Osprey, FL Homes

/75
$1,649,000
- 4 Beds
- 4 Baths
- 4,001 Sq Ft
75 Osprey Point Dr, Osprey, FL 34229

Welcome to 75 Osprey Point, a residence that epitomizes timeless elegance and thoughtful design within the prestigious Oaks Bayside. On two expansive lots totaling over three-quarters of an acre, this architectural estate was originally designed by renowned architect Bo MacEwen, the visionary behind The Oaks iconic clubhouse. A harmonious blend of traditional sophistication and modern updates

Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

75 Osprey Point Dr, Osprey, FL 34229
/2
$770,000 Sold Nov 14, 2024
- 1,943 Sq Ft
- $396/SF
- 401 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
232 Hidden Bay Dr Unit 602, Osprey, FL 34229

Live on the TOP FLOOR & ENJOY UNBELIEVABLE WATER & SUNSET VIEWS ALL YEAR round with an air-conditioned sunroom overlooking the water. IMPACT WINDOWS/DOORS for peace of mind. Seller relocation is your lucky day with this PRICE IMPROVED, partially furnished penthouse condo.A 3 Bedroom, 2 Bath Baypoint Vista Condo just under 2000 sqft. The sprawling open floor plan showcases a

Kelly Pankiw ENGEL & VOELKERS VENICE DOWNTOWN

232 Hidden Bay Dr Unit 602, Osprey, FL 34229

/100
Est $1,169,455 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,215 Sq Ft
328 Pine Ranch Trail, Osprey, FL 34229

328 Pine Ranch Trail, Osprey, FL 34229

/61
$247,400 Open Sat 11AM - 1PM
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
109 Woodland Place, Osprey, FL 34229

Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community in Osprey, Florida. This charming 2-bedroom, 2-bathroom condominium offers 1,223 square feet of thoughtfully designed living space, seamlessly blending comfort with the beauty of its environment. As you enter, you’ll be greeted by soaring ceilings and an open floor plan that

Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229
/2
$920,000 Sold Nov 07, 2024
- 2,888 Sq Ft
- $319/SF
- 137 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
1193 Lost Creek Ct, Osprey, FL 34229

One or more photo(s) has been virtually staged. IMPROVED PRICE!! Beautiful 4BR/3BA/3 Car Garage Pool Home located in The Woodlands of Rivendell. This gorgeous all on one floor home is surrounded by lush natural beauty with expansive views of a large sparkling lake and a beautiful extensive preserve. This home features a newer tile roof, two newer HVAC units and a Pebble-Tec pool with a gorgeous

Jay Mitchell COLDWELL BANKER REALTY

1193 Lost Creek Ct, Osprey, FL 34229

/54
Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,168 Sq Ft
871 MacEwen Dr, Osprey, FL 34229

871 MacEwen Dr, Osprey, FL 34229

/62
$449,900
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
2251 Jessie Harbor Dr, Osprey, FL 34229

**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

Mark Lyda GENEROUS PROPERTY

2251 Jessie Harbor Dr, Osprey, FL 34229
/2
$445,000 Sold Nov 06, 2024
- 1,391 Sq Ft
- $320/SF
- 13 Days On Market
- 2 Beds
- 2 Baths
- Built 2006
2267 Jessie Harbor Dr Unit 2103, Osprey, FL 34229

Discover a Rare WATERFRONT Gem in Osprey! Spacious 2-Bedroom and 2 Full Bath Villa with attached Garage in a small, well-maintained gated community. Blackburn Harbor Waterfront Villas are nestled in a super-convenient spot between Venice and Sarasota just west of 41 with direct water access to the Intercoastal Waterway and the Gulf of Mexico. This light-filled home offers beautiful water

Katie McNulty BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

2267 Jessie Harbor Dr Unit 2103, Osprey, FL 34229

/65
Est $1,946,121 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,327 Sq Ft
482 E MacEwen Dr, Osprey, FL 34229

482 E MacEwen Dr, Osprey, FL 34229

/69
$2,495,000
- 4 Beds
- 4 Baths
- 2,572 Sq Ft
312 Yacht Harbor Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a 6-foot depth at mean low tide, the marina can accommodate 175 boats owned by

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

312 Yacht Harbor Dr, Osprey, FL 34229
/2
$295,000 Sold Oct 29, 2024
- 1,325 Sq Ft
- $223/SF
- 2 Beds
- 2 Baths
- Built 1979
105 Woodland Place, Osprey, FL 34229

