Osprey/Nokomis Homes with Boatable Water Water Frontage

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

Gulf-Access Waterfront Living in Nokomis, Florida. Built in 2018, this Key West-style home pairs newer construction with a private 25-foot dock, 7,000-pound boat lift and Gulf access from your own backyard, all in a peaceful, natural setting along Curry Creek. This two-bedroom plus den, two-bath waterfront home offers the rare chance to enjoy true Old Florida privacy, with native mangroves, water birds and abundant wildlife right outside your door. Step onto your dock and spend the day on the water with your boat, jet skis, kayaks, paddleboards or pontoon. From Curry Creek, cruise into Roberts Bay and out to the Gulf of Mexico through the Venice Jetty. Exceptional construction sets this home apart, with concrete-block construction, fiber-cement siding, PGT hurricane-impact windows, a high-quality metal roof, an attached two-car garage with a reinforced garage door, and extensive foam insulation throughout the attic and walls. Inside, the open floor plan was designed for relaxed Florida living and entertaining. The heart of the home is the beautifully appointed kitchen, featuring granite countertops, KitchenAid stainless steel appliances, a breakfast bar and generous cabinetry, all flowing seamlessly into the main living area. Sliding glass doors open completely to the screened lanai, extending the living space outdoors and bringing the waterfront setting in. French doors lead to a versatile den, perfect for a home office, quiet retreat or additional sleeping space for guests. Tray ceilings, crown molding and a custom walk-in closet in the primary suite complete the interior. The screened paver lanai overlooks the natural waterfront setting, with a wooded path leading directly to your private dock. Cottages of Curry Creek is an intimate gated community of just 12 waterfront homes with low HOA fees that include lawn maintenance and irrigation. The Legacy Trail is less than half a mile away, with Nokomis Beach, Venice Beach, historic downtown Venice, shopping, dining and I-75 all just minutes from home. This is your chance to own a slice of paradise and enjoy the beauty of waterfront living in the Florida sunshine.

18050 Wooden Skiff Court, Nokomis

$1,399,000

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

Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, Osprey

$525,000

Bay Point SubDv. ⋅ 34275 Zip Code

Newly available 0.27-acre waterfront lot directly on Dona Bay, offering a rare opportunity to build your own custom home in beautiful Nokomis. Enjoy the best of Florida coastal living with convenient access to Nokomis Beach, Casey Key, and the Gulf of Mexico, along with waterfront dining, local restaurants, marinas, and outdoor recreation nearby. Ideally positioned between Venice and Sarasota, this property offers a peaceful waterfront setting while keeping shopping, dining, entertainment, and cultural attractions within easy reach. Build your dream home and enjoy breathtaking bayfront surroundings, coastal breezes, and the relaxed lifestyle that makes Nokomis such a sought-after destination.

114 Magnolia Avenue, 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

$279,000

Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code

Rarely available oversized indoor, covered, hurricane-protected boat slip at Gulf Harbor Marina in Venice! Measuring an impressive 40' L x 19' W x 15' H, this slip accommodates vessels up to 39.5' L x 18' W x 13.5' H, offering exceptional space for larger boats that can be difficult to accommodate in traditional dry storage. Located just minutes from the Venice Jetty and Gulf of Mexico with no bridges to navigate, Gulf Harbor provides outstanding convenience and quick access to open water. Enjoy remarkably low HOA fees of just $399 per month, the same fee charged for every slip in the marina, regardless of size, making this oversized slip an exceptional value. A rare opportunity to own secure, protected boat storage with generous dimensions and an ideal Gulf access location.

