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

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

111 Clipper Way Unit 111, Nokomis
$349,000
2 Beds ⋅ 2 Baths ⋅ Fairway Village SubDv. ⋅ 34275 Zip Code
EVERYTHING NEW + NOKOMIS BEACH LIFESTYLE + LOCATION, LOCATION, LOCATION= EXCEPTIONAL VALUE AT $349,000! Why buy an older Florida property and immediately start spending money upgrading it? At 111 Clipper Way, the improvements have already been made. This beautifully updated 2-bedroom, 2-bath, approximately 1,116-square-foot end-unit villa in the waterfront 55+ community of Fairwinds Village combines the comfort of an extensively improved residence with one of the things Florida buyers value most: LOCATION. Featuring NEW hurricane-impact windows and doors, NEW appliances, NEW A/C, and extensive updates throughout, this home has been positioned for the buyer who wants to move in and enjoy Florida rather than immediately take on another renovation project. Step outside and the lifestyle becomes just as impressive. Fairwinds Village offers a community pool, clubhouse, recreational amenities, private boat ramp, and waterfront access to saltwater canals and the Intracoastal Waterway. Previous listings have also promoted the home's ability to walk or bike to Nokomis Beach. With single-story living, two full bathrooms, covered parking, a screened outdoor living area, and a desirable corner/end-unit location, this residence delivers many of the features today's Florida buyer is searching for. Offered at $349,000, this property represents more than square footage. It represents the value of improvements already completed, major systems already replaced, hurricane protection already installed, and a coastal Florida lifestyle ready to enjoy. Move in. Unpack. Head to the beach. Welcome home to 111 Clipper Way. Call your favorite Realtor® today for a quick showing

111 Clipper Way Unit 111, Nokomis

516 Tamiami Trail S Unit 201, Nokomis
$759,000
2 Beds ⋅ 3 Baths ⋅ The Harbor Villas At Dona Bay SubDv. ⋅ 34275 Zip Code
LUXURY WATERFRONT RESIDENCE | FULLY REIMAGINED | PRIVATE END-POSITION BOAT SLIP | EXCEPTIONAL SUNSET VIEWS Welcome to Harbor Villas at Dona Bay, where exclusive coastal living meets exceptional waterfront amenities and the confidence of a proactively maintained condominium community. Tucked away in a quiet, private corner of the building, this beautifully remodeled, west-facing residence offers more than 1,800 square feet of refined living space, spectacular sunset views, two bedrooms, two-and-a-half baths, and a highly desirable deeded end-position boat slip. Step inside to discover a bright, open contemporary interior, where expansive windows and sliding glass doors fill the residence with natural light while framing beautiful views of Dona Bay. Thoughtfully redesigned throughout, the home features large-format concrete-look tile flooring, fresh designer paint, custom lighting, new ceiling fans, upgraded interior doors, baseboards, and trim. The stunning new kitchen showcases an all-new appliance suite and sophisticated finishes, ideal for both everyday living and entertaining. Impact-resistant windows and doors provide added protection, energy efficiency, and comfort. The spacious primary suite offers breathtaking water views and a luxurious spa-inspired bath featuring a wet room, soaking tub, new vanity, and elegant finishes. Guests enjoy a beautifully appointed second bedroom with its own remodeled en-suite bath, while a striking powder room adds a designer touch. An expansive covered balcony with desirable western exposure provides the perfect setting to relax and enjoy magnificent Florida sunsets over the bay. A BOATER'S ADVANTAGE: Included with the residence is a highly desirable deeded end-position boat slip, offering an exceptional waterfront amenity with convenient access to the Intracoastal Waterway and Gulf of Mexico, with no fixed bridges. The owner has already funded and submitted an application for a proposed slip extension designed to accommodate a boat approximately 28 feet in length, subject to regulatory and association approvals. This planned improvement offers exciting potential for boating enthusiasts seeking additional flexibility. A COMMUNITY INVESTED IN ITS FUTURE: Harbor Villas at Dona Bay has proactively addressed significant preventative maintenance and capital improvements, successfully completing its required Florida Milestone Structural Inspections and Structural Integrity Reserve Study (SIRS). Recent enhancements include freshly painted building exteriors, refreshed tropical landscaping, and newly paved parking areas. Additionally, the community's dock renovation project is fully funded. These improvements reflect the association's commitment to maintaining its waterfront property, infrastructure, and long-term appeal. Residents enjoy a waterfront lifestyle with a community swimming pool, fitness center, covered parking, and beautifully maintained grounds. Conveniently located just minutes from Nokomis Beach, Historic Downtown Venice, waterfront dining, shopping, and recreation, this exceptional residence combines the privacy of a quiet corner location, the beauty of western waterfront views, and the advantages of a well-maintained coastal community. Beautifully renovated. Exceptional boating access. Proactive community investment. Experience waterfront living at Harbor Villas at Dona Bay.