Welcome to your own personal oasis at 105 Woodland Place! This 2-bedroom, 2-bathroom home is a delightful blend of comfort and style, boasting a generous 1325 square feet of living space. As you step inside, you'll be captivated by the cleverly opened-up floor plan, creating a seamless flow throughout the home. Every room beckons you to step outside and embrace the lush surroundings, as each

Stellar Non-Member Agent Stellar Non-Member Office

105 Woodland Place, Osprey, FL 34229

/64
Est $346,776 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
112 Woodland Place, Osprey, FL 34229

112 Woodland Place, Osprey, FL 34229

/43
$695,000
- 3 Beds
- 2 Baths
- 2,145 Sq Ft
819 Shadow Bay Way, Osprey, FL 34229

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 three bedrooms, formal dining room, den, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting front porch is

Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

819 Shadow Bay Way, Osprey, FL 34229
/2
$750,000 Sold Oct 29, 2024
- 2,336 Sq Ft
- $321/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
1228 Chalet Ct, Osprey, FL 34229

Experience breathtaking views from this magnificent Lee Wetherington Ashley II floor plan residence, overlooking a picturesque, lush greenbelt. Embrace the tranquility of daily wildlife sightings in this desired private exposure setting. The intelligent design of this home is not only visually striking but also functional, with meticulous attention to detail and remarkable style evident

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1228 Chalet Ct, Osprey, FL 34229

/30
Est $152,258 Not Listed For Sale
- 1 Bed
- 1 Bath
- 586 Sq Ft
751 Pine Run Dr Unit 751, Osprey, FL 34229

751 Pine Run Dr Unit 751, Osprey, FL 34229

/87
$3,275,000
- 3 Beds
- 4.5 Baths
- 2,572 Sq Ft
135 Tina Island Dr, Osprey, FL 34229

If you are ready to retreat to paradise, look no more. This home is amazing. Located in a very desirable area in Sorrento Shores, Osprey is on a 200-foot, wide canal frontage. You can enjoy the scenic water and exotic palms through almost every window. The main area, the living area, was built and completed in 2011, and it is beautifully situated on the second floor. All windows are

Regina Melman RE/MAX PALM REALTY OF VENICE

135 Tina Island Dr, Osprey, FL 34229
/2
$575,000 Sold Oct 28, 2024
- 2,151 Sq Ft
- $267/SF
- 15 Days On Market
- 3 Beds
- 2 Baths
- Built 1996
584 Meadow Sweet Cir, Osprey, FL 34229

Welcome to your new slice of serenity! Introducing a charming 3-bedroom, 2-bathroom home in the Cottages of Rivendell that promises both comfort and convenience. As you pull into the neighborhood you will feel welcomed and in awe of the beautiful trees and white picket fences lining the streets. Maintenance Free neighborhood! Pride in ownership is apparent as you enter the home. Whether you're

Richard Tritschler RE/MAX ALLIANCE GROUP

584 Meadow Sweet Cir, Osprey, FL 34229

/50
Est $546,805 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
529 Meadow Sweet Cir, Osprey, FL 34229

529 Meadow Sweet Cir, Osprey, FL 34229

/92
$959,000
- 3 Beds
- 2 Baths
- 2,216 Sq Ft
21 Bayhead Ln, Osprey, FL 34229

This incredible newly updated house with many upgrades and amenities is the home you have been waiting for! Ideally located in the beautiful Oaks Preserve between Siesta Key and Casey Key, the private enclave is in a shaded neighborhood where residents enjoy the canopied surroundings and friendly atmosphere. Minutes from shopping, beaches and cultural arts, this maintenance free home sits on a

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

21 Bayhead Ln, Osprey, FL 34229
/2
$660,000 Sold Oct 28, 2024
- 2,695 Sq Ft
- $245/SF
- 191 Days On Market
- 3 Beds
- 3 Baths
- Built 2002
1192 Mallard Marsh Dr, Osprey, FL 34229

Rivendell offers the perfect blend of Community living and privacy. This home is situated on a premier lot with a spectacular view of the lake in the back and the open green space across the street from the front yard.The open split floor plan of this home creates a spacious atmosphere ,perfect for both comfortable living and entertaining.Woodlands of Rivendell features a community play

