Osprey, FL Homes

/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

/37
Est $584,230 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,846 Sq Ft
514 Oak Bay Dr, Osprey, FL 34229

514 Oak Bay Dr, Osprey, FL 34229

/37
$5,300,000
- 4 Beds
- 5.5 Baths
- 5,087 Sq Ft
101 Osprey Point Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this magnificent luxury home with 4 bedrooms, 5 full and 1 half bath. Meticulously crafted with unparalleled attention to detail by Bo MacEwen, this residence exemplifies quality and refinement at every turn. From the moment you approach, this home's stately facade and impeccable

Steve Abbe COLDWELL BANKER REALTY

101 Osprey Point Dr, Osprey, FL 34229
/2
$520,000 Sold Feb 14, 2025
- 1,680 Sq Ft
- $310/SF
- 14 Days On Market
- 2 Beds
- 2 Baths
- Built 1997
555 Meadow Sweet Cir, Osprey, FL 34229

Rivendell is a unique neighborhood. You must see it to appreciate the quaint and friendly setting. This home is in the original "Cottages of Rivendell". From the canopy tree's lining the neighborhood to the uniqueness of the individual homes you will be impressed. ; This home has an efficient layout that lets you easily decorate and enjoy every space. Also no need to worry about the many

Jack Keller JACK KELLER INC

555 Meadow Sweet Cir, Osprey, FL 34229

/16
Est $347,279 Not Listed For Sale
- 2 Beds
- 2 Baths
- 967 Sq Ft
340 Pennsylvania Ave, Osprey, FL 34229

340 Pennsylvania Ave, Osprey, FL 34229

/67
$769,900
- 4 Beds
- 3 Baths
- 2,589 Sq Ft
826 Oak Briar Ln, Osprey, FL 34229

Welcome to this Impressive 4-bedroom, 3-bath pool home located in the highly desirable Park Trace Estates in Osprey, Florida — perfectly situated in a PRIME LOCATION between Sarasota, Nokomis, and Venice. Boasting over 3,000 sq. ft. under roof, this modern, updated ranch-style home is designed for indoor and outdoor living, featuring an open, split floor plan that flows seamlessly to the spacious

Peter LaSalle PREFERRED SHORE LLC

826 Oak Briar Ln, Osprey, FL 34229
/2
$3,335,000 Sold Feb 12, 2025
- 2,417 Sq Ft
- $1380/SF
- 7 Days On Market
- 3 Beds
- 3 Baths
- Built 1978
419 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 SOTHEBYS INTL REALTY

419 Yacht Harbor Dr, Osprey, FL 34229

/63
Est $1,197,696 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,048 Sq Ft
113 Harbor House Dr, Osprey, FL 34229

113 Harbor House Dr, Osprey, FL 34229

/61
$649,000
- 3 Beds
- 2.5 Baths
- 2,130 Sq Ft
51 Webb St, Osprey, FL 34229

***PRICE IMPROVEMENT***Location, Location, Location! Situated west of the trail in the heart of Osprey, this stunning 3-bedroom, 2-bathroom plus den ranch home is a rare find, just steps from Sarasota Bay. Enjoy a tranquil coastal lifestyle, with the Main Street fishing pier, Spanish Pointe Marina, Oscar Scherer State Park, and the renowned Pine View School for the Gifted close by. Surrounded by

Marina Myers FINE PROPERTIES

51 Webb St, Osprey, FL 34229
/2
$317,500 Sold Feb 07, 2025
- 1,244 Sq Ft
- $255/SF
- 5 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
128 Navigation Cir Unit 103, Osprey, FL 34229

This charming Florida condo is perfect for anyone seeking a full-time residence or a seasonal getaway. The unit is being sold furnished. Lovely, 2 bedrooms, 2 baths, attached single car garage. The Heron floor plan features an open concept kitchen with dining and great room. Easy access to the resort-style heated pool, fitness room, and club room. The property is comprised of two bedrooms

Tim Weller EXIT KING REALTY

128 Navigation Cir Unit 103, Osprey, FL 34229

/31
Est $365,414 Not Listed For Sale
- 2 Beds
- 2 Baths
- 874 Sq Ft
21 Shumard St, Osprey, FL 34229