516 Tamiami Trail S Unit 201, Nokomis

39 Crown Point Drive, Nokomis
$128,500
1 Beds ⋅ 1 Baths ⋅ Kings Gate Club SubDv. ⋅ 34275 Zip Code
LOCATION, LIFESTYLE & LAND OWNERSHIP! Welcome to Kings Gate Park, a gated, waterfront-access 55+ community offering the rare advantage of fee-simple ownership, where you own both your home and the land! Boating enthusiasts will appreciate access to the Intracoastal Waterway and Gulf of America with just three fixed bridges along the route. The private ramp includes a dock with cleaning station. If you're looking for low-maintenance living in a welcoming, active community with a friendly, neighborhood atmosphere, this is the perfect place to call home! This charming 1-bedroom, 1-bathroom residence offers comfortable, easy living with the added bonus of a solidly constructed, 216-square-foot Florida/three-season room, built just three years ago. Complete with a portable A/C unit for nearly year-round enjoyment, this versatile space is ideal for relaxing, entertaining, or accommodating guests. Together, the home and Florida Room offer approximately 624 square feet of combined living space. Inside, you'll appreciate the convenience of a propane gas stove, supplied by an easily accessible, exterior 30-gallon propane tank. Additional improvements include an HVAC system replaced in 2021, newer windows throughout most of the home, an updated bathroom vanity, a replacement bedroom ceiling fan, and a newer microwave. The lifestyle is where Kings Gate Park truly shines! The HOA fee includes water, sewer, internet, cable TV, and lawn maintenance, allowing you more time to enjoy the exceptional community amenities. Residents have access to a private boat ramp, boat and trailer storage, swimming pool, pickle ball and tennis courts, shuffleboard, bocce, a fully equipped woodworking shop, garden shed with tools, billiards room, community grills, and a craft room. The clubhouse is a hub of activity, offering social gatherings, games, cards, and opportunities to connect with neighbors. Whether you enjoy boating, staying active, socializing, or simply relaxing in the Florida sunshine, Kings Gate Park offers a wonderful opportunity to embrace the Florida lifestyle. Own your land, enjoy the amenities, and make every day feel like a vacation!

39 Crown Point Drive, Nokomis

108 Sunrise Drive, Nokomis
$1,369,999
4 Beds ⋅ 3 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
RARE GULF WATERFRONT GEM ON ROBERTS BAY! Welcome to 108 Sunrise Drive, where sparkling bay waters, coastal breezes, lush tropical landscaping, and an exceptional waterfront setting come together to create a truly unique opportunity in Nokomis. Offering approximately 75 feet of waterfront, an existing dock, Gulf-access boating with no bridges, and a beautifully paved and landscaped shoreline, this property delivers the kind of coastal setting that is increasingly difficult to replicate. Just minutes from beautiful Gulf Coast beaches, with boating access leading toward the open Gulf, the location captures everything buyers love about Florida waterfront living — peaceful water views, boating from your own backyard, warm coastal sunsets, and easy access to the sand and sea. The waterfront area is one of the property’s standout features, with attractive paving, established landscaping, dock access, and a serene setting overlooking Roberts Bay. Imagine morning coffee beside the water, afternoons on the boat, and evenings enjoying glowing sunsets and gentle coastal breezes from your own property. For builders and buyers with vision, the opportunity is substantial. Renovate and reimagine the existing residence, explore the flexibility of the additional rear living spaces, or create a spectacular custom waterfront residence designed to fully take advantage of the setting. For the buyer searching for a Florida vacation home, boating retreat, investment, or forever home, this is a chance to create something extraordinary — a custom coastal residence with expansive outdoor living, a resort-style front yard, sweeping water views, and your boat just steps from the door. The main residence is currently gutted and ready for renovation, reconfiguration, or complete redevelopment to maximize this exceptional waterfront site. The true value lies in what cannot easily be recreated: waterfront land, dockage, boating access, proximity to the open Gulf and beaches, mature landscaping, and an incredible canvas for renovation or new construction. Bring your builder. Bring your architect. Bring your vision. 108 Sunrise Drive Nokomis — where waterfront living, coastal beauty, and exceptional potential meet.

