Longboat Key Homes with Sailboat Water Water Frontage

Longboat Key Homes with Sailboat Water Water Frontage

Welcome to Longboat Key, a stunning barrier island located in the beautiful state of Florida. Known for its pristine beaches, luxurious resorts, and world-class golf courses, Longboat Key is a true paradise for those seeking a waterfront lifestyle.

One of the most coveted features of this region is the abundance of homes with sailboat water frontage. If you are a boating enthusiast or simply enjoy the tranquility of living by the water, Longboat Key offers an array of homes that cater to your desires. Imagine waking up to the gentle sounds of waves lapping against your private dock, ready to set sail on your sailboat whenever the mood strikes.

Whether you are looking for a cozy beachfront cottage or a grand estate, Longboat Key has a diverse range of properties to suit every taste and budget. From modern architectural marvels to charming Mediterranean-style villas, each home is designed to maximize the breathtaking water views and provide an unparalleled waterfront living experience.

Living in a home with sailboat water frontage not only offers the convenience of having your boat at your doorstep but also provides endless opportunities for water-based activities such as fishing, kayaking, and paddleboarding. Additionally, you can take advantage of the region's vibrant boating community, where you can socialize with fellow boaters and participate in various events and regattas.

Longboat Key truly embodies the epitome of coastal living, where you can indulge in the serenity of the water while being surrounded by the natural beauty of the island. So, if you are dreaming of a home with sailboat water frontage, look no further than Longboat Key, where paradise awaits.

Newest Longboat Key Homes with Sailboat Water Water Frontage

$575,000
2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code
Gorgeous two-bedroom walk-out bayfront unit in Pelican Harbour & Beach Club. Pelican Harbour offers one of the best amenity packages on the island, including private beach with chairs and loungers, heated resort-style pool, owner boat docks, kayak and bike storage, tennis, pickleball, clubroom, and more. The Association also has successfully completed its Milestone Inspection, has fully-funded reserves, and no special assessments. You'll also appreciate the new roofs, new hurricane rated carports, freshly painted buildings, new seawall, and composite docking. The unit itself offers bayfront walk-out convenience, screened lanai, open floor plan with large great room and dining, kitchen with updates and stainless appliances, comfortable guest suite with access to full bath, and a spacious primary suite with a private bath en-suite. Association fees include maintenance, landscaping, building insurances, cable, water, trash, on-site maintenance, professional management, most amenities, pest control, and more. Boat docks can accommodate boats up to 28'. Dock fees are $20 per foot per year - a 25' boat would be $500/year. Pelican Harbour is a pet-friendly community and your furry friend is welcome. Pelican Harbour is perfectly located mid-island with easy access to Bayfront Park, grocery, shopping, restaurants, places of worship, and convenient to St Armands and Sarasota. Pelican Harbour - well-managed, fully funded, amenity rich, and steps to the beach - offers one of the most affordable maintenance-free island-lifestyles available on Longboat Key.

4234 Gulf Of Mexico Drive Unit J1, Longboat Key
$549,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
A Boater's Dream- Get a Century 19 feet Bay Boat INCLUDED with a Full price contract !Island waterfront affordable living in an updated relaxing coastal setting. Updates include, impact sliding doors and windows with shades, new kitchen with quartz countertops, water softener, updated walk in bath (master with bidet) , tile flooring, newer AC ( 2 years plus ) with transferable warranty. For your convenience and comfort, the master bedroom has Tempur-Pedic cool gel bedding and custom-built cabinetry. The location is a boater’s dream where spending every day on the water is a reality from the optimal docks featuring water and electricity for up to 34-foot vessels on deep sailboat or powerboat accessible waters, available for a yearly fee on a first come basis. The amenity-rich community includes four heated pools, tennis and pickleball courts, a spacious fitness center & sauna, mini-golf, kayaks, paddleboard and bike storage, lounge and on-site HOA management. Residents enjoy the privilege of a private gated beach pavilion on the gulf with parking, beach chair storage, restrooms and showers. Experience maintenance-free, coastal living at its finest in this lovely spacious residence with easy access to St. Armands Circle's for shopping and dining as well as a short ride over the bridge to the Sarasota/Bradenton International Airport or to enjoy downtown Sarasota's Bayfront marina and park, cultural and theater venues, and downtown's lively city vibe.