21 Shumard St, Osprey, FL 34229

/35
$275,000
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
111 Woodland Place, Osprey, FL 34229

Property comes furnished.Rare, 1st floor condo in Pine Run. Unique layout with center outdoor solarium for peaceful retreat. This 2 bd, 2 bath offers lots of space and privacy. Large exp lanai and an outdoor eating area off kit. Beautiful newer luxury vinyl floors. New hot water heater, young air/heating unit. Nicely located carport and lots of storage. Pine Run has two pools, tennis and

Stephen Hachey FLAT FEE MLS REALTY

111 Woodland Place, Osprey, FL 34229
/2
$1,850,000 Sold Jan 31, 2025
- 4,361 Sq Ft
- $424/SF
- 31 Days On Market
- 5 Beds
- 4 Baths
- Built 2006
855 MacEwen Dr, Osprey, FL 34229

This stunning 5 bedroom, 4 bath residence, custom built by Wetherington, epitomizes refined living and sophisticated elegance. Nestled in The Oaks Clubside, it enjoys an incredible private setting, with no house or neighbors on one side. This home is large and spacious, with timeless design elements, creating an exquisite sanctuary. As you enter through the double leaded glass front doors, the

Steve Abbe COLDWELL BANKER REALTY

855 MacEwen Dr, Osprey, FL 34229

/18
Est $268,944 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 996 Sq Ft
248 Washington Ave, Osprey, FL 34229

248 Washington Ave, 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
$1,650,000 Sold Jan 31, 2025
- 5,399 Sq Ft
- $306/SF
- 12 Days On Market
- 5 Beds
- 5.5 Baths
- Built 1992
676 Eagle Watch Ln, Osprey, FL 34229

Florida living at its finest! You'll find this lovely home tucked away on a cul-de-sac in the luxurious community known as The Oaks. This amazing custom-built home features 5 bedrooms, 5.5 bathrooms and 5,399 sq. ft. of fabulous living space, combining comfort with elegance! Upon entering you are greeted by the formal living room with high ceilings, crown molding, large sliding glass doors and

Jamie Mullis COLDWELL BANKER REALTY

676 Eagle Watch Ln, Osprey, FL 34229

/50
Est $896,049 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,680 Sq Ft
3603 N Point Rd Unit 501, Osprey, FL 34229

3603 N Point Rd Unit 501, Osprey, FL 34229

/18
$315,000
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
4226 Frontier Ln Unit 103, Osprey, FL 34229

BEING SOLD FULLY FURNISHED AND FULLY EQUIPPED - TURNKEY !! Please check the 3D matter port tour. Start enjoying the Florida lifestyle at Bay Street! The spacious floor plan makes great use of space with two bedrooms, two baths, and an attached one car garage. Oversized windows allow Florida sunshine to fill this home with light. Beautiful 18x18 ceramic floor tile in the main living areas. Kitchen

Carlos Saramago EXIT KING REALTY

4226 Frontier Ln Unit 103, Osprey, FL 34229
/2
$1,450,000 Sold Jan 31, 2025
- 4,614 Sq Ft
- $314/SF
- 193 Days On Market
- 5 Beds
- 5.5 Baths
- Built 2003
738 N MacEwen Dr, Osprey, FL 34229

Imagine how you’d like to live the ultimate Florida lifestyle. Your vision can become a reality in this 5 bedroom, 5.5 bath two story home in The Oaks Clubside. Currently unfurnished, you just need to pack your bags, bring your own style and make it your own. Set back on a cul-de-sac lot, with gorgeous lake and golf views, the floor plan offers flexibility for the space to be used by residents

Steve Abbe COLDWELL BANKER REALTY

738 N MacEwen Dr, Osprey, FL 34229

/35
Est $760,228 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,721 Sq Ft
579 Oak Bay Dr, Osprey, FL 34229

579 Oak Bay Dr, Osprey, FL 34229

/9
$145,900
- Land
- 0.18 Acre
- $810,556 per Acre
0 Cordes St Unit MFRN6137674, Osprey, FL 34229

