Osprey/Nokomis Homes with Sailboat Water Water Frontage

Osprey/Nokomis Homes with Sailboat Water Water Frontage

Welcome to Osprey and Nokomis, two enchanting communities nestled in the heart of Sarasota County, Florida. Known for their stunning natural beauty and laid-back coastal lifestyle, these charming towns offer a unique blend of tranquility and adventure, making them a perfect destination for homebuyers seeking a slice of paradise.

Osprey, with its lush landscapes and rich history, boasts an array of parks, nature trails, and waterfront access that beckon outdoor enthusiasts. Meanwhile, Nokomis, famous for its pristine beaches and warm Gulf waters, invites residents to enjoy sun-soaked days and breathtaking sunsets. Together, these communities provide a vibrant atmosphere that combines the best of both worlds—relaxation and recreation.

For those dreaming of a home with sailboat water frontage, Osprey and Nokomis are ideal. Imagine stepping out of your back door onto your private dock, ready to set sail into the sparkling waters of the Gulf of Mexico. Properties in this area offer not just stunning views but also direct access to some of the best sailing, fishing, and boating experiences Florida has to offer. Whether you're an avid sailor or simply love the idea of living on the water, homes with sailboat water frontage in Osprey and Nokomis are truly a dream come true.

With a welcoming community, top-notch amenities, and a lifestyle that celebrates the great outdoors, Osprey and Nokomis are more than just places to live—they're places to thrive. Discover your perfect waterfront haven and embrace the serene coastal life in this stunning corner of Florida.

Newest Osprey/Nokomis Homes with Sailboat Water Water Frontage

$825,000
3 Beds ⋅ 2 Baths ⋅ Inlets SubDv. ⋅ 34275 Zip Code
Welcome to The Inlets, a highly sought-after waterfront community located just one mile from Nokomis Beach, where boating and golf cart living are part of the daily lifestyle. This beautifully maintained canal-front pool home offers a desirable south-facing backyard, private dock with boat lift, and exceptional updates, including a new roof and pool cage (2025) and a new electrical panel (2026). The popular Catalina floor plan features high ceilings, an open-concept design, tile flooring throughout the main living areas, granite countertops, stainless steel appliances, and a split-bedroom layout for added privacy. The spacious primary suite includes dual walk-in closets, an en-suite bath with dual vanities and a walk-in shower, garden tub, and sliding glass doors opening to the covered lanai and screened pool. The third bedroom has been thoughtfully converted into a custom office with built-in shelving, storage, and a corner desk, providing an ideal work-at-home space. Accordion shutters protect the oversized lanai and exterior, while Flood Zone X-500 offers added peace of mind. Monthly HOA fees include cable TV, high-speed internet, lawn maintenance, exterior insurance, and access to outstanding resort-style amenities, including a heated pool and spa, fitness center, tennis and pickleball courts, clubhouse, and a full calendar of social activities. Pet-friendly with two pets allowed under 40 pounds, this exceptional home is also available turnkey furnished with some exceptions, making it the perfect opportunity to begin enjoying Florida's coveted waterfront lifestyle.

103 Inlets Boulevard Unit 103, Nokomis
$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
$2,699,000
6 Beds ⋅ 5 Baths ⋅ Casey Cove SubDv. ⋅ 34275 Zip Code
This home comes with a deeded private beach access. Welcome to your own private slice of paradise, tucked at the end of a quiet cul-de-sac where every day feels like a vacation. This spectacular 6-bedroom waterfront retreat sits gracefully along the shimmering Intracoastal Waterway, offering front-row seats to breathtaking sunrises and endless water views from nearly every room. Wake up to golden light pouring through expansive windows, sip your morning coffee on the your private deck, and watch the boats glide by as dolphins occasionally make a surprise appearance. Outside, the fun continues in your personal resort-style oasis—featuring a sparkling swimming pool, soothing spa, and a wide-open deck made for lounging, entertaining, and unforgettable sunset gatherings. For boating enthusiasts, the possibilities are endless. Design your dream dock and set sail anytime with direct access to the Gulf of America via the nearby Venice Jetty—no fixed bridges, no limits, just open water adventures waiting for you. Inside, the home blends comfort and style with a stunning custom kitchen equipped with modern appliances, perfect for preparing fresh coastal meals after a day on the water or at the beach. And speaking of the beach—this home offers something truly special. With deeded private beach access just steps away, your toes can be in the sand in seconds. No car, no hassle—just cross the street and enjoy the gentle waves, salty breeze, and picture-perfect sunsets that make every evening feel magical. Located just one mile from Nokomis Beach, this incredible property is more than a home—it’s a lifestyle. Whether you're hosting, relaxing, or exploring, this waterfront escape delivers the ultimate blend of luxury, fun, and coastal charm.

