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Looking for a delicious treat in Osprey, Florida? Visit 1 Hot Cookie and Ice Cream located at 1066 Tamiami Trail. This popular spot offers a variety of cookies and ice cream flavors to satisfy your sweet tooth cravings. Open daily from 12:00-21:00, this food and retail establishment is a must-visit for locals and tourists alike. Contact them at +1 941-375-8937 to learn more or place an order.
| Address | Bed / Bath | Listing Price |
|---|---|---|
1235 YACHT HARBOR DRIVE
Relax, you can move right in this one! This Southbay home has been updated beautifully with so many quality and custom features. A complete interior remodel was done in 2016 including all new underground PVC piping. A well thought out floor plan offers plenty of entertaining area including a livin
Living Area:
2698 Sqft.
|
3
Beds,
3
Baths
|
$1,175,000 |
640 CRANE PRAIRIE WAY
Lovely turn-key furnished, 3BR/2BA and a pool half BA, 3 car garage home bordering Oscar Scherer State Park, providing privacy, lake views and peacefulness. The beautiful Stanford 2,534 SqFt model home affords you stunning views out all the wind impact windows. This home features a fabulous great r
Living Area:
2534 Sqft.
|
3
Beds,
3
Baths
|
$765,000 |
102 WINDWARD DRIVE
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large
Living Area:
2134 Sqft.
|
3
Beds,
3
Baths
|
$800,000 |
730 SARABAY ROAD
Premier Intracoastal Estate in Osprey
4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres
A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a
convergence of residential luxury and unparalleled waterfront living. The two-story home sits at
th
Living Area:
6308 Sqft.
|
4
Beds,
6
Baths
|
$5,495,000 |
403 LONGBOW TRAIL
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 Florid
Living Area:
2770 Sqft.
|
4
Beds,
3
Baths
|
$1,197,000 |
180 LOOKOUT POINT DRIVE
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your
Living Area:
3236 Sqft.
|
5
Beds,
4
Baths
|
$2,299,900 |
232 WOODLAND DRIVE
This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey
Living Area:
1325 Sqft.
|
2
Beds,
2
Baths
|
$269,900 |
172 SEA ANCHOR DRIVE
At last- the home you've been looking for! This updated 3-bedroom 3 bath retreat is tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout, saltwater pool, den, in home gym, new tile roof, new AC, hurricane impact windows and doors a
Living Area:
2283 Sqft.
|
3
Beds,
3
Baths
|
$936,000 |
3936 WAYPOINT AVENUE
Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residenc
Living Area:
2323 Sqft.
|
3
Beds,
3
Baths
|
$1,089,000 |
1486 LANDVIEW LANE
Welcome to your Boater's Paradise! This well-maintained South Bay home is your key to enjoy one of the best neighborhoods in the area. This three-bedroom pool home has the perfect layout with the primary bedroom and en suite on one side of the home and the two additional bedrooms on the other. A
Living Area:
1869 Sqft.
|
3
Beds,
2
Baths
|
$995,000 |
315 BAYSHORE DRIVE
Welcome to Bay Acres - a hidden coastal enclave West of the Trail where timeless Florida living meets everyday comfort. Situated on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath single-family pool home offers a spacious and functional split floor plan designed for both priva
Living Area:
2384 Sqft.
|
3
Beds,
3
Baths
|
$659,000 |
700 FAITH AVENUE
One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools i
Living Area:
2474 Sqft.
|
4
Beds,
3
Baths
|
$1,300,000 |
238 LOOKOUT POINT DRIVE
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. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the
Living Area:
2676 Sqft.
|
3
Beds,
3
Baths
|
$895,000 |
18 N CASEY KEY ROAD
Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen,
Living Area:
1977 Sqft.
|
3
Beds,
2
Baths
|
$2,350,000 |
479 S CREEK DRIVE
Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool an
Living Area:
4261 Sqft.
|
5
Beds,
6
Baths
|
$3,200,000 |
510 LATITUDE LANE
Stunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exposure, maintenance-free landscaped lot, this home offers the perfect blend of style, comfort, and functionality.