100 Circuit Road Unit S62, Nokomis

$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

$2,199,999

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

$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

$3,650,000

4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Tucked away at the end of Cutlass Bayou, this extraordinary 1.2-acre private peninsula offers a setting that is increasingly difficult to find on Casey Key. Completely redone and sold furnished this property is Surrounded by water on three sides with approximately 900 feet of shoreline, the property feels like its own secluded island retreat, with sweeping bay views, protected water, mature tropical landscaping, and deeded access to the sandy beaches of the Gulf of Mexico. The property is anchored by a charming 1950 main residence with a separate guest suite, accompanied by a distinctive 1968 artist studio designed by noted architect Edward “Tim” Seibert", an important contributor to Sarasota’s celebrated mid-century modern architectural movement. Together, the structures offer a glimpse into the architectural character that has long made Casey Key so special. Wander beneath a canopy of mature trees along the southern shoreline, where meandering trails lead to a peaceful waterfront deck—a quiet place to read, relax, or simply enjoy the shade and solitude. On the northwest point, wide-open bay views provide the backdrop for a waterfront Tiki hut with an outdoor kitchen and bar, ideal for sunset cocktails, entertaining friends, or preparing the day’s fresh catch. Just steps from the main residence, the bayfront swimming poo overlooks the water and offers the perfect place to cool off after a day of boating, fishing, paddleboarding, or exploring the Intracoastal Waterway. Along the protected northern harbor of the bayou, plans are available for a proposed substantial new dock, creating exciting possibilities for the boating enthusiast. And when the Gulf is calling, simply cross Casey Key Road to your deeded Gulf beach easement and enjoy the sand, surf, and spectacular sunsets that define the Casey Key lifestyle. The opportunity here is as remarkable as the setting. With 1.2 acres, extraordinary shoreline, Gulf access, bayfront living, and remarkable privacy, the possibilities are compelling. Located on desirable Casey Key, between Siesta Key and the Island of Venice, the property offers a rare combination of seclusion and convenience. Blackburn Point Road provides easy access on and off the island, while restaurants, boutiques, shopping, Sarasota, Venice, and I-75 are all within convenient reach. A magical lane. A private peninsula. Bay on three sides and the Gulf just across the road. This is more than a waterfront property—it is an opportunity to create your own legacy on Casey Key.

3780 Cutlass Bayou Road, Nokomis

$349,900

3 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code

Expansive lake views await you on the largest condo lake in Toscana Isles! With a brand new roof, this bright and airy 3-bedroom plus den condo is ideally situated to offer stunning, unforgettable views, and it comes fully furnished! This spacious floor plan features an open kitchen complete with a large center island, white cabinets with 42-inch upper cabinets, granite countertops, a stylish backsplash, stainless steel appliances, an upgraded Bosch dishwasher, and a generous walk-in pantry. Additional upgrades include motorized lanai shades, new lighting in the living area, designer ceiling fans, a UV light in the HVAC system, blinds, and window coverings. The owner's suite boasts an en-suite bathroom with double sinks, a walk-in shower, and a walk-in closet. The two additional bedrooms are located at the front of the unit, providing privacy for your guests. Finishes throughout the main living area and den include large neutral tiles installed diagonally, complemented by designer paint for a coastal ambiance. Relax and unwind on your spacious screened balcony as you take in the exceptional lake views and shimmering waters, enhanced by the sought after bright southeast exposure. Toscana Isles is a gated, resort-style community that focuses on an active lifestyle with landscape maintenance included. Enjoy kayaking, canoeing, and fishing on over 200 acres of interconnected lakes, right from your backyard. The 8,000-square-foot clubhouse features a fitness center, ballroom, billiard room with a big-screen TV, and courts for tennis, pickleball, and bocce. Toscana Isles offers easy access to the beautiful Suncoast Beaches, just 10 minutes away, as well as the Legacy Bike Trail and the vibrant downtowns of Venice and Sarasota, which boast a rich cultural life, excellent shopping, and gourmet restaurants. And, Sarasota Memorial Hospital recently opened its new Venice campus nearby. Call today for a private showing! New roofs are currently being installed on the condominiums.

130 Porta Vecchio Bend Unit 202, Nokomis

$49,000

Gulf Harbor Marina SubDv. ⋅ 34275 Zip Code

Rarely available extra wide indoor, covered, hurricane-protected boat slip N-21 at Gulf Harbor Marina in Venice! Measuring 25' L x 17.5' W x 11' H, this slip accommodates vessels up to 24.5' L x 16.5' W x 9.5' H, offering exceptional width for a variety of boats. Located just minutes from the Venice Jetty and Gulf of Mexico with no bridges to navigate, Gulf Harbor provides outstanding convenience and quick access to open water. Enjoy low HOA fees of just $399 per month. A rare opportunity to own secure, protected boat storage in an ideal Gulf-access location.

100 Circuit Road Unit N21, Nokomis

Osprey/Nokomis Homes with Boatable Water Water Frontage

Newest Osprey/Nokomis Homes with Boatable Water Water Frontage