4390 Exeter Drive Unit I303, Longboat Key
$315,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Located on Q dock at the picturesque Longboat Key Marina, the 55’ x 21’ deep water Boat Slip has one of the largest turning basins available for easy maneuvering and some of the most stunning views. The marina is perfectly positioned on the coveted island of Longboat Key, Florida’s spectacular Gulf Coast. Very close proximity to the intracoastal waterway provides quick access to deep sea fishing and boating. Moments to Publix supermarket, CVS, Chase Bank, the post office, public tennis courts and more. The Marina amenities include wifi, water, laundry facilities, pump out and a shuttle service to the restaurants and boutiques of the fabulous St Armands Circle. This slip is not covenanted, meaning membership to the Longboat Key Club is not required with the purchase of slip Q-5. However membership is optional to the surrounding Golf courses and the beach club of LBK Club and separately to the Bay Isles Beach Club which also offers direct access to the spectacular beaches and turquoise waters of the Gulf. A world class Marina with exceptional service and amazing proximity to everything required for ease and maximizing the boating lifestyle. A truly gorgeous setting in an A+ location.

2600 Harbourside Drive Unit Q5, Longboat Key
$529,000
3 Beds ⋅ 2 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code
Welcome to Sutton Place, a beautifully maintained 3-bedroom, 2-bathroom residence located on the prestigious island of Longboat Key. This charming home offers 1,198 sq. ft. of living space with access to Sarasota Bay. With water access, including a fishing pier and sailboat water, this property is perfect for those who enjoy a true waterfront lifestyle. This welcoming community offers plentiful amenities, including deeded access to a Gulf front beach club with gated parking and a Beach Pavilion featuring restrooms, showers, picnic tables, and first-come chair storage for only $30/year. Sutton Place also includes two heated pools, BBQ grills, social activities, a fishing dock, bike racks, and an enclosed storage room. For boating enthusiasts, there are boat slips available on a first-come, first-serve basis for a nominal $300/year, along with kayak storage and a kayak lift and launch. Residents also enjoy a clubhouse, community laundry, and one deeded covered parking spot, plus ample guest parking. The residence’s mid-key location offers easy access to Bayfront Park, a local favorite for outdoor activities. The park features a playground, basketball and shuffleboard courts, a multi-purpose open field, pickleball and tennis courts, picnic tables, and a yoga lawn—providing endless opportunities for recreation and relaxation. Longboat Key offers an unparalleled lifestyle, featuring pristine beaches, championship golf courses, tennis facilities, nature parks, and scenic biking and walking paths. Residents can indulge in world-class dining, boutique shopping, and cultural attractions just minutes away in St. Armands Circle and downtown Sarasota. With easy access to the best of Longboat Key and just a short distance from the beach, this property offers the perfect opportunity to enjoy island living at its finest.

569 Sutton Place, Longboat Key
$325,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Reciprocity with 700 other yacht clubs across America. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-16, Longboat Key
$400,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
70 x 21 Boat Slip on R-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline LBK Club membership is optional. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 65 LOA.

2600 Harbourside Drive Unit R-07, Longboat Key
$299,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
This 60' x 20' boat slip at The Longboat Key Club Moorings Marina is truly a gem for any boating enthusiast. Located in one of the premier protected deep-water yacht marinas on Florida’s West Coast, it offers seamless access to the Intracoastal Waterway, open bay, and the Gulf of Mexico, making it an ideal spot for quick and easy departures. The slip's prime location within the marina provides convenience to top-notch amenities. You’ll be near the exclusive clubhouse with its private pool and grills, while the marina village, offering another pool, restaurant, laundry facilities, marina office, ship's store, and pickleball courts, is just a short distance away. The marina itself is fully equipped with a range of services, including an onsite fuel dock, a dedicated dock master and crew for assistance, pump-out services, onsite maintenance, concierge, shuttle service, roving guard, and 24-hour guarded gate. A Yacht Club Membership is required, which opens up a wealth of benefits at The Longboat Key Club Resort. This includes access to 45 holes of golf, tennis courts, five restaurants, a spa, a fitness center, beachfront pool and beach facilities, holiday events, and the added advantage of reciprocity with 700 other yacht clubs across America. This slip isn’t just a place to dock your boat—it’s a gateway to a vibrant and luxurious boating lifestyle.