Interior Highlights-
Architectural Elegance: High tray ceilings, extensive crown molding, and
Living Area:
2298 Sqft.
|
3
Beds,
2
Baths
|
$630,000 |
1036 OAK MEADOW LN
Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built i
Living Area:
2186 Sqft.
|
4
Beds,
2
Baths
|
$585,000 |
225 HARBOR HOUSE DRIVE
Considered one of the finest community owned marinas on Florida’s west coast, Southbay Yacht & Racquet Club is a premier waterfront community featuring a seven acre deep water boat basin and a lifestyle centered around the water. This exceptional 4,560 sq ft residence captures the essence of refin
Living Area:
4546 Sqft.
|
6
Beds,
4
Baths
|
$2,690,000 |
32 BAY AVENUE
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating and waterfront lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb includ
Living Area:
2148 Sqft.
|
2
Beds,
2
Baths
|
$463,000 |
4005 CASEY KEY ROAD
WELCOME TO ONE OF THE FEW BRAND-NEW GULF FRONT HOMES FOR SALE ON THE WEST CENTRAL COAST OF FLORIDA. A rare opportunity, where cutting-edge design meets wide Gulf vistas. Nestled on the prestigious barrier island of Casey Key, this newly constructed Modern Coastal estate by Modesta Homes exemplifies
Living Area:
7977 Sqft.
|
6
Beds,
7
Baths
|
$9,950,000 |
121 N CASEY KEY ROAD
Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key
Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastli
Living Area:
4096 Sqft.
|
4
Beds,
6
Baths
|
$7,100,000 |
312 YACHT HARBOR DRIVE
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
Living Area:
2572 Sqft.
|
4
Beds,
4
Baths
|
$2,299,000 |
219 KEEL WAY
**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including e
Living Area:
2735 Sqft.
|
3
Beds,
3
Baths
|
$1,175,000 |
38 W BAY STREET
Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings wi
Living Area:
2124 Sqft.
|
3
Beds,
2
Baths
|
$899,000 |
742 HARMS DRIVE
Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been succe
Living Area:
1293 Sqft.
|
3
Beds,
2
Baths
|
$545,000 |
123 WINDWARD DRIVE
This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bat
Living Area:
1894 Sqft.
|
3
Beds,
2
Baths
|
$850,000 |
701 EAGLENOOK WAY
A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses.
Conveniently positioned one mile East of US 41, within a mile of
Living Area:
3533 Sqft.
|
4
Beds,
5
Baths
|
$1,075,000 |
508 MEADOW SWEET CIRCLE
PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well
Living Area:
1604 Sqft.
|
2
Beds,
2
Baths
|
$455,000 |
3761 CASEY KEY ROAD
Pre-Construction. To be built. This is your chance to own a newly imagined Gulf-front estate on one of Sarasota’s most exclusive barrier islands. Positioned on 0.43 acres with 107 feet of direct Gulf frontage, this offering presents a 3,489 sq. ft residence designed by the renowned Stofft Cooney A
Living Area:
3489 Sqft.
|
3
Beds,
4
Baths
|
$10,800,000 |
1218 YACHT HARBOR DRIVE
New listing alert in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts,
Living Area:
3297 Sqft.
|
3
Beds,
3
Baths
|
$1,150,000 |
1337 COPPERWOOD DRIVE
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 with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. In
Living Area:
2172 Sqft.
|
3
Beds,
2
Baths
|
$595,000 |
140 N CASEY KEY ROAD
Step into a world where the horizon meets the sea and every sunset paints a masterpiece. This exceptional cedar-sided residence on exclusive Casey Key offers the perfect blend of contemporary elegance and natural beauty along an eight-mile stretch of pristine shoreline. The home features three spaci
Living Area:
2473 Sqft.
|
3
Beds,
4
Baths
|
$2,350,000 |
1602 SOUTHBAY DRIVE
Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle.