919 Key Way, Nokomis
$1,650,000
0000 - Not Part Of A Subdivision SubDv. ⋅ 34275 Zip Code
Build your dream waterfront home on this exceptional homesite featuring deep sailboat water, no bridges to the Gulf, and breathtaking panoramic views of Roberts Bay. With direct access to the Intracoastal Waterway and the Gulf, this rare property is a boater's paradise. Ideally situated just minutes from both Venice Beach and Nokomis Beach, as well as the shopping, dining, and charm of historic Venice Island, this premier location provides the very best of Southwest Florida's coveted coastal lifestyle. Spend your days on the water boating, fishing, kayaking, paddleboarding, or simply relaxing while enjoying spectacular sunset views from your own backyard. Whether you envision a luxurious waterfront retreat or a custom-designed coastal estate, available floor plans and design options provide the perfect starting point to bring your vision to life. This is a your opportunity to own one of the area's most desirable waterfront properties and create the Florida Gulf Coast home you've always imagined.

325 Sunrise Drive, Nokomis
$25,000
Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code
Rare opportunity to own a highly desirable rackominium at Gulf Harbor Marina, ideally situated on the Intracoastal Waterway in Nokomis with quick Gulf access through the Venice Inlet. This storage rack measures approximately 8.8' W x 8' H x 25' L, offering a secure, covered home for your boat while protecting it from Florida's intense sun and harsh weather. Stop trailering your boat and start enjoying the convenience of professional dry storage. Eliminate the need for a truck and trailer while keeping your vessel safely housed in a covered facility. It's the perfect solution for homeowners living outside a flood zone who want to avoid the expense of storing a boat at home. Ownership includes unlimited put-ins and pull-outs seven days a week, making last-minute boating adventures effortless. After every outing, the marina staff will flush your engine and rinse the bottom of your boat before returning it to your rack. Owners also enjoy discounted fuel at the on-site fuel dock. Gulf Harbor Marina is professionally maintained and offers a certified forklift operator, on-site service department, dock store with bait and ice, restrooms, security cameras, and recently completed improvements including new decking and all-new seawalls. Whether your passion is offshore fishing, cruising the Intracoastal, or relaxing on sunset cruises, you'll be on the water within minutes. Better yet, you'll return to two popular waterfront restaurants located right next door—Pop's Sunset Grill and Pelican Alley—perfect for a meal or refreshing drink after a day on the water. From this exceptional location, cruise to favorite boating destinations including Snake Island, Midnight Pass, Nokomo's Sunset Hut, Dockside Waterfront Grill, Crow's Nest Restaurant & Marina, Waterfrontoo, Casey Key Fish House, Evie's at Spanish Point, Siesta Key, The Lighthouse Grill, Rum Bay Restaurant, White Elephant Pub, and countless hidden beaches, waterfront tiki bars, and dockside restaurants that make Southwest Florida boating so unforgettable. If you've been looking for the ultimate combination of convenience, protection, and immediate access to some of Florida's best boating waters, this is an opportunity you won't want to miss.

100 Circuit Road Unit N12, Nokomis
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally Elegant Bath. CoreTec Vinyl Flooring throughout (except guest bedroom). Enjoy the serene and natural surroundings from your elevated, sprawling and screened balcony which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Private covered parking and storage are located on the ground level within the building. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer! **RECENTLY COMPLETED PROJECTS INCLUDE: ASPHALT PAVING, IRRIGATION, WALKWAYS, WALKWAY LIGHTING, LIGHTING at TENNIS AND PICKLEBALL COURTS, etc.

