/55
Est $965,956 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

/62
$785,500
- 4 Beds
- 3 Baths
- 2,314 Sq Ft
523 Habitat Blvd, Osprey, FL 34229

In the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting residence borders a sparkling lake with curb appeal emphasized by lush landscaping and a paver-accented driveway. This quality-built home is the desirable Ashley II floor plan, with an oversized 23-by-19-foot garage. Every detail in this home is addressed with remarkable style including double-door entry,

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

523 Habitat Blvd, Osprey, FL 34229
/2
$925,000 Sold Apr 10, 2025
- 2,166 Sq Ft
- $427/SF
- 31 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
280 Hidden Bay Dr Unit 401, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Under construction. The photos are a representation of multiple floor plans in the building. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. The gated, 12-acre resort-style community is nestled on the water’s edge of Little Sarasota Bay in Osprey. The final waterfront building

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 401, Osprey, FL 34229

/45
Est $656,794 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

/4
$42,500
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 10.5W x 6.5H. With valet boat service,

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
/2
$400,000 Sold Apr 08, 2025
- 1,574 Sq Ft
- $254/SF
- 115 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
4239 Expedition Way, Osprey, FL 34229

NEW PRICE AND PRICED TO SELL - THE ONLY AVAILABLE 2 CAR GARAGE UNIT LISTED IN THE COMMUNITY! Welcome to Bay Street Village, a highly sought-after gated condominium community in the heart of Osprey. This rarely available FIRST FLOOR, EXTENDED 2-car garage condo offers plenty of space for vehicles and gear, making it ideal for those with an active lifestyle. The beautiful home is being sold

Joe Cleary RE/MAX ALLIANCE GROUP

4239 Expedition Way, Osprey, FL 34229

/40
Est $744,581 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

/33
$760,000
- 5 Beds
- 4 Baths
- 3,395 Sq Ft
851 Placid Lake Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Your dream home is waiting for you! Enjoy a bright interior decorated with a neutral color palette. You'll love cooking in this kitchen, which includes a spacious center island and a sleek backsplash. Retreat to the spacious primary suite, designed with a good layout and a closet. The primary bathroom offers a separate tub and shower, double sinks,

Karen Albright OPENDOOR BROKERAGE LLC

851 Placid Lake Dr, Osprey, FL 34229
/2
$512,500 Sold Apr 07, 2025
- 2,147 Sq Ft
- $239/SF
- 34 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
1152 Beachcomber Ct Unit 15, Osprey, FL 34229

Coastal Living at its Finest! Discover this beautifully designed 3 bedroom, 2.5 bath townhouse in the desirable Blackburn Point Marina Community! Enjoy prime location just steps from the Intercoastal Waterway, the Gulf of Mexico, Blackburn State Park, the Blackburn Point Marina, and the beloved Casey Key Fish House and Tiki Bar along with the new Deep Lagoon Restaurant. Step inside to find a

Jennifer Bright BRIGHT REALTY

1152 Beachcomber Ct Unit 15, Osprey, FL 34229

/32
Est $619,011 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

/61
$474,900
- 3 Beds
- 2 Baths
- 1,883 Sq Ft
7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

Toy Coxey KW COASTAL LIVING

7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
/2
$290,000 Sold Apr 07, 2025
- 1,120 Sq Ft
- $259/SF
- 195 Days On Market
- 3 Beds
- 2 Baths
- Built 1957
427 Washington Ave, Osprey, FL 34229

One or more photo(s) has been virtually staged. Charming 3/2 Bungalow with Endless Possibilities with a freshly painted interiorStep into this delightful 3-bedroom, 2-bathroom bungalow and instantly feel at home. The large screened-in porch welcomes you with ample space for a cozy porch swing, where you can enjoy your morning coffee or evening cocktails while soaking in the serene

Kelly Jenkins KW COASTAL LIVING II

427 Washington Ave, Osprey, FL 34229

/11
Est $319,480 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,402 Sq Ft
217 Glenwood Ave, Osprey, FL 34229

217 Glenwood Ave, Osprey, FL 34229

/43
$689,000
- 4 Beds
- 2 Baths
- 2,145 Sq Ft
819 Shadow Bay Way, Osprey, FL 34229

A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting

Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

819 Shadow Bay Way, Osprey, FL 34229
/2
$559,500 Sold Apr 04, 2025
- 2,165 Sq Ft
- $258/SF
- 56 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
1219 Chalet Ct, 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 borders a wide greenbelt with tasteful landscaping that enhances its curb appeal. The enlarged lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1219 Chalet Ct, Osprey, FL 34229

/33
Est $2,776,222 Not Listed For Sale
- 4 Beds
- 7 Baths
- 8,763 Sq Ft
692 Oaks Creek Ct, Osprey, FL 34229

692 Oaks Creek Ct, Osprey, FL 34229

/24
$624,700
- Land
- 0.34 Acre
- $1,837,353 per Acre
458 N Shore Dr, Osprey, FL 34229

Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

Matthew Charland LLC GULF SHORES REALTY

458 N Shore Dr, Osprey, FL 34229

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