Location, Location, Location.Great corner lot in a very quiet neighborhood, perfect to build your dream house. 10 minutes to Siesta beach and Nokomis beach. Pine View School, Nokomis School and Venice High school are within few miles. For outdoor activities Oscar Scherer Park and Legacy Trial are also very close. This area is surrounded by good restaurants and great shopping centers. Lot is

Zuzanna Kacprzak CENTURY 21 SCHMIDT REAL ESTATE

0 Cordes St Unit MFRN6137674, Osprey, FL 34229
/2
$900,000 Sold Jan 31, 2025
- 2,855 Sq Ft
- $315/SF
- 281 Days On Market
- 3 Beds
- 3 Baths
- Built 1997
201 Saint James Park, Osprey, FL 34229

Welcome home to your sanctuary located behind the gates of the Exclusive Oaks Country Club. This corner lot in SAINT JAMES PARK is situated close to the CLUB, TENNIS, and all the amenities the community has to offer. As you approach the home the lush landscape and stunning trees capture your attention. Enter through the double front door to a serene view of the mature landscaping and view of the

Tina Timmons ROSEBAY INTERNATIONAL REALTY, INC

201 Saint James Park, Osprey, FL 34229

/25
Est $561,699 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,981 Sq Ft
543 Meadow Sweet Cir, Osprey, FL 34229

543 Meadow Sweet Cir, 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 SOTHEBYS INTL REALTY

1216 N Casey Key Rd, Osprey, FL 34229
/2
$435,000 Sold Jan 30, 2025
- 2,055 Sq Ft
- $212/SF
- 106 Days On Market
- 3 Beds
- 3 Baths
- Built 2001
393 N Point Rd Unit 302, Osprey, FL 34229

Enter through the secure foyer and take one of the two private elevators to the third floor where you will find this charming 3 bedroom (one is currently being used as a den/office and has the convenience of a built-in Murphy bed!), 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and spacious. Carefully updated and

Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 302, Osprey, FL 34229

/2
Est $984,513 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,258 Sq Ft
127 Turquoise Ln, Osprey, FL 34229

127 Turquoise Ln, Osprey, FL 34229

/59
$774,900
- 3 Beds
- 2 Baths
- 2,171 Sq Ft
866 Placid Lake Dr, Osprey, FL 34229

Immerse yourself in the blissful lifestyle located in the Woodlands of Rivendell, where this beautifully appointed home awaits. Situated within a community renowned for its expansive green spaces, parks, 24 shimmering lakes, proximity to Oscar Scherer State Park, heated community pool and nearby Pine View School, this residence offers a truly exceptional living experience. This enchanting

Justin Brunswick KELLER WILLIAMS ON THE WATER S

866 Placid Lake Dr, Osprey, FL 34229
/2
$1,200,000 Sold Jan 27, 2025
- 3,906 Sq Ft
- $307/SF
- 212 Days On Market
- 4 Beds
- 5.5 Baths
- Built 1989
639 Eagle Watch Ln, Osprey, FL 34229

You won’t find a home like this elegant 4 bedroom, 5.5 bath beauty every day. Situated on a beautiful lot in The Oaks Clubside, it offers privacy and stunning views overlooking the lake out to the #7 of the Heron Course. The quiet street ends in a cul-de-sac. Inside you will find a spacious floor plan that is anything but cookie-cutter. This home has a 4th bedroom above the garage, perfect as a

Steve Abbe COLDWELL BANKER REALTY

639 Eagle Watch Ln, Osprey, FL 34229

/64
Est $290,345 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
224 Woodland Dr, Osprey, FL 34229

224 Woodland Dr, Osprey, FL 34229

/95
$2,795,000
- 4 Beds
- 3.5 Baths
- 3,953 Sq Ft
49 Osprey Point Dr, Osprey, FL 34229

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

Jonathan Abrams MICHAEL SAUNDERS & COMPANY

49 Osprey Point Dr, Osprey, FL 34229
/2
$2,100,000 Sold Jan 24, 2025
- 3,896 Sq Ft
- $539/SF
- 140 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1989
627 Eagle Watch Ln, Osprey, FL 34229