7204 Jessie Harbor Drive Unit 7204, Osprey
$5,495,000
3 Beds ⋅ 3 Baths ⋅ 34275 Zip Code
Positioned on 1.9 private waterfront acres with approximately 200 feet of bay frontage, this exceptional estate offers a rare combination of immediate waterfront enjoyment and long-term flexibility. With multiple docks and direct access to Sarasota Bay, the property is ideally suited for those seeking an authentic waterfront lifestyle defined by boating, fishing, recreation and effortless access to the Gulf Coast's most desirable destinations. Spanning approximately 2,960 square feet under air, the residence blends rich architectural detailing with panoramic water and nature views throughout. Wood-trimmed windows, doors and millwork, tray ceilings, recessed lighting, large-format tile flooring and extensive custom cabinetry create a warm yet elevated atmosphere. The open-concept layout is anchored by a spacious great room featuring a built-in gas fireplace, custom entertainment wall and expansive sliding glass doors that create seamless indoor-outdoor flow. The kitchen is designed for both entertaining and everyday living with a Viking dual-oven gas range with integrated griddle and char broiler, Sub-Zero refrigerator, Bosch dishwasher, custom wood cabinetry, decorative copper lighting, integrated wine storage, center island with prep sink and a waterfront breakfast nook with terrace access. The primary suite serves as a private retreat with French doors to outdoor living areas, water and pool views, a custom walk-in closet and a spa-inspired bath featuring a Jacuzzi tub, dual vanities and an oversized walk-in shower. Additional spaces include a private office, guest suite and flexible bonus/game room complete with projector screen, surround sound system, wet bar, beverage refrigerator and French doors opening to the outdoor areas. Outdoor living is thoughtfully designed with an upper-level covered waterfront terrace, raised spa, screen-enclosed resort-style pool terrace, multiple lounge areas and tropical landscaping overlooking the water. For boating enthusiasts, the property features a new private composite dock with a 12,000-pound Deco boat lift, water and electric service, fish cleaning station and deep-water access and a second dock. Completing the property is an attached 2-car garage and a rare detached air-conditioned garage complex with capacity for up to 7 vehicles, workshop space, office area and extensive storage for boats, golf carts, trailers and recreational equipment. The property presents a potential opportunity for future division into two distinct waterfront homesites, each benefiting from approximately 100 feet of water-frontage. The northern parcel would encompass the existing residence and detached garage complex, while the southern parcel offers the potential for a premier bayfront homesite. Beyond its exceptional development potential, the estate delivers deep-water boating access, expansive garage capacity and thoughtfully designed indoor-outdoor living. The property is just moments from waterfront dining, marinas and beaches that define the Gulf Coast lifestyle. Nokomis Beach, Venice Island, Legacy Trail, Casey Key, Oscar Scherer State Park and downtown Venice are all nearby, while quick access to Sarasota, the barrier islands and Interstate 75 allow for effortless travel throughout the region. Combining acreage, waterfrontage, boating infrastructure and exceptional garage capacity, this is a rare opportunity to experience the best of Florida waterfront living.

612 Laurel Road W, Nokomis
$1,900,000
3 Beds ⋅ 2 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
Welcome to 216 Sunrise Dr in Nokomis, FL! A one-of-a-kind waterfront estate designed for the discerning luxury buyer and true automotive enthusiast. Perfectly positioned on Roberts Bay with no bridges to the Bay or Gulf, this extraordinary residence combines coastal elegance, cutting-edge upgrades, and unmatched garage capacity in a private tropical setting. Built for both beauty and resilience, the home features over $80,000 in CAT5-rated PGT hurricane-impact windows and doors, new HVAC systems raised for protection, all-new PVC re-piping completed in 2024/2025, updated electrical throughout, and a hybrid septic system replaced approximately three years ago. The roof has been professionally re-screwed and resealed, while the entire home has been enhanced with sprayed foam insulation across all attic spaces for superior efficiency. Inside, warm luxury details define the living spaces, including stunning wood accent walls, remodeled bathrooms, custom kitchen features, a spacious primary bath shower, Glor and More blinds, tankless instant hot water system (2025), ventless remote-controlled fireplace, and over 11 closets plus a walk-up loft attic with generous walkable space for exceptional storage, hobbies or future customization. Historic character meets modern refinement with a bundle of aged red oak flooring included. Outside, the grounds rival a private resort with over $200,000 invested in pavers, extensive lighting, and professionally designed landscaping featuring approximately $70,000 in nighttime illumination. Additional exterior highlights include a new fence, Mexican black river rock accents, irrigation systems utilizing both well and county water, underground gutter systems, a fountain, fire pit with updated tanks and hoses, outdoor utility sink, grill area, and sandy-bottom waterfront access. For boating enthusiasts, the property offers one of the area’s largest mooring dock setups, a 10,000-lb boat lift, two brand-new multi-level jet ski lifts, remote-controlled lifts, underwater survey completed, dock lighting, and regularly maintained mangroves. Enjoy direct boating access with no bridges to the Bay or Gulf. The ultimate car lover’s paradise, this estate features up to 6-car garage capacity with taller 4-car garage bays, exotic-car-compatible wide lifts, side-mount garage doors, silent openers, epoxy flooring, mini-split climate systems, block garage construction, and foam insulation throughout. Every detail was designed with collectors and enthusiasts in mind. Additional features include: New interior and exterior Rain Refresh paint, Brand-new irrigation pump, Hurricane-rated upgrades throughout, Utility well servicing property irrigation, Block and Hardie board exterior construction, Raised back door elevation approximately 3.5 feet above sea level, Termite tenting completed approximately 5 years ago, Three septic tanks located on right side yard, Updated shell landscaping and hardscape finishes. Attention to detail was not missed, every upgrade was done with thought and cost was not spared! 216 Sunrise Drive is a rare opportunity to own an extensively upgraded waterfront retreat where luxury living, boating lifestyle, and exotic car storage converge into one exceptional property. Schedule your private showing today!

