16 listings found
851 PLACID LAKE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 4 Bath · 3,395 SqFt · $218/SqFt
Days on Market: 1
Cumulative Days on Market: 127
County: Sarasota
Subdiv/Community Name: Rivendell
Legal Subdivision Name: RIVENDELL THE WOODLANDS
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes
Community Pool: Yes
Welcome to this stunning, recently remodeled 5-bedroom, 4-bath two-story residence nestled within the highly sought-after Woodlands at Rivendell in Osprey, Florida. Set on a prime corner lot with serene water and nature views, this expansive 3,400-square-foot home delivers a refined blend of elegance, comfort, and the very best of the Florida luxury lifestyle—where mornings begin with peaceful water views, afternoons are spent poolside under the Florida sun, and evenings unfold in effortless indoor-outdoor elegance. Thoughtfully designed for resort-style indoor-outdoor living, the home features a screened-in pool and spa, with the spa gracefully cascading into the main pool, creating your own private ... Read more....»
919 TRANQUILITY CIRCLE CIRCLE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 2,854 SqFt · $298/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: North Creek Estates
Legal Subdivision Name: NORTH CREEK ESTS
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle. This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with granite countertops, island, and gas range—perfect for entertaining. The great room and lanai seamlessly connect to the sparkling pool, creating a private retreat with creek views. The luxurious Primary suite is ... Read more....»
319 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,551 SqFt · $294/SqFt
Days on Market: 9
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2000
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Welcome to your dream home in a prime location, positioned near A-rated schools such as Pine View, world-class beaches, premier shopping and exceptional dining. This spacious four-bedroom, three-bath residence offers almost 2,600 square feet of living space, blending comfort and elegance at every turn. The home is filled with beautiful finishing touches, creating a warm yet sophisticated ambiance. Some updates that have been done are whole house re-pipe, hurricane shutters, water heater, custom closets, solar panels, air conditioner 2024, roof 2025 and the list goes on. This one is must-see! The oversized garage with a sought-after side-load entry and doors ... Read more....»
1303 THORNAPPLE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 1,929 SqFt · $362/SqFt
Days on Market: 33
County: Sarasota
Subdiv/Community Name: Willowbend
Legal Subdivision Name: WILLOWBEND PH 1
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW Barrel Tile ROOF (Nov 2025) in Sought After Willowbend----ideally located near the Community Fitness Center, Pool, Pickleball Courts & Playground.....Generous-Sized Living Spaces with Bright/Spacious Open Floor Plan affording ease of INDOOR/OUTDOOR LIVING where you will Enjoy Morning Coffees and Twilight Sunsets lounging in Expansive Screened Lanai.....Elegantly Updated Throughout, including: Cabinets, Countertops, Flooring, Crown Molding and Ceiling Fixtures---other recent improvements include Garage Door, Pool Heater & Retractable Solar Shade. Abundance of Storage, Built-ins and Closets.......Willowbend is a HIGHLY DESIRED boutique community ... Read more....»
1042 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,781 SqFt · $784/SqFt
Days on Market: 34
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: PALMER
Year built: 1995
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay breezes and water views, while majestic oaks and lush tropical landscaping create a timeless Old Florida setting. Launch your kayak from the backyard, walk your private beach access every morning, and enjoy both sunrises and sunsets from ... Read more....»
919 TRANQUILITY CIRCLE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 2,854 SqFt · $350/SqFt
Days on Market: 41
County: Sarasota
Subdiv/Community Name: North Creek Estates
Legal Subdivision Name: NORTH CREEK ESTS
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
AMAZING PRICE ADJUSTMENT. RARE OPPORTUNITY to own this stunning former John Cannon model home PLUS the adjacent buildable lot on peaceful Tranquility Circle. This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. The vacant lot also has it's own access. Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with granite countertops, island, and gas range—perfect for entertaining. The great room and lanai seamlessly connect to the ... Read more....»
403 LONGBOW TRAIL
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,770 SqFt · $432/SqFt
Days on Market: 61
County: Sarasota
Subdiv/Community Name: Pine Ranch
Legal Subdivision Name: PINE RANCH
Year built: 1978
Garage: Yes 3 vehicles
Private Pool: Yes
Lot Size (in acres): 2.00
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 comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. ... Read more....»
120 CANDYCE DRIVE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,103 SqFt · $356/SqFt
Days on Market: 43
County: Sarasota
Subdiv/Community Name: Sorrento Shores
Legal Subdivision Name: SORRENTO SHORES
Year built: 1962
Garage: Yes 4 vehicles
Private Pool: Yes
This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation ... Read more....»