108 Sunrise Drive, Nokomis

2115 Lychee Lane, Nokomis
$4,485,000
4 Beds ⋅ 6 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
RARE BLACKBURN BAY WATERFRONT ESTATE | 119' DEEP-WATER FRONTAGE | PRIVATE DOCK | NO-BRIDGE GULF ACCESS Privately gated and beautifully positioned along Blackburn Bay, 2115 Lychee Lane is a rare waterfront estate offering privacy, refined living and an exceptional boating lifestyle. Set on approximately 0.58 acres with 119 feet of deep-water frontage, this three-home enclave has no monthly HOA and offers easy, no-bridge access toward the Gulf. With over 6,000 square feet of living space, the residence features expansive bay views, custom architectural details, crown molding, tray ceilings, 5-inch baseboards and 24x24 porcelain tile. The dramatic 2024 chef’s kitchen showcases custom floor-to-ceiling cabinetry, granite surfaces and Wolf, Sub-Zero and Cove appliances, opening to the dining room with fireplace and sweeping water views. The expansive family room with custom oak bar flows seamlessly to the waterfront entertaining areas. The first-floor primary suite offers panoramic water views, private terrace, generous bath and custom walk-in closet, complemented by a formal sitting area and office. A second primary suite upstairs features a private balcony, marble en-suite bath and two custom walk-in closets, with additional en-suite bedrooms for family and guests. Outdoor living is exceptional with a heated pool, spa, waterfall, outdoor kitchen, fireplace and expansive covered and open-air living areas overlooking Blackburn Bay. A private beach and firepit create an idyllic waterfront retreat. Boaters will appreciate the newly constructed deep-water dock with composite decking, 14,000-lb. boat lift, two jet-ski lifts, electricity and water, plus no-bridge Gulf access. Additional enhancements include impact-rated windows and doors, electric shutters, whole-home Generac generator, security and camera systems, automated blinds, programmable HVAC, commercial whole-house water filtration, irrigation well and a newly constructed elevated three-car garage with air conditioning. At 2115 Lychee Lane, Blackburn Bay is more than a backdrop—it is the lifestyle.

2115 Lychee Lane, Nokomis

1716 Casey Key Road, Nokomis
$12,650,000
4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
Spanning nearly an acre from the Gulf of Mexico to Blackburn Bay, this one-of-a-kind Casey Key residence pairs 140 feet of private Gulf frontage with 130 feet of protected bayfront, offering private beach access, boating and sweeping water views from sunrise to sunset. Designed by Jerry Sparkman, AIA, NCARB, of Sweet Sparkman Architecture and completed in 2021, the residence blends architecture and nature, land and water, and linear and curved forms. Its elevated "split-level hugger" design combines a split-level floor plan with a modified courtyard concept, creating intimate gathering spaces and a seamless indoor-outdoor connection. Flowing rooflines, curved walls and broad overhangs form a sculptural silhouette, while warm wood ceilings and walls of glass fill the interiors with natural light and frame the Gulf, Blackburn Bay and tropical landscape in nearly every direction. The light-filled interior is centered around an open great room, dining room and kitchen, where soaring wood ceilings, oversized windows and expansive glass doors open to an elevated waterfront terrace. A separate lounge with a bar offers an inviting space for entertaining, while a waterfront fitness space opens directly to the lawn and bay. Upstairs, the primary suite is wrapped in floor-to-ceiling glass and features a private terrace with uninterrupted Blackburn Bay views. Its spa-inspired bath includes a floating dual vanity, freestanding soaking tub, glass-enclosed shower and corner windows overlooking the water. Three additional bedrooms accommodate family and guests, while the loft provides flexible living space. An elevator connects the home's levels for added convenience. Designed for coastal living, the residence unfolds around a private oasis with a resort-style pool, expansive terraces and shaded lounge areas. Curved stairways and elevated walkways wrap through the architecture, offering changing perspectives of the pool, lawn, bay and Gulf. Covered entertaining spaces provide comfortable places to gather out of the sun, while the open lawn extends toward the bayfront and private dock. From morning on the water to sunset over the Gulf, the property offers a seamless waterfront lifestyle. The residence has also earned NGBS Emerald certification, the highest tier under the National Green Building Standard, along with a RESNET HERS Index rating of -28, a score below zero means the home produces more energy than it consumes, powered in part by on-site solar. It's a rare combination of coastal luxury and true net-positive energy performance. The Gulf-to-Bay setting is essential to the experience. The private dock and boat lift provide direct access to Blackburn Bay, the Intracoastal Waterway and the Gulf. On the west, sunset views are just steps from the beach. A refined palette of stucco, glass, wood and concrete balances architectural sophistication with coastal durability. Native beach grasses, sea grapes and palms soften the transition between the home and its island landscape. Elevated to meet FEMA floodplain requirements and coastal-resiliency standards, the residence responds thoughtfully to its barrier-island setting. Located on Casey Key, it offers exceptional seclusion without sacrificing convenience. The property is positioned between Sarasota and Venice, near historic downtown Venice, Nokomis Beach and waterfront dining, with convenient access to Sarasota International Airport and downtown Sarasota.