2800 Harbourside Drive Unit E10, Longboat Key
$685,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Welcome to your bay front condo on Longboat Key, where every day begins with breathtaking sunrises and panoramic views of Sarasota Bay. This updated 2-bedroom, 2-bathroom residence is designed for comfort, featuring easy to maintain tile throughout the main living spaces, creating a streamlined aesthetic. The open-concept great room flows seamlessly into the updated kitchen complete with stainless appliances, granite counters, and a westerly facing window for enjoying stunning sunsets over the Gulf of Mexico. Each evening, you'll also enjoy moonrises reflecting off the bay and gentle breezes over the serene waters from your 22-foot wall of floor-to-ceiling windows in the Florida room, a perfect backdrop for relaxation or entertaining. The primary bedroom, nestled at the far end of the home for privacy, offers more bay views, direct access to the Florida room, and a generously sized ensuite bathroom with walk-in closet and conveniently placed laundry. The second bedroom, equally serene, also boasts bay views, direct access to the Florida room, and is served by an adjacent updated bathroom, ensuring comfort and privacy for your guests. This condo offers peace of mind with 2019 hurricane-rated windows, a 2019 HVAC system, and a 2019 water heater. Underbuilding parking and a private storage room provide additional convenience and value. Plus, one of the two community pools is just outside your front door, adding to the fun and ease of your tropical lifestyle. Located in the sought-after Windward Bay community, this lushly landscaped oasis is 26 acres and .5 mile long of direct bay front property, offering an unparalleled low density, serene living experience. There are fruit trees, walking/biking paths, picnic tables, and fire pits for your pleasure. Residents can also enjoy a wide range of amenities, including two boat basins with slips available for rent ($40/month or $45/month with an owner-supplied lift), kayak launches and storage ($35/year), fishing with fish cleaning stations, three beach accesses directly across the street, plus a large clubhouse with gathering space, catering kitchen, fitness center, locker rooms, and saunas. Additional recreational facilities include 2 heated pools with sundecks and complimentary chaises, shuffleboard, tennis, and pickleball courts. Ensuring peace of mind for years to come, this community is meticulously maintained with freshly painted buildings, new roofs, and a recently passed Milestone Integrity Inspection that certifies the buildings for another 10 years. The rental policy is flexible, with a one-month minimum or longer rental period allowed up to 2/year, and owners can rent immediately upon ownership without a waiting period. Beyond the on-site amenities, the unbeatable location is just a short drive from the restaurants, shops, and cultural activities of Saint Armands Circle and downtown Sarasota. For fine dining, the Zota Beach Resort is right across the street, and the nearby Centre Shops offer everything from Pilates and a diner to a seafood restaurant, ice cream shop, bank, and boutiques. With all special assessments already paid by the Seller, this condo represents an exceptional value and opportunity for any Buyer. Furnishings are optional if helpful to the Buyer.

4600 Gulf Of Mexico Drive Unit 202, Longboat Key
$420,000
1 Beds ⋅ 1 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Enjoy the epitome of coastal living nestled in the VIBRANT community of Longboat Harbour on beautiful Longboat Key. Don’t want to complete any projects or renovations? No problem, this UPDATED condo offers a luxurious living experience with abundant amenities and stunning bay views. Recent tastefully completed renovations include a new bathroom with high end finishes, updated kitchen, new doors and fresh paint throughout, a new primary closet, and window treatments that provide an interior that is both stylish and inviting. The open kitchen with stainless steel appliances, granite countertops, and beautiful shiplap mill work seamlessly open to the living and dining areas, maximizing space and comfort. Being offered FURNISHED (with new furniture and accessories with some exclusions), this residence is ready for immediate occupancy or rental. Need additional storage space? This condo also features a separate storage locker and a well-placed laundry facility (in-unit washers and dryers are also permitted). Located in a prime location within a gated community on Longboat Key, this property is a water-lover's paradise. Boating enthusiasts will appreciate the deep-water canal access to Sarasota Bay, with boat slips available on a first come basis and additional kayak launches. Longboat Harbour is renowned for its welcoming atmosphere and an array of amenities designed to cater to every interest and lifestyle. This resort like community with an on-site manager offers a range of recreational activities including mini-golf, shuffleboard, tennis, and pickleball. Fitness enthusiasts will appreciate the large and well-equipped fitness center, complete with private locker rooms and saunas. Additionally, the beautifully renovated recreation room overlooking the bay, serves as the heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, deeded beach access with a cabana, parking, restrooms, and dressing areas. Witness breathtaking sunrises, spot manatees, and savor stunning sunsets from this serene beachfront location. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's most active, social, and vibrant communities! Seize the opportunity to experience waterfront living at its finest. Schedule your private showing today.