As you arrive, the mature tropical landscaping and stately curb appeal immediately set the to
Living Area:
2980 Sqft.
|
4
Beds,
4
Baths
|
$995,000 |
455 N SHORE DRIVE
Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment.
Just minutes from Nokomis Beach, Venice Beach,
Living Area:
1229 Sqft.
|
2
Beds,
2
Baths
|
$549,000 |
614 BAYSHORE DRIVE
New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens
Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water vie
Living Area:
4048 Sqft.
|
3
Beds,
5
Baths
|
$5,500,000 |
144 N CASEY KEY ROAD
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
Living Area:
5397 Sqft.
|
4
Beds,
6
Baths
|
$5,990,000 |
107 COROT DRIVE
Sellers are MOTIVATED, bring all offers. Welcome to 107 Corot Drive, a beautifully renovated pool home tucked away in the highly desirable community of Sorrento East in Nokomis. This spacious 3-bedroom, 2.5-bath home also features a versatile office or den with French doors, perfect for remote work
Living Area:
1786 Sqft.
|
3
Beds,
3
Baths
|
$510,000 |
827 PLACID LAKE DRIVE
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, a
Living Area:
1875 Sqft.
|
2
Beds,
2
Baths
|
$544,700 |
819 SHADOW BAY WAY
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, f
Living Area:
2145 Sqft.
|
4
Beds,
2
Baths
|
$689,000 |
4428 CONCHFISH LANE
Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into th
Living Area:
1861 Sqft.
|
4
Beds,
2
Baths
|
$599,000 |
3203 Casey Key Road
An exquisite Gulf-front property on coveted Casey Key – a rare opportunity in coastal luxury. Experience the unmatched serenity and prestige of Casey Key with this exceptional Gulf-front property offering 48 feet of direct Gulf frontage on one of Florida’s most exclusive barrier islands. Nestled
Living Area:
1467 Sqft.
|
3
Beds,
4
Baths
|
$1,450,000 |
3203 Casey Key RD
An exquisite Gulf-front property on coveted Casey Key – a rare opportunity in coastal luxury. Experience the unmatched serenity and prestige of Casey Key with this exceptional Gulf-front property offering 48 feet of direct Gulf frontage on one of Florida’s most exclusive barrier islands. Nestled
Living Area:
1467 Sqft.
|
3
Beds,
4
Baths
|
$1,450,000 |
1363 NEW FOREST LANE
Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with ple
Living Area:
1738 Sqft.
|
2
Beds,
2
Baths
|
$499,000 |
3201 CASEY KEY ROAD
Gulf-front serenity on Casey Key. On the desirable shores of Casey Key, this quintessential beachfront retreat, Osmyrrah, is a sanctuary of tranquility, designed for relaxed, organic living with an intimate connection to the sea. With private, pristine beachfront and panoramic Gulf views, you’ll b
Living Area:
3273 Sqft.
|
4
Beds,
4
Baths
|
$3,995,000 |
110 PINE AVENUE
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
Living Area:
2058 Sqft.
|
3
Beds,
2
Baths
|
$699,000 |
820 PLACID LAKE DRIVE
Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool
Living Area:
3938 Sqft.
|
5
Beds,
4
Baths
|
$1,095,000 |
3858 CASEY KEY
Casey Key is the ultimate island retreat, offering the perfect escape for those seeking a serene, barefoot lifestyle. This secluded hideaway presents both beach and boating waterfront with a refined yet tropical atmosphere. The home has been fully updated with new flooring and brand-new furniture, e
Living Area:
1729 Sqft.
|
3
Beds,
2
Baths
|
$2,595,000 |
4024 CASEY KEY ROAD
A RARE CASEY KEY OPPORTUNITY — Discover a 4,300+ sq. ft. STORM-RESISTANT waterfront residence that blends privacy, craftsmanship, and breathtaking bay views on one of Florida’s most exclusive barrier islands. This move-in ready estate sits on the serene shores of Little Sarasota Bay, offering a
Living Area:
4347 Sqft.
|
4
Beds,
4
Baths
|
$2,150,000 |