Marie Fogarty M H FOGARTY AND COMPANY LLC

1192 Mallard Marsh Dr, Osprey, FL 34229

/68
Est $938,443 Not Listed For Sale
- 6 Beds
- 3 Baths
- 3,982 Sq Ft
1081 Scherer Way, Osprey, FL 34229

1081 Scherer Way, Osprey, FL 34229

/62
$850,000
- 3 Beds
- 3 Baths
- 2,203 Sq Ft
393 N Point Rd Unit 603, Osprey, FL 34229

Enjoy breathtaking views of the Gulf of Mexico, Little Sarasota Bay and the Intercoastal waterway from your living room, bedroom, or lanai. The sunsets are absolutely gorgeous from this 3 bedroom, 3 bath condo, which offers all the views and the safety of a building on the mainland with easy access to the Tamiami Trail and Route 75. Stroll out of your building that has no steps to the pool,

Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 603, Osprey, FL 34229
/2
$625,000 Sold Oct 25, 2024
- 2,078 Sq Ft
- $301/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
522 Pine Ranch Rd E, Osprey, FL 34229

Live the lifestyle you deserve and move right in to this beautiful 3 bedroom 2 bath pool home in the boutique enclave community of Bay Oaks Estates. This meticulously cared for home will let you enjoy the indoor - outdoor Florida living you have been longing for. This home is situated on one of the nicest lots in Bay Oaks with private community owned space in the back and open space with no house

Jill Friedman COLDWELL BANKER REALTY

522 Pine Ranch Rd E, Osprey, FL 34229

/42
Est $623,754 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,165 Sq Ft
1312 Copperwood Dr, Osprey, FL 34229

1312 Copperwood Dr, Osprey, FL 34229

/82
$4,195,000
- 4 Beds
- 6 Baths
- 9,081 Sq Ft
854 MacEwen Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. **SELLER WILL PAY 100% OF THE MANDATORY SOCIAL MEMBERSHIP – WORTH $80,000 – IF CLOSING BY JUNE 2ND, 2025** NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths +

Mark Lyda GENEROUS PROPERTY

854 MacEwen Dr, Osprey, FL 34229
/2
$875,000 Sold Oct 25, 2024
- 2,176 Sq Ft
- $402/SF
- 114 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1997
510 Old Venice Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. This is the one you've been waiting for! Nestled on approximately 3 acres, this cherished family estate, spanning generations, awaits its next chapter. Situated opposite the esteemed Pine View School for the Gifted, ranked #1 High School in Florida and #18 High School nationally, this unique parcel blends country charm with coastal allure. Winding

Daniel Jasmer FINE PROPERTIES

510 Old Venice Rd, Osprey, FL 34229

/38
Est $703,233 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,269 Sq Ft
615 Crane Prairie Way, Osprey, FL 34229

615 Crane Prairie Way, Osprey, FL 34229

/50
$749,000
- 4 Beds
- 3 Baths
- 2,767 Sq Ft
524 Oak Bay Dr, Osprey, FL 34229

++No Hurricane damage or water intrusion from resent storms. ++ Charming Pool Home with Luxurious Upgrades in Bay Oaks Estates. One of the largest homes in this community. Welcome to your dream home! Nestled in a cul-de-sac and less than 10 miles from Siesta Key Beach or Nokomis Beach. This stunning four-bedroom, three-bathroom residence offers the perfect blend of comfort, convenience, and

Frank Zeckel COLDWELL BANKER REALTY

524 Oak Bay Dr, Osprey, FL 34229
/2
$910,000 Sold Oct 23, 2024
- 2,614 Sq Ft
- $348/SF
- 37 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
919 Eagle Isle Ct, Osprey, FL 34229

Introducing a captivating luxury home situated on the serene and private cul-de-sac of Eagle Isle Court, within the coveted Woodlands of Rivendell community. This extraordinary residence, with a stunning outdoor living space, embodies the perfect fusion of sophistication, comfort, and natural splendor. Upon entering the grand foyer, you’re greeted by exquisite flooring, lofty ceilings,

Ryan Skrzypkowski COLDWELL BANKER REALTY

919 Eagle Isle Ct, Osprey, FL 34229

/43
Est $534,822 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

/55
$915,000 Open Sat 12PM - 2PM
- 3 Beds
- 4 Baths
- 3,183 Sq Ft
650 Crane Prairie Way, Osprey, FL 34229

