Longboat Key Homes with Bay Front Water Frontage

Longboat Key Homes with Bay Front Water Frontage

Welcome to Longboat Key, Florida—a hidden gem nestled along the stunning Gulf Coast. This idyllic barrier island boasts pristine sandy beaches, lush landscapes, and a vibrant community that perfectly blends relaxation and recreation. Whether you’re seeking a serene retreat or an active lifestyle, Longboat Key has something for everyone.

One of the most enchanting aspects of Longboat Key is its exquisite waterfront properties. Imagine waking up to the gentle sound of waves lapping at your door, with breathtaking views of the bay right outside your window. Homes with bay front waterfrontage in Longboat Key offer a unique opportunity to embrace the beauty of coastal living. These residences provide not only a picturesque setting but also direct access to a myriad of water activities such as kayaking, paddleboarding, and fishing.

The luxurious homes here often feature spacious layouts, modern amenities, and outdoor living spaces designed for entertaining. Picture yourself hosting gatherings on your private patio, with sunsets painting the sky in vibrant hues as you enjoy the serene ambiance of your surroundings.

Longboat Key is not just about stunning homes; it’s also a community that values a laid-back lifestyle. With nearby gourmet dining, boutique shopping, and world-class golf courses, you’ll find everything you need just moments away. The island’s commitment to preserving its natural beauty and charm makes it a perfect place to call home.

If you’re considering a move to paradise, let Longboat Key’s bay front waterfront properties be your gateway to an extraordinary lifestyle filled with sun, sea, and serenity. Welcome to your dream home!

Newest Longboat Key Homes with Bay Front Water Frontage

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit B-16, Longboat Key

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. Wide views of Sarasota Bay, the Harbourside golf course and downtown Sarasota define this well-maintained 3-bedroom, 3.5-bath residence at Grand Bay. Floor-to-ceiling glass keeps the scenery in focus and brings natural light into the main living areas. The living room opens to a large terrace overlooking the golf course, bay and skyline, while tray ceilings and tile flooring contribute to the open feel. The kitchen features wood cabinetry, a center prep island, paneled refrigerator and adjoining dining area. Nearby, a sitting area includes textured accent walls and built-in shelving. The primary suite also opens to the terrace and offers bay views and an oversized walk-in closet. The adjoining bath includes a soaking tub, glass-enclosed shower and private water closet. Two additional guest suites each have an en suite bath, and an in-residence laundry room adds convenience. Grand Bay amenities include a clubhouse, two resort-style pools and spas, a fitness center with saunas and Har-Tru tennis courts, all within the gated Bay Isles community. Ownership also includes membership in the private Bay Isles Beach Club, with gated Gulf access, covered gathering and picnic areas, barbecue grills, restrooms and changing facilities. Optional membership in the Longboat Key Club is available separately. Depending on membership category, amenities may include 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining venues and lounges, beach and pool facilities, a spa, fitness and wellness facilities, member events and Longboat Key Club Moorings.

3040 Grand Bay Boulevard Unit 232, Longboat Key

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. Set within Grand Bay on Longboat Key, this renovated 3BR/3.5BA residence offers panoramic views of Sarasota Bay, the Harbourside golf course and the city skyline. With 2,250 square feet, walls of glass bring the scenery into nearly every main living space, creating an inviting blend of comfort, openness and relaxed Bay Isles elegance. Floor-to-ceiling windows with plantation shutters frame the views, while tile flooring, neutral tones and recessed lighting create a warm, understated setting. The living room opens to a wraparound terrace overlooking the golf course, a tranquil pond and Sarasota Bay - ideal for quiet mornings or entertaining. The kitchen flows easily into the living areas and features white cabinetry, stone countertops and backsplash, and stainless-steel appliances. The primary suite offers warm wood flooring and a spacious bath with dual vanities, a makeup area and a large walk-in shower. Two guest suites each include a private en suite bath. An in-residence laundry room and one covered parking space complete the home. Grand Bay residents enjoy a clubhouse, designer-appointed lobby, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Bay Isles privileges include gated entry, scenic walking paths and access to the private Gulf-front Bay Isles Beach Club, featuring white sand, an attended entrance, covered picnic and entertaining areas, tiki huts, barbecue grills, restrooms, changing rooms and beach-equipment storage. Optional membership is also available at the Longboat Key Club. Amenities vary by membership category and include 45 holes of championship golf, 20 Har-Tru tennis courts, private beach and pool facilities, spa and fitness facilities, restaurants and lounges, club events and marina access.

3040 Grand Bay Boulevard Unit 225, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

4390 Exeter Drive Unit 107, Longboat Key

Bay Isles SubDv. ⋅ 34228 Zip Code

Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities. Tucked behind double gated, guard-secured entry, this exceptional 0.41-acre homesite boasts an impressive 135 feet of deep-water frontage, offering effortless access to Sarasota Bay and the Gulf of Mexico. Designed for those who embrace the waterfront lifestyle, the expansive canal frontage provides possibilities for multiple vessels and seamless days on the water. As a Bay Isles resident, you'll also enjoy deeded private access to the Bay Isles Beach Club, where miles of pristine Gulf beaches await. Perfectly positioned directly across from the world-renowned St. Regis Longboat Key Resort, this premier location places luxury amenities at your doorstep while maintaining the privacy and exclusivity of a gated waterfront enclave. Championship golf, marinas, waterfront dining, boutique shopping at St. Armands Circle, and the arts, culture, and fine dining of downtown Sarasota are all just minutes away. Whether you envision a contemporary coastal masterpiece or a timeless waterfront retreat, this remarkable homesite offers the ideal canvas to build the custom residence you've always imagined in one of Southwest Florida's most distinguished waterfront communities. Architectural plans are available upon request, with engineering complete. Capitalize on the extensive development work already completed, saving valuable time and expense while accelerating the path toward permitting and construction. An existing residence is situated on the property; however, the property is being marketed for its exceptional homesite and development potential.

1600 Harbor Sound Drive, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Twin Shores Mobile Home SubDv. ⋅ 34228 Zip Code

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated over 6 feet, 2-bedroom, 2 bath, open floorplan home. HURRY and you can help design your new home and deck. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickleball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! RUN, don't walk, paradise awaits! *** Lot #96 is also available and under construction. ***

71 Twin Shores Boulevard, Longboat Key

4 Beds ⋅ 5 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.

657 Halyard Lane, Longboat Key

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. On the 3rd floor of Building One, this 3-bedroom, 3.5-bath residence opens to one of Longboat Key's signature views: the fairways and lagoons of the golf course in the foreground and Sarasota Bay stretching to the horizon beyond. A semi-private elevator landing opens to 2,369 square feet centered on a great room, where floor-to-ceiling sliders frame the water and open to a wide covered terrace. The living room and owner's suite both capture the bay-and-golf view and open to this terrace, while a second terrace off the kitchen overlooks the treetops and serves the two guest bedrooms. The kitchen features a center island, double wall ovens, and a built-in refrigerator. The owner's suite includes a custom walk-in closet and a marble bath with glass shower, soaking tub, and dual vanities, and one guest bedroom is fitted with a built-in desk and shelving for an easy home office. Original and ready for your finishes, it is a rare chance to make a bayfront retreat your own. Two deeded parking spaces and a private storage unit complete the offering. Behind the gates of Bay Isles, Grand Bay offers two heated pools, Har-Tru tennis, a fitness center, clubhouse, on-site management, and 24-hour security. Owners also receive deeded access to the private Bay Isles Beach Club on the Gulf. St. Armands Circle, downtown Sarasota, Harbourside golf and marina, and the beaches of Lido and Siesta Key are all minutes away.

3060 Grand Bay Boulevard Unit 133, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access. The redesigned interior features an open kitchen centered around a quartz waterfall edge island, soft close cabinetry, with all new stainless-steel appliances, including a wine refrigerator and a refrigerator with a built-in craft ice maker. Luxury vinyl plank flooring extends throughout the home, complemented by a smart thermostat for everyday convenience. Every room reflects the comprehensive renovation, and the home is further enhanced by a 2012 tile roof, new PGT hurricane impact windows, and sliding glass doors that open to a private paver patio overlooking a wooded landscaped setting. Spanish Main Yacht Club offers private deeded beach access to the Gulf of Mexico, a heated community pool, clubhouse, shuffleboard courts, and a pet-friendly environment. The community’s deepwater marina offers approximately 40 boat slips available for lease, accommodating vessels up to 40 feet with water and electric service, while providing direct boating access from Sarasota Bay to the Gulf of Mexico. Residents also enjoy opportunities for fishing, kayaking, paddleboarding, and other waterfront recreation. Located near Publix, St. Armands Circle, downtown Sarasota, shopping, dining, cultural attractions, botanical gardens, Anna Maria Island, and Sarasota-Bradenton International Airport, this extensively renovated villa offers an exceptional combination of updated interior finishes, outdoor living, boating amenities, and convenient access to the best of Longboat Key and the surrounding Sarasota area. Please see attached document for the full list of renovations & upgrades and full walkthrough video and virtual walkthrough. Not required to be 55 to purchase.

578 Spanish Drive S, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv. ⋅ 34228 Zip Code

Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Beach Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank flooring, new kitchen appliances, updated bathrooms with new vanities, and a bright, open floor plan designed for comfortable island living. Enjoy Sarasota Bay views from the living room, primary bedroom, and private rear patio. Step directly from your patio onto the beautifully landscaped lawn, where you can enjoy your morning coffee, watch boats and dolphins pass by, observe abundant coastal wildlife, and welcome beautiful Florida sunrises. The convenient ground-floor location offers effortless access and seamlessly blends indoor and outdoor living. Residents of this pet-friendly community enjoy the best of both worlds with deeded private Gulf beach access and outstanding amenities, including a heated pool, clubhouse, pickleball, tennis, fishing pier, kayak storage and launch, and assigned parking. Whether you enjoy boating, kayaking, fishing, shelling, or relaxing on the beach, this community offers the quintessential Longboat Key lifestyle. Ideally located near championship golf, waterfront dining, marinas, boutique shopping, St. Armand's Circle, and downtown Sarasota, this exceptional residence is perfect as a primary home, seasonal retreat, or investment opportunity. Don't miss this rare opportunity to own an updated, move-in-ready, bayside condominium with Sarasota Bay views, deeded private Gulf beach access, and the relaxed elegance of island living. EASY TO SHOW. SUPRA ON storeroom door across from front door.

5260 Gulf Of Mexico Drive Unit 413, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

Welcome to Longboat Harbour D-204, a beautifully maintained second-floor condominium in one of Longboat Key's most desirable gated waterfront communities. Ideally located in Building D—the closest building to the community's private Gulf beach access—this residence offers umatched convenience to the beach pavilion, showers, restrooms, and private beach lockers. Inside, you'll find a bright and comfortable floor plan featuring granite countertops, an in-unit washer and dryer, a spacious bedroom with a new impact window, and electric blinds. Additional highlights include a private storage locker, covered carport parking space, proximity to the elevator, a new roof, and all assessments fully paid. Longboat Harbour offers resort-style amenities including four heated swimming pools, a fitness center with sauna, tennis and pickleball courts, art studios, a woodworking shop, and a yacht club with a protected harbor. Located just miles from St. Armands, Lido Beach, Downtown Sarasota, Anna Maria Island, Homes Beach, and Bradenton Beach, this is the perfect opportunity to enjoy the best of Longboat Key waterfront and beach living.

4340 Falmouth Drive Unit D-204, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

If you are looking for a tastefully upgraded Longboat Key beach house, this is it! Relax in your completely renovated coastal-contemporary, stand-alone villa, with its front pond view, private rear patio and large yard space. The uncrowded, 11-mile Longboat Key beach is directly across Gulf of Mexico Drive via Spanish Main's private deeded access. Your spacious, light-filled home welcomes you with a charming entrance foyer, open living-dining room with built-in cabinets and a large kitchen-family room area with sliding doors to the rear yard. Your bright kitchen has an island, new appliances, quartz counters, and wood cabinets with lots of storage space. Important additional benefits include a new electric hot water tank, new hurricane rated doors and rear sliders, tile roof replaced in 2017, flat roof in 2024, impact windows in 2020 and 2024, and A/C in 2022. The primary bedroom has a walk-in closet and an en suite bath with a new walk-in shower and vanity. The guest bedroom has a view of the pond and double closets. The guest bathroom has a skylight and a new walk-in shower, vanity, linen and medicine cabinets. If you want to move right in or rent it, the attractive turn-key furnishings are negotiable. Outside, there is a large side storage area for bicycles and beach toys. The front porch offers a tranquil area to relax and view the large pond with its ducks, jumping fish, and pretty night lights. Walk, bike or drive to the heated community pool, patio area, and clubhouse adjacent to the deep water marina and kayak launch. If you are a boat person, slips can be rented, as available, for an extremely reasonable cost and there is easy access to Sarasota bay and the Intracoastal Waterway with no fixed bridges. Spanish Main Yacht Club is an over-55 community, conveniently located near several restaurants, Durante Park, community tennis, pickle-ball, dog park, fitness activities and St. Armands Circle shops and restaurants. Let me show you the lifestyle that this beautiful, unique villa has to offer.

524 Spanish Drive S Unit 125, Longboat Key

Start Your Search