327 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,935 SqFt · $289/SqFt
Days on Market: 29
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
LOOK NO FURTHER! This immaculate, lake-view four-bedroom/ three-bath home is MOVE-IN READY. Complete with a NEW 60K Tile ROOF, PGT Impact Windows throughout and new A/C (2024)! Freshly painted interior from top to bottom with Regal select Benjamin Moore paint, sparkling epoxy garage floor, New GE 5 burner range with Crisp mode, walk in pantry, beautifully Updated landscaping, new modern outdoor remote controlled ceiling fans along with outdoor shower. With just under 3,000 square feet of indoor living space combined with another 1,000 sq feet of extra large patio, this is the ideal entertainment home. Complete with hardwood floors and tile throughout, add your choice of ... Read more....»
137 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 3,303 SqFt · $431/SqFt
Days on Market: 30
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: THE OAKS BAYSIDE
Year built: 1996
Garage: Yes 2 vehicles
Private Pool: Yes
Although built in the 20th century, this home looks as authentic as the French manor house it was modeled after. The façade features a soft, light-colored stucco exterior accented by rustic stonework, creating a warm and inviting presence. Gracefully arched windows and classic dormers enhance the wooden shingle roof, which is crowned by two stately chimneys that add to the home's old-world charm. A gently curved brick-bordered walkway leads through a beautifully landscaped front yard, where manicured shrubs and vibrant flowering plants frame the path to the entrance. Bathed in sunlight under a clear blue sky, the entire scene feels ... Read more....»
312 YACHT HARBOR DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 4 Bath · 2,572 SqFt · $894/SqFt
Days on Market: 107
County: Sarasota
Subdiv/Community Name: Southbay Yacht & Racquet Club
Legal Subdivision Name: SOUTHBAY YACHT & RACQUET CLUB
Year built: 1978
Garage: Yes 3 vehicles
Private Pool: Yes
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 six-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $612 per quarter and it’s also affordable to keep your boat in a slip that includes water and electric. With the Southbay neighborhood in your backyard ... Read more....»
101 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 5,087 SqFt · $983/SqFt
Days on Market: 1
County: Sarasota
Subdiv/Community Name: The Oaks
Legal Subdivision Name: THE OAKS
Year built: 1985
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a ... Read more....»
133 OSPREY POINT DRIVE
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 3,679 SqFt · $367/SqFt
Days on Market: 59
County: Sarasota
Subdiv/Community Name: Oaks
Legal Subdivision Name: OAKS
Year built: 1987
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer kitchen (with Thermador appliances) and all freshly painted. This 4 bedroom, 3 bathroom plus bonus room house is in ideal size to maintain while fully enjoying with your family and guests. All rooms overlook the pool area with large windows allowing lots of natural light yet still completely private. The large primary bedroom has two walk-in closets and ... Read more....»
471 PARK TRACE BOULEVARD
OSPREY FL 34229
Residential / Single Family Residence
4 Bed · 3 Bath · 2,267 SqFt · $308/SqFt
Days on Market: 179
County: Sarasota
Subdiv/Community Name: Park Trace Estates
Legal Subdivision Name: PARK TRACE ESTATES
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant community feel with low HOA fees. It is situated on an over-sized corner lot, with exceptional lake-views, and just moments from several pristine beaches, the scenic Legacy Trail, Pineview School plus other nearby “A-Rated” public schools, and Oscar Scherer State Park. Being centrally located, you will enjoy all the amenities Sarasota and Venice have, including ... Read more....»
110 PINE AVENUE
OSPREY FL 34229
Residential / Single Family Residence
3 Bed · 2 Bath · 2,058 SqFt · $340/SqFt
Days on Market: 243
County: Sarasota
Subdiv/Community Name: Osprey Avenue Sub
Legal Subdivision Name: SAUNDERS V A RESUB
Year built: 1977
Garage: Yes 2 vehicles
Private Pool: Yes
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 paddleboard from a few steps away into Sarasota Bay, explore Mid night pass, Siesta Beach, nearby Bay Preserve at Osprey and Historic Spanish Point, close to Oscar Scherer State Park, Casey Key, Nokomis Beach. The large backyard offers ... Read more....»
1216 N CASEY KEY ROAD
OSPREY FL 34229
Residential / Single Family Residence
5 Bed · 6 Bath · 2 Half Baths · 8,050 SqFt · $1,335/SqFt
Days on Market: 311
County: Sarasota
Subdiv/Community Name: Casey Key
Legal Subdivision Name: CASEY KEY
Year built: 1999
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.10
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 and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.