Osprey/Nokomis Homes with Sailboat Water Water Frontage

3 Beds ⋅ 5 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code

"Selling Sunset Dr” FURNISHED AND TURNKEY. Positioned 15 feet above sea level and built to 2019 hurricane standards with solid block construction and a clay tile roof, this coastal Mediterranean estate on Dona Bay offers a rare combination of newer construction, direct no-fixed-bridge access to the Gulf via Venice Jetty (5 minutes to the jetty), and a garage built for serious car collectors and RV enthusiasts. The 6-car garage with 50-amp RV hookup and parking for 10 vehicles, make this home one of the few on the market at this scale. Inside, three ensuite bedrooms and a private office are finished with solid custom cabinetry with granite and Cambria quartz counters, and engineered hardwood floors. You will appreciate the newly remodeled culinarian inspired kitchen with upmarket appliances, central vac, and whole-house sound system. A Generac 22kW generator and an elevator shaft prepped for future installation add further peace of mind and flexibility. Step outside to a raised infinity-edge pool and spa, two outdoor kitchens, three fire pits, a golf putting green, a tool shed and an extended entertainment lanai with an upper sun deck, frame exquisite water views. A private 100-ft dock with a 16,000 lb lift that includes approval for a second lift.

107 Sunset Drive, Nokomis

$37,000

Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code

This premium marina dock slip offers the ultimate combination of convenience, top-tier service, and immediate deep-water access. Slip S-7 is 40L x 10W X 8.5H, and can suit a vessel that is 39L X 9W X 7.5H and is located on the top middle rack in the South building. Gulf Harbor Marina is situated in a prime location just 10 minutes from the Venice Jetty and the I-75 corridor, this full-service marina boasts No Fixed Bridges to the Gulf pathway, making it a boater's dream. Environmental excellence and peace of mind come standard, as the facility proudly holds both Clean Marina and Clean Boatyard Designations. Property management is highly cost-effective with low monthly administrative charges, while the facility stays open 7 days a week to serve you. Your boating lifestyle is fully supported by an impressive suite of on-site amenities and professional care. Unmatched Convenience: Enjoy unlimited splashes a month powered by large capacity fork trucks, alongside dedicated boat wash racks, a fish station, and a flush service. Fuel & Supplies: Access discounted fuel sales for owners and tenants, with ice, live shrimp, and frozen bait available right at the fuel dock. There are several covered self service bays to work on your vessel with water and electric provided. Attached to the marina is a service shop if you choose to hire a technician to work on your boat as well as a parts supply shop to prick up any boat or motor parts you might need. Gulf Harbor Marina is located adjacent to two waterfront restaurants and just moments from a county park, public beach, and a public boat ramp. Experience stress-free boating backed by award-winning service in a location that puts the open ocean minutes from your slip.

100 Circuit Road Unit S-7, Nokomis

$599,000

2 Beds ⋅ 2 Baths ⋅ Nokomis Sub SubDv. ⋅ 34275 Zip Code

Virtually Staged. Your own private dock, boat lift and Gulf access right in your backyard. Built in 2018, this Key West-style home brings together everything you want in Florida living: newer construction, a peaceful waterfront setting and the freedom to be on the water whenever you want. A private 25-foot dock and 7,000-pound boat lift make it easy to enjoy boating, jet skis, kayaks or paddleboards right from home. From Curry Creek, cruise into Roberts Bay and out to the Gulf of Mexico through the Venice Jetties. Native mangroves create a peaceful and private Old Florida setting along the water. With 1,952 square feet of living space, the home feels open and comfortable throughout. The open floor plan is perfect for relaxed Florida living and entertaining. The kitchen features granite countertops, KitchenAid stainless steel appliances, a breakfast bar and plenty of cabinetry, all open to the great room. Large sliders open fully to the covered lanai, bringing the indoor and outdoor living spaces together. The generous 14' x 11' den gives the floor plan the flexibility of a three-bedroom home, with plenty of room for guests, a home office or additional living space. The split floor plan offers privacy between the primary and guest bedrooms. The primary suite features a large bath with dual sinks, a soaking tub and separate shower, while the guest bedroom offers a comfortable and private space for family and friends. Quality construction sets this home apart, with concrete-block construction, fiber-cement siding, PGT hurricane-impact windows, a metal roof, reinforced two-car garage door and extensive foam insulation throughout the attic and walls. The home is elevated and has never experienced flooding. Located in Cottages on Curry Creek, a gated enclave of just 12 Key West-style homes, lawn care and irrigation are included for easy, maintenance-free living. Whether you're looking for a full-time residence, second home or Florida getaway, this home makes it easy to enjoy the Florida lifestyle. Located in a small gated community, the Legacy Trail is less than half a mile away, with Oscar Scherer State Park, Nokomis Beach, Venice Beach and historic downtown Venice all nearby. Schedule your private showing and come see what makes this home and its waterfront setting so special.

18050 Wooden Skiff Court, Nokomis

$4,795,000

Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$4,795,000

2 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property. On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast. Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard. The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting. Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep. 2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.

2417 Casey Key Road, Nokomis

$2,095,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

154 Lookout Point Drive, Osprey

5100 Jessie Harbor Drive Unit 404, Osprey

$599,000

2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

$28,900

Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code

The industrious Gulf Harbor Marina is a very ideal spot to keep your best vessel high and dry until you are ready to splash in and go! N-60 is 9.8W X 25L X 8H, and can hold a vessel that is 8.8W, 24L and 7H, it is on the bottom rack and is easy for an owner to access their boat for quick maintenance needs and an even quicker drop in to your next water adventure. Gulf Harbor Marina is a perfect spot to keep your vessel in between uses that is next to fabulous water front restaurants, it has beautiful updated facilities, a bait shop with frozen or live bait (squid, shrimp, sardines and chum), fish cleaning tables with connected water, and a shaded gazebo for those to wait for their vessel in the shade. The marina also has a service center with lots of parts, they can order anything you need for your boat and even do repairs and installs, but if you are a do it yourself person, there are work racks where you can work on your own with day time use of electrical hook up. There is an easy phone app called speedy dock where you can schedule your splash times in advance 8:15AM-4pm, and you can have as many drop ins at no charge, just need to request it in the app. On site they carry diesel and Rec 90 fuels. There are multiple 30,000lb lifts to get boats in and out safely and quickly. There are 24/7, 365 security cameras. You will need to have 300k in liability insurance for your vessel with Gulf Harbor Marina as an intercept party. the rooftop of the storage building is open for great air flow. Plenty of parking on site for easy loading and unloading. The marina staff are extremely friendly and eager to help and provide excellent customer service.

100 Circuit Road Unit N60, Nokomis

$784,000

3 Beds ⋅ 2 Baths ⋅ Inlets SubDv. ⋅ 34275 Zip Code

Virtually Staged. 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

$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

$23,000

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

7204 Jessie Harbor Drive Unit 7204, Osprey

$395,000

2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

Osprey/Nokomis Homes with Sailboat Water Water Frontage

Newest Osprey/Nokomis Homes with Sailboat Water Water Frontage