1716 Casey Key Road, Nokomis

366 S Creek Court, Osprey
$1,049,000
4 Beds ⋅ 3 Baths ⋅ South Creek SubDv. ⋅ 34229 Zip Code
Welcome to 366 South Creek Court, located in the highly sought-after gated waterfront community of South Creek in Osprey, Florida. Nearly completely renovated, this beautiful 4-bedroom, 3-bathroom home offers 2,775 square feet of thoughtfully designed living space, combining elegant finishes, comfortable living spaces, and exceptional indoor-outdoor living. The open and bright floor plan features separate living and dining areas, a spacious family room, and a charming dinette overlooking the lanai and backyard. Luxury details throughout include tray ceilings, crown molding, rounded wall edges, plantation shutters, 8-foot doors, arched doorways, and engineered hardwood flooring. Fresh interior paint and expansive windows and doors fill the home with natural light. At the heart of the home is the beautifully renovated kitchen, featuring 42-inch shaker-style soft-close cabinetry with crown molding, deep drawers, stainless steel appliances, induction cooking, a hood vent, dual-bowl sink, and quality hardware. Vibrant quartz countertops and an oversized island with seating create an inviting space for everyday living and entertaining. The front living area provides a welcoming setting for conversation or relaxing with a book beside the electric fireplace with solid wood mantel. Adjacent to the living space is a dedicated dining area with a wet bar and wine chiller, ideal for entertaining family and guests. The spacious primary suite offers abundant natural light and direct access to the screened lanai. The ensuite features dual vanities, a dedicated makeup counter and seat, generous counter space, dual walk-in closets, and a brand-new oversized custom walk-in shower. Three additional guest bedrooms offer excellent closet space and natural light. The first guest bath combines a large walk-in shower with a conveniently located laundry area featuring a stackable washer and dryer. The second guest bath offers a dual vanity, tub/shower combination, and adjacent linen closet. Outdoor living takes center stage with a covered and screened paver lanai featuring a heated pool and spa. The lush, mature landscaping and areca palm-lined backyard provide a private and tranquil setting. An additional exterior patio has been designed to accommodate a 72-inch outdoor kitchen, creating an ideal space for entertaining. The home welcomes guests with a paver driveway and sidewalk leading to a charming country-style front porch. The oversized two-car extended garage features ceiling storage racks, a side-entry door, and a hurricane-rated garage door. Additional exterior improvements include fresh paint, new lighting, security cameras, beautiful landscaping, an irrigation system, and hurricane storm panels for every opening. South Creek offers a low HOA fee and an exceptional collection of amenities, including a kayak launch, tennis and pickleball courts, basketball court, and community boat and fishing dock on the South Creek saltwater canal. Ideally located near Casey Key, Nokomis and Siesta Key beaches, Pine View School, shopping, restaurants, a dog park, and the Legacy Trail. Located in an X flood zone, flood insurance is optional. This beautifully renovated South Creek home offers the perfect combination of style, privacy, amenities, and coastal Florida living.

366 S Creek Court, Osprey

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