4360 Chatham Drive Unit F204, Longboat Key
$549,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Overlooking Longboat Harbour and Sarasota Bay, this beautifully updated two-bedroom, two-bath condominium offers complete Longboat Key paradise living! This unit was updated in 2023. The kitchen boasts new appliances, stone countertops and shaker cabinets. It opens up to a great room with stunning water views. It is available for purchase turnkey. Longboat Harbour offers many community amenities, including boat docks in the community harbor, with slips available for rent based on availability. The harbor is well-protected, with docks accommodating boats up to 34 feet. Longboat Harbour also provides access to sailboat-depth water and easy access to the bay, the Intracoastal and Gulf of Mexico. Association fees cover access to the beach club, which is just a short distance from the units. The beach club features gated parking, private restrooms and showers, and sits on a beautiful stretch of white sand beach. Residents can also enjoy four waterfront heated pools, tennis and pickleball courts, waterfront recreational paths, a large fitness center, a newly renovated clubhouse with a full kitchen, and adequate space for meetings or social gatherings. The area is famous for kayaking, paddleboarding and observing marine and bird life, including dolphins, manatees, herons, osprey and eagles. Longboat Harbour employs a professional onsite management team and an onsite maintenance team and has fully funded reserves. Rentals are allowed with a minimum duration of one month. Whether you're drawn to the amenities, scenic views or the island lifestyle, Longboat Harbour offers a welcoming home for all.

4330 Falmouth Drive Unit C202, Longboat Key
$489,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Longboat Harbour offers a vast amount of community amenities, including boat docks, a kayak launch, pickleball courts, woodworking and art studios, and a beach club. This unit offers complete sprawling views of the harbor and Intracoastal waterway and is ready for you to make it your own! The harbor is well-protected, with docks that accommodate boats up to 34 feet. Longboat Harbour also provides access to sailboat-depth water and easy access to the bay, Intracoastal and Gulf of Mexico. Association fees cover access to the beach club, which is just steps away from the units. The beach club features gated parking, private restrooms and showers, and sits on a beautiful stretch of white sand beach. Residents can also enjoy four waterfront heated pools, tennis and pickleball courts, waterfront recreational paths, a large fitness center, a clubroom for social gatherings, a woodworking shop and an art studio. The area is popular for kayaking, paddleboarding, and observing marine and bird life, including dolphins, manatees, herons, osprey and eagles. Longboat Harbour also boasts a professional onsite management team, an onsite maintenance team and funded reserves. Rentals are allowed with a minimum duration of one month. Whether you're drawn to the amenities, the scenic views or island lifestyle, Longboat Harbour offers a welcoming home for all.

4340 Falmouth Drive Unit 203, Longboat Key
$850,000
3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Experience the epitome of Florida waterfront living at 750 St Judes Drive North! Nestled on a tranquil canal with no bridges to the Bay, this charming 3-bedroom, 2-bathroom split floor plan home offers 100 feet of canal frontage, complete with a private dock, davit, and an 16,000 lb boat lift - perfect for indulging in the boating lifestyle with ease. Buy your boat a home that you will love too! Boasting approximately 1200 square feet of air-conditioned living space, this property holds immense potential, being zoned multi-family, allowing for personal enjoyment or lucrative rental income opportunities. Relax in the expansive 500ft lanai and private pool area, offering an idyllic setting for entertaining guests as you look over your private dock and boat lift. Step inside to discover a well-maintained interior featuring modern upgrades including a new roof completed in 2016, along with an updated AC system and duct work in 2019, the pool was resurfaced in 2018, new electrical panel in 2019, and a tankless water heater installed in 2023, ensuring both comfort and efficiency year-round. The seawall was replaced in 2006, and if you are a boater, you know that is an incredible value. Conveniently located at the end of the canal on St Judes Drive North, this residence provides easy access to a myriad of dining and entertainment options such as Harry’s Continental Kitchen, Solorzano’s Pizza, and Euphemia Haye. If the beach is your vibe, residents enjoy exclusive beach access just a 5-minute stroll away, offering pristine white sands and panoramic views of the Gulf of Mexico. For outdoor enthusiasts, the proximity to Jew Fish Key and Bridge Street ensures effortless exploration of Sarasota Bay and beyond, while Joan Durante Park presents a tranquil retreat right in your backyard, boasting nature trails and scenic spots for relaxation. Don't miss the opportunity to make canal living your lifestyle - schedule your viewing today and seize the chance to own this exceptional waterfront retreat! The lanai is a peaceful retreat as well as an idyllic setting for entertaining guests. Private beach access just a stroll away to see sunsets is priceless. St Jude’s Dr N is unique. It is one of the friendliest neighborhoods on LBK with a true hometown feel.

750 Saint Judes Drive N, Longboat Key
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