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758 Sarabay Road Unit 5, Osprey
$598,000
2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code
Beautiful views of Little Sarasota Bay and a peaceful waterfront setting are just the beginning of what makes this updated villa in Heron Bay Club so appealing. Tucked along the shores of Little Sarasota Bay, this intimate waterfront community consists of just 25 single-story villas situated on approximately 10 acres across from the northern end of Casey Key. Surrounded by natural beauty and offering a quiet, private setting, Heron Bay Club captures the charm of Old Florida without sacrificing convenience. The villa enjoys beautiful views of the bay, along with the community pond and its decorative fountain, creating a picturesque backdrop. Interior improvements include updated electrical outlets and switches, a tankless water heater, newer appliances, and an A/C system replaced in 2021. A private courtyard offers additional outdoor living space, while the attached two-car garage is a particularly desirable feature not found in every residence within the community. The spacious attic with high ceilings provides even more storage, a welcome bonus in condominium living. For those who enjoy spending time on the water, Heron Bay Club has plenty to offer. Residents enjoy a heated swimming pool, tennis courts, and a fishing pier. Boating enthusiasts will especially appreciate the availability of boat dockage at no additional fee, providing convenient access to the Intracoastal Waterway and Gulf. Whether boating, fishing, or simply watching the dolphins, manatees, and coastal birds that frequent the area, the waterfront lifestyle is an everyday part of life here. The community's western exposure also provides a beautiful setting to enjoy sunsets over Little Sarasota Bay. Another standout feature of Heron Bay Club is just how much is included in the association fee. In addition to maintaining the beautifully landscaped grounds and community amenities, the fee covers water, high-speed internet, cable television, pest control, building flood insurance, exterior building maintenance and painting, roof maintenance and repairs, trash collection, and more. With so many services and expenses already included, residents can enjoy the benefits of a low-maintenance lifestyle with fewer individual bills and responsibilities. Unlike traditional multistory condominium buildings, Heron Bay Club's single-story villas offer the privacy and convenience of having no elevators or neighbors overhead. The community's small size and private courtyards create a more residential feel than what is typically found in larger waterfront condominium developments. Despite its peaceful setting, Heron Bay Club is conveniently located near beautiful Gulf beaches, shopping, restaurants, and the arts and cultural attractions of Sarasota. With its combination of water views, boating access, extensive association benefits, and intimate community atmosphere, this home offers a distinctive opportunity to enjoy Florida's Gulf Coast lifestyle.

758 Sarabay Road Unit 5, Osprey
232 Hidden Bay Drive Unit 303, Osprey
$569,000
2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code
Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths, a spacious den and a three-car garage. The lanai’s exterior sliders open to an all-season, tiled living area where you can enjoy birdwatching and wildlife in the mangroves, observe passing boats, feel gentle bay breezes and take in spectacular sunsets. The wonderfully efficient kitchen features Corian countertops, a breakfast bar with seating for four, new (2025) LG stainless steel appliances and abundant pantry storage within newly outfitted cabinetry, complete with pullout drawers in the kitchen and baths. This beautifully appointed home showcases Acacia engineered flooring, high ceilings, a generous laundry room with newer GE appliances, a sink, tile flooring and ample storage, plus a den or office off the breakfast area. This condominium features a rare three-car garage which includes a private single garage, allowing this space to be used as art studio workshop, or the ever-elusive onsite storage unit along with a separate and spacious two-car garage on the first level. A new roof and updated elevator motor were added in 2025, along with completed Milestone and Reserve studies. Many of the attractive furnishings are available under a separate bill of sale. This exceptional gated waterfront community features a 1,500-foot elevated wooden boardwalk winding through lush landscaping and palm-lined grounds, leading to a private bay front fishing pier. Residents enjoy a renovated clubhouse offering a full kitchen, with granite bar and graciously appointed social area which can be used for private events. Owners also enjoy a fully stocked library, a professional fitness center, and an entertainment and media area. Outside the clubhouse, there is a heated pool, hot tub and tiki hut for additional social gatherings. Hidden Bay is conveniently near restaurants, shopping, Legacy Trail and Nokomis Beach. Osprey is a lovely area between Sarasota and Venice featuring old Florida vibes, peaceful surroundings, and an easy, quiet, lifestyle. Seller willing to lease back.