216 Sunrise Drive, Nokomis
$4,795,000
5 Beds ⋅ 4 Baths ⋅ Sorrento East SubDv. ⋅ 34275 Zip Code
Tucked away at the end of a quiet road on a breathtakingly private one-acre homesite, this extraordinary luxury gated estate overlooks the serene waters of South Creek with the untouched natural beauty of Oscar Scherer State Park creating an incomparable backdrop. Completely reimagined with a sophisticated contemporary aesthetic, this custom-built residence blends timeless architecture with high-end designer finishes and luxurious modern upgrades throughout. From the moment you arrive, the home makes a striking impression with its expansive front porch, lush new landscaping, updated driveway and beautiful natural surroundings. Inside, every space has been thoughtfully transformed with premium materials, stylish finishes, and exceptional attention to detail. The result is a home that feels luxurious and inviting with a chic contemporary style rarely found. Featuring five bedrooms and 3.5 baths, the expansive floor plan is designed for both elegant entertaining and comfortable everyday living. Upon entering, stunning views of South Creek immediately draw your attention through the open living spaces and out toward the resort-style outdoor setting. The completely redesigned gourmet kitchen is the centerpiece of the home, showcasing KitchenAid® professional appliances, custom cabinetry, designer lighting, and luxurious finishes throughout. The spacious family room with a built-in electric fireplace flows seamlessly from the kitchen, while the formal dining room, butler’s galley and large walk-in pantry create the perfect setting for upscale gatherings and entertaining. Additional bonus spaces include a large media/game room with flexibility for a home theater, fitness space, billiards room or lounge area. Throughout the home, every detail has been elevated, including new flooring, custom wall accents, designer paint selections, premium fixtures, sophisticated lighting and beautifully renovated baths and living spaces. Anderson windows further enhance the quality and craftsmanship found throughout the residence. Upstairs, two oversized guest bedrooms feature walk-in closets connected by a Jack-and-Jill bath, while built-in desk spaces create ideal work-from-home or study area flexibility. Outdoor living is equally spectacular and has been totally reimagined. The new covered and screened lanai with outdoor kitchen overlooks the newly enhanced pool and spa area featuring a brand-new picture-frame pool cage and elegant paver deck. Beyond the pool, a dock extends toward the peaceful waters of South Creek, where panoramic natural views and complete privacy create a truly breathtaking setting. The dock and creek can accommodate a boat up to approximately 24 feet with direct access to the Intracoastal Waterway and beyond, offering an exceptional opportunity to enjoy boating, waterfront dining, and the waterfront lifestyle directly from your backyard. Completing the property is an oversized three-car garage with abundant space for vehicles and recreational storage along with an additional shed for tools and equipment. A one-year home warranty is included. The home features 69 solar panels that provide electrical service to the entire home and heated saltwater pool. This system is not financed. Private, stylish, luxurious and surrounded by nature, this exceptional waterfront estate offers a rare opportunity to own a fully transformed retreat in one of Nokomis’ scenic and secluded locations.

4678 Silent Creek Way, Nokomis
$549,000
Mobile City SubDv. ⋅ 34275 Zip Code
Build your waterfront dream home on this oversized 17,000-square-foot cleared, filled and ready homesite with spectacular long sunset views of Shakett Creek Bay and Legacy Trail Bicycle Bridge. A concrete seawall in place on both sides of the property, with a new 10,000-pound boat lift. Electric and water meters are at the property. The lot is a 15-minute boat ride to the gulf with a bridge clearance of 12 to 13 feet, allowing for larger boats. The bike trail, highly rated Pine View School, new Sarasota Memorial Hospital, Nokomis Beach and downtown Venice and shopping are all a short distance. Don’t miss this reasonably priced waterfront property. Owner financing is available.

223 Ravenna Street, Nokomis
$3,295,000
3 Beds ⋅ 5 Baths ⋅ Sorrento Shores SubDv. ⋅ 34229 Zip Code
**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Originally built in 1965, then Demolished and Re-Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level entails an additional nonconforming bedroom, bathroom and recreation room with access to outdoor patio. 4-Car Garage plus extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.

135 Tina Island Drive, Osprey
$725,000
2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code
Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.

5100 Jessie Harbor Drive Unit 304, Osprey
Start Your Search