**EXQUISITELY DESIGNED and BRILLIANTLY RENOVATED, CUSTOM GOLF COURSE ESTATE with SPECTACULAR WATER VIEW** is situated on the Interior HERON GOLF COURSE and is located on a tranquil, cul-de-sac street behind the Secure Gates of The Oaks Country Club neighborhood. Framed by stunning Grand Oaks, your approach will only be enhanced upon entering through the grand double doors and gazing out across

Mark Lyda GENEROUS PROPERTY

627 Eagle Watch Ln, Osprey, FL 34229

/41
Est $528,039 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,868 Sq Ft
541 Meadow Sweet Cir, Osprey, FL 34229

541 Meadow Sweet Cir, Osprey, FL 34229

/64
$799,000
- 4 Beds
- 3 Baths
- 2,678 Sq Ft
608 Crane Prairie Way, Osprey, FL 34229

One or more photo(s) has been virtually staged. Exceptional Opportunity on this Newly Priced Gem with stunning views and privacy! Discover your dream home in this stunning 2,678 square foot Wyndham model by Lee Wetherington, one of the largest in the maintenance-free community of Willowbend in Osprey. The owner has added improvements in excess of $150K since their purchase and has been lovingly

Linda Williams GULF SHORES REALTY

608 Crane Prairie Way, Osprey, FL 34229
/2
$325,000 Sold Jan 17, 2025
- 623 Sq Ft
- $522/SF
- 0 Days On Market
- 1 Bed
- 1 Bath
- Built 1990
51 MacEwen Dr Unit 20, Osprey, FL 34229

**BEAUTIFUL VIEW FROM THIS 2ND STORY, RENOVATED EFFICIENCY CONDO UNIT WITH BALCONY OVERLOOKING THE OAKS CLUBHOUSE ACROSS EXPANSIVE POND WITH FOUNTAIN** THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where

Mark Lyda GENEROUS PROPERTY

51 MacEwen Dr Unit 20, Osprey, FL 34229

/59
Est $1,002,841 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,811 Sq Ft
384 S Creek Ct, Osprey, FL 34229

384 S Creek Ct, Osprey, FL 34229

/61
$1,395,000
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
3603 N Point Rd Unit 702, Osprey, FL 34229

**MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 702, Osprey, FL 34229
/2
$1,222,500 Sold Jan 17, 2025
- 3,020 Sq Ft
- $405/SF
- 25 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 201, Osprey, FL 34229

Welcome to Unit #201 in the exclusive Bellagio Harbor Village, where luxury meets the serene beauty of Florida’s Gulf Coast! Nestled in a prime location in Osprey, this spacious 3-bedroom, 3.5-bathroom with study condo offers nearly 3,000 sq. ft. of elegant living space designed with comfort and sophistication in mind. This luxury penthouse is currently the only unit that includes a 50 ft Boat

Brian Wood COMPASS FLORIDA LLC

14021 Bellagio Way Unit 201, Osprey, FL 34229

/99
Est $753,713 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,330 Sq Ft
801 Oak Briar Ln, Osprey, FL 34229

801 Oak Briar Ln, Osprey, FL 34229

/26
$224,900
- Land
- 0.30 Acre
- $749,667 per Acre
0 Sarabay Rd, Osprey, FL 34229

Empty residential lot, desirably located in Osprey, Sarasota County. This prime piece of land offers a fantastic opportunity to build your dream home in a sought-after neighborhood. Enjoy the charm of Osprey, with its proximity to beautiful beaches, top-rated schools, shopping, dining, and outdoor recreation. Don’t miss out on this exceptional investment in a growing community!Location is

Marta Marszalek CHARLES RUTENBERG REALTY INC

0 Sarabay Rd, Osprey, FL 34229
/2
$579,000 Sold Jan 16, 2025
- 2,165 Sq Ft
- $267/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 2003
1327 Thornapple 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 borders a greenbelt and preserve setting and 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

Tamara Currey PREMIER SOTHEBYS INTL REALTY

1327 Thornapple Dr, Osprey, FL 34229

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