232 Hidden Bay Drive Unit 303, Osprey
14041 Bellagio Way Unit 315, Osprey
$640,000
3 Beds ⋅ 2 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
There is something extraordinary about living on the water, where passing sailboats, coastal breezes, and the beauty of the marina become part of everyday life. Welcome to Osprey Harbor Village, an intimate waterfront community perfectly positioned between Sarasota and Venice, where timeless elegance meets the relaxed sophistication of Southwest Florida living. From the moment you enter, the welcoming foyer introduces a thoughtfully designed residence that balances comfort, elegance, and effortless entertaining. The spacious kitchen features rich upgraded wood cabinetry, granite countertops, stainless steel appliances, and a generous breakfast bar where family and friends naturally gather. An inviting dining area transitions into the comfortable living room, with access to the expansive terrace that truly sets this home apart. Whether entertaining guests, enjoying a quiet evening, or simply watching the activity along the waterfront, this outdoor living space is destined to become one of your favorite places. The generously sized primary suite offers a peaceful retreat with a spacious walk-in closet and an ensuite bath featuring dual vanities, a soaking tub, separate shower, and private water closet. Two additional bedrooms provide wonderful flexibility for visiting family and friends, a home office, or whatever suits your lifestyle. Beyond the residence, Osprey Harbor Village offers an exceptional waterfront experience. This boutique community of just 54 condominiums showcases distinctive Italian-inspired architecture and was constructed in 2006 to hurricane building standards. Boating enthusiasts will appreciate the marina setting and approximately 7-foot draft channel, providing access to the beautiful waterways that make Florida's Gulf Coast a boating paradise. Whether you enjoy sailing, cruising, fishing, kayaking, or simply admiring the boats from your terrace, life here revolves around the water. The community amenities create an atmosphere that feels more like a private waterfront resort. Enjoy a newly renovated, fully equipped fitness center, sparkling community pool, poolside grilling area, relaxing spa, sauna, steam room, fishing dock, and kayak launch. Spend your afternoons poolside, take a peaceful paddle along the waterways, or gather with friends after a day of exploring the coast. Additional conveniences include two assigned garage parking spaces, onsite management, and a pet-friendly environment welcoming up to two large dogs. And the location? It's one of the best parts. Imagine being able to stroll to waterfront dining at Deep Lagoon Seafood & Oyster House or the beloved Casey Key Fish House, enjoy the casual atmosphere of a nearby tiki bar, or explore the waterfront park just across the street. The beautiful beaches of Casey Key are only a short drive away, while Publix, shopping, restaurants, medical facilities, and the endless attractions of Sarasota and Venice are all conveniently nearby. From boating adventures and beach days to waterfront dining and peaceful evenings at home, the possibilities are endless. What makes Osprey Harbor Village truly special isn't simply the architecture, the amenities, or even the spectacular marina setting. It's the lifestyle that comes with it. Spend more time outdoors, entertain the people you love, and enjoy the beauty of coastal living in a community that feels both exclusive and welcoming. Discover the waterfront lifestyle waiting for you at Osprey Harbor Village today!

14041 Bellagio Way Unit 315, Osprey
570 Blackburn Point Road Unit Siesta 25, Osprey
$149,900
Dry Slips At Bellagio Village SubDv. ⋅ 34229 Zip Code
This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 10.5' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks, fillet tables, outside patio area, fresh deli, drinks, ice, snacks, live and frozen bait. Enjoy your day out on the water and when you return, the staff will flush your engines, wash around the waterline and put your boat to bed, leaving you the freedom to just enjoy boating.

570 Blackburn Point Road Unit Siesta 25, Osprey
168 Coastal Hammock Court, Osprey
$1,900,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

168 Coastal Hammock Court, Osprey
1216 N Casey Key Road, Osprey
$9,750,000
5 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code
At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

1216 N Casey Key Road, Osprey
260 Hidden Bay Drive Unit 402, Osprey
$775,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy breathtaking sunsets from your private screened-in balcony as you look out across the bay to the barrier island of Casey Key. Inside the unit, you'll find a spacious living room and dining room featuring an open floor plan. The gourmet kitchen offers KitchenAid stainless steel appliances, quartz countertops, white shaker-style cabinetry, counter seating and plenty of storage cabinets. The primary bedroom is expansive with large walk-in closets, closet organization system and direct access to the outside balcony. Both guest bedrooms have dual purpose, as they both have built-in Murphy beds, desk workstations, plantation shutters and walk-in closets. If you're looking for a condominium with extra space for a den/office/sewing room/craft room or TV media room, this is the one that offers it all. More great features are impact-resistant windows and doors, a large laundry room with built-in cabinetry, a full-size washer and dryer and utility sink. One assigned parking space with a large storage unit with a roll-down door for all your extra gear. Some of the amenities include a new fishing pier, lit pickleball courts, kayaking and kayake racks for storage, clubhouse, swimming pool, spa and tiki hut with grilling barbeque stations. The location is walkable to many restaurants, shopping and the post office. Bike the Legacy Trail or head to the beach that's just a few miles away. There's so much to do just minutes away.