**Discover Your Dream Home at 650 Crane Prairie Way, Osprey, FL 34229**Welcome to your tranquil retreat in the heart of Osprey, Florida. This stunning oasis, nestled in the desirable Willowbend community, offers a perfect blend of luxury and natural beauty. Built in 2005, this exquisite home spans 3,183 square feet, providing ample space for both relaxation and entertaining. Imagine waking up

Cheri Castro KELLER WILLIAMS ON THE WATER

650 Crane Prairie Way, Osprey, FL 34229
/2
$850,000 Sold Oct 23, 2024
- 2,594 Sq Ft
- $328/SF
- 53 Days On Market
- 3 Beds
- 3 Baths
- Built 2003
401 N Point Rd Unit 601, Osprey, FL 34229

Don’t miss out on this incredible opportunity! Located on the north side of building III in Meridian, and offering beautiful views, this 3 bedroom, 3 bath residence with office/den, is priced to sell! Freshly painted, and with new bedroom carpeting, this unit is clean, spacious and bright. Bring your furnishings, move right in and begin living the luxury condo lifestyle you’ve always dreamed

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 601, Osprey, FL 34229

/37
Est $899,499 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

/94
$1,395,000
- 3 Beds
- 3 Baths
- 3,029 Sq Ft
393 N Point Rd Unit 801, Osprey, FL 34229

Rare in every way, this 3 bedroom, 3 bath penthouse, with private two car garage, is only one of six units in Meridian that enjoys this incredible floor plan. The elegant interior is punctuated by SPECTACULAR VIEWS. This residence provides everything you could desire for a luxury lifestyle in Coastal Florida. A former model, it has been lovingly maintained, and beautifully updated. From the

Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 801, Osprey, FL 34229
/2
$1,775,000 Sold Oct 22, 2024
- 3,912 Sq Ft
- $454/SF
- 152 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1989
165 Sugar Mill Dr, Osprey, FL 34229

This 4 bedroom, 4.5 bath home in The Oaks Bayside has been continuously updated and redecorated over the past several years, making it a pristine, elegant showcase. This is the perfect home for the refined country club lifestyle you seek to live. As you enter the new paver circular driveway, with three car side entry garage, it is evident how special this house is. Ideally situated on a private

Steve Abbe COLDWELL BANKER REALTY

165 Sugar Mill Dr, Osprey, FL 34229

/29
Est $2,237,288 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

/79
$515,000
- 2 Beds
- 2 Baths
- 1,862 Sq Ft
328 Woods Point Rd, Osprey, FL 34229

WEST OF TRAIL coastal living at its best! You’ve found it in this fully updated, one-story, end-unit villa in Osprey’s highly coveted, MAINTENANCE-FREE & pet-friendly Blackburn Point Woods! The Blackburn Point Woods enclave consists of 44 single-family attached homes ingeniously carved into 15 acres of a naturally wooded setting. Fully re-designed landscaping, tropical greenery and a paver

Priscilla Adams COMPASS FLORIDA LLC

328 Woods Point Rd, Osprey, FL 34229
/2
$580,000 Sold Oct 17, 2024
- 1,482 Sq Ft
- $391/SF
- 23 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
216 Shoreland Dr, Osprey, FL 34229

Key West Home completely redone in 2023 listed at $30K Under Recent Appraisal! 3 Bedroom /2 Bath plus Office/Den with High End Finishes. The interior and exterior blend seamlessly with a screened lanai across the entire front of the home with French doors into all front facing rooms. It feels as though you’re in a treehouse.Take your Kayaks & Canoes across the street to Shoreland Park

Dennis Schulte MICHAEL SAUNDERS & COMPANY

216 Shoreland Dr, Osprey, FL 34229

/84
Est $1,271,134 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

/46
$760,000
- 3 Beds
- 2 Baths
- 1,799 Sq Ft
14041 Bellagio Way Unit 214, Osprey, FL 34229

One or more photo(s) has been virtually staged. Welcome home to Osprey, FL, a true gem nestled between Sarasota and Venice. Nearby attractions include the Marie Selby Gardens at Historic Spanish Point, award-winning Oscar Scherer State Park, Blackburn Point Park and Casey Key nearby. Experience luxury living in this 3-bedroom, 2 bath condo at the Villas of Osprey Harbor Village featuring

Veronica Lee FINE PROPERTIES

14041 Bellagio Way Unit 214, Osprey, FL 34229

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