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$500,000
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
$3,995,000
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
$949,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Discover this stunning, completely renovated interiors two-bedroom, two-bath home nestled in the Historic Longbeach Village on the quiet north end of Longboat key. More than just a home, this is a true coastal lifestyle. Perfectly positioned just a five minute walk to the largest public beach on Longboat Key. you'll enjoy effortless access to sugar-white sand, breathtaking Gulf sunsets, and endless days of beachside relaxation. Thoughtfully redesigned with upscale designer finishes throughout, this charming residence blends timeless Old Florida character with modern luxury. Terrazzo floors flow throughout the home, while the fully remodeled kitchen features premium cabinetry, quality appliances, and a functional layout that's perfect for everyday living or entertaining. Both bathrooms have been beautifully renovated with high-end finishes, including a luxurious primary bath with a large soaking tub, custom walk-in shower, and designer tile. No detail was overlooked and no expense was spared in this exceptional renovation. Leave the car behind and stroll to local favorites including Whitney's The Shore, and Mar Vista, all just minutes away. Ride your bike through the peaceful village, walk to the beach, or simply relax and enjoy the tranquil surroundings that make this neighborhood so special. Just over the bridge, Coquina Beach offers pristine shoreline, stunning Gulf Views, convenient concessions, and a popular farmers market, while Anna Maria Island provides an abundance of boutique shopping, waterfront dining, and laid-back island atmosphere. St. Armands Circle is only a short drive away with upscale shopping, restaurants, theater, marinas, and boat launches. Opportunities to own a fully renovated home in Historic Longbeach Village with this combination of location, walkability, and coastal charm are rare. Don't miss your chance to experience the serenity, beauty, and unmatched lifestyle of Longboat Key.

580 Linley Street, Longboat Key
$950,000
Conrad Beach SubDv. ⋅ 34228 Zip Code
"Create your ideal coastal retreat on the last available homesite in the peaceful and picturesque Conrad Beach enclave on Longboat Key. Just a 5-minute walk to the Gulf of Mexico and Whitney’s restaurant and a 2-minute drive to renowned restaurant Shore Longboat Key. This prime location offers easy access to pristine beaches and stunning sunsets. Conrad Beach is an award-winning neighborhood esteemed for its coastal charm and beautiful homes with low association fees covering yard maintenance, irrigation, and a community pool for a carefree lifestyle. Spanning 9,757 square feet, this homesite provides ample space to design your dream home and is conveniently located steps away from the community pool, offering a perfect retreat on sunny days. Longboat Key boasts some of Florida's most sought-after beaches, restaurants, tennis courts, and waterfront parks. With easy access to downtown Sarasota and St. Armands Circle, you'll have endless opportunities for recreation and entertainment. Don't miss this opportunity to create your coastal masterpiece in one of Florida's most desirable locations, where sun, sand, and sea await."

363 Firehouse Lane, Longboat Key
$325,000
1 Beds ⋅ 1 Baths ⋅ Neptune On Longboat Key SubDv. ⋅ 34228 Zip Code
Coastal Living on Longboat Key – Neptune Condominium Welcome to your island retreat at Neptune on Longboat Key, a charming boutique community just moments from the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect blend of comfort, style, and an unbeatable Longboat Key lifestyle. Step inside to discover a bright, open floor plan featuring luxury vinyl flooring, coastal-inspired décor, crown molding, and a tastefully renovated kitchen with cabinetry, updated appliances, quartz-look countertops, and a deep stainless sink. The spacious living and dining area flows effortlessly onto a screened lanai where you can relax with a morning coffee. The generous bedroom provides a peaceful retreat with abundant natural light, while the updated bath and thoughtful finishes create a move-in-ready coastal escape. Located on the desirable south end of Longboat Key, Neptune is a small boutique community known for its quiet atmosphere and convenient location. You're just a short stroll to the beach and only minutes from St. Armands Circle, where you'll enjoy world-class dining, shopping, and entertainment. Downtown Sarasota, cultural attractions, golf, boating, and marinas are also just a short drive away. Neptune is a small, low-density community with minimal common amenities, helping keep ownership simple while offering a peaceful island setting. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this turnkey-furnished condo offers an exceptional opportunity to own a piece of paradise on Longboat Key.

2850 Gulf Of Mexico Drive Unit 4, Longboat Key
$1,349,000
2 Beds ⋅ 2 Baths ⋅ Conrad Beach SubDv. ⋅ 34228 Zip Code
Located on the coveted west side of Gulf of Mexico Drive, just steps from the beach, 392 Firehouse offers the relaxed coastal lifestyle Longboat Key is known for. Nestled on a quiet cul-de-sac surrounded exclusively by charming Key West-style homes, this beautifully updated residence blends timeless island architecture with thoughtful modern enhancements. Residents also enjoy the community pool located directly across the street, along with the convenience of walking to three of Longbeach Village's beloved restaurants, making it easy to embrace the island lifestyle. Designed for effortless indoor-outdoor living, the home features an enlarged rear deck, fully equipped outdoor kitchen, outdoor shower, and a gas fire pit—creating the perfect setting for entertaining or unwinding after a day at the beach. Hurricane-impact sliding glass doors provide a seamless connection to the outdoor living spaces while filling the home with natural light. The home's curb appeal has been thoughtfully elevated with an updated exterior stucco finish, classic Bahama shutters, an artistic shell stone paver driveway, new professional landscaping, and landscape lighting that enhances the property after sunset. Inside, refinished hardwood floors bring warmth and character throughout, while sleek glass railings in the loft add a contemporary architectural element. The primary suite is enhanced with custom California Closet built-ins, providing exceptional organization and storage. Additional improvements include a new air conditioning system (2023), Tesla electric vehicle charging station, and an irrigation system. Offering an exceptional location just steps from the Gulf beaches, within one of Longboat Key's most charming coastal enclaves, this meticulously updated home embodies the very best of island living.

392 Firehouse Lane, Longboat Key
$400,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-13 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 80 x 23.5, and a usable beam of 19 feet and extra wide finger pier. This is a desired 'inside the T-head' slip location. 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, pickleball and golf facilities, fitness center, with spa and beach access. 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 75 feet. Beam depends on the vessel type and measure. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit R-13, Longboat Key
$479,500
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Club membership is NOT required and Owner Financing IS available for this rare 72' x 21' deep water boat slip on C-Dock at Longboat Key Moorings Marina, allowing for a 67' x 19' boat. Enjoy a premier deep-water, storm-protected marina location with direct access to Sarasota Bay, the ICW, and the Gulf. Longboat Key Moorings offers full-service amenities including dock crew, harbor concierge, 24-hour manned guard gate, cable TV, electricity, water, Wi-Fi, on-site fuel, pump-out service, and repair/maintenance services. Ideally located just minutes from St. Armands Circle, downtown Sarasota, Bradenton Beach, waterfront dining, shopping, and world-class boating. While membership to the Longboat Key Club is optional, it is not required to own this slip. A rare opportunity to secure premium waterfront access in one of Florida's most desirable boating communities.

2600 Harbourside Drive Unit C11, Longboat Key
$995,000
Coquina Beach SubDv. ⋅ 34228 Zip Code
It's all about location! Rare south end longboat key (Sarasota County) vacant lot situated steps from your own private deeded beach access. Spectacular water views from this oversized lot that's ready to build the home of your dreams. There is nothing else like this piece of property on the market. Close to some of the best dining, shopping, schools, entertainment and world class beaches! In the heart of the awesome Longboat Key one of the best islands in the United States there is truly nothing better then the amazing beach, beautiful blue waters and charming lifestyle of LBK!

521 