260 Hidden Bay Drive Unit 402, Osprey
570 Blackburn Point Road Unit 36, Osprey
$99,500
Osprey Avenue Sub SubDv. ⋅ 34229 Zip Code
This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 9' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks, fillet tables, outside patio area, fresh deli, drinks, ice, snacks, live and frozen bait. Enjoy your day out on the water and when you return, the staff will flush your engines, wash around the waterline and put your boat to bed, leaving you the freedom to just enjoy boating.

570 Blackburn Point Road Unit 36, Osprey
780 Sarabay Road Unit 16, Osprey
$425,000
2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code
Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with maintenance-free grounds and an all-inclusive HOA that covers insurance, roof, exterior maintenance, landscaping, roads, pool and tennis facilities, docks/boat slips, cable TV, high-speed internet, water, trash and sewer. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and new countertop, The vaulted-ceiling living room offers tranquil lake views overlooking the bay, with many evenings capped by stunning sunsets over the Bay. STORAGE! in addition to the garage there is an interior attic! Outside, a 587 sqft courtyard with a hot tub invites outdoor relaxation and entertaining and expands the indoor-outdoor living space to 2,161 sqft Community amenities include a heated bayside swimming pool, tennis court, a fishing pier, kayak launch, and dockage for 10 boats—complete with electric and water—available to residents at NO COST. This is a very private location. Located directly on Little Sarasota Bay with no fixed bridges near MIDNIGHT PASS, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Nokomis beach is only a few miles away. Enjoy waterfront dinning at Casey Key Fish House, The Point and Deep Lagoon Oyster House. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.

780 Sarabay Road Unit 16, Osprey
14021 Bellagio Way Unit 404, Osprey
$999,900
3 Beds ⋅ 3 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. Arrive in effortless luxury with an elevator that opens directly into this beautifully appointed condo, creating an exceptional sense of privacy and exclusivity. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!

14021 Bellagio Way Unit 404, Osprey
242 Hidden Bay Drive Unit 602, Osprey
$700,000
2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code
PENTHOUSE WATERFRONT LIVING WITH STUNNING BAY VIEWS! This exceptional sixth-floor residence at Hidden Bay offers expansive views across Little Sarasota Bay and the Intracoastal Waterway, with the Gulf beyond Casey Key in the distance. From the moment you enter, soaring ceilings, tall interior doors, abundant natural light, and water views throughout the main living areas create a bright and inviting sense of space. The spacious great room seamlessly combines living and dining areas and opens to an enclosed waterfront sunroom—an ideal spot to relax, entertain, or simply enjoy breathtaking sunsets over the bay. The kitchen features ALL NEW APPLIANCES, including a side-by-side refrigerator/freezer, microwave, range/oven, and dishwasher, along with a counter-height breakfast bar, pantry storage, and adjoining dining nook. A separate den provides versatile space for a home office, media room, or guest area. The waterfront primary suite is designed to take full advantage of the spectacular views, with a wall of windows and impact sliders opening to the adjacent sunroom. The luxurious en-suite bath features dual vanities, a soaking tub, walk-in shower, water closet, and dedicated makeup vanity, while multiple closets provide generous storage. The second bedroom offers an adjoining bath and walk-in closet. Luxury vinyl flooring extends throughout the bedrooms and den, and a NEW WASHER AND DRYER are conveniently located inside the residence. A private, fully enclosed TWO-CAR GARAGE provides secure parking and additional storage. Furnishings are included, allowing the residence to convey turnkey as presented, or they can be removed according to the buyer’s preference. Hidden Bay is a gated waterfront community offering an impressive array of amenities, including a clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, kayak storage and launch, and a scenic mangrove boardwalk leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay places you conveniently between Sarasota and Venice, with easy access to Gulf beaches, the Legacy Trail, shopping, dining, and the many attractions of Florida’s Gulf Coast. A rare opportunity to enjoy penthouse-level waterfront living, spectacular sunsets, resort-style amenities, and the convenience of a private two-car garage—all in one exceptional Osprey residence.

242 Hidden Bay Drive Unit 602, Osprey
570 Blackburn Point Road Unit 13, Osprey
$109,000
Dry Slips At Bellagio Village SubDv. ⋅ 34229 Zip Code
The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is also an onsite boat detailing company, independent mechanic, as well as boat transporter. The marina is centrally located between Sarasota and Venice on Little Sarasota Bay. It is just minutes from Midnight Pass...the highly anticipated new opening project being reviewed by Sarasota County. Open seven days a week

570 Blackburn Point Road Unit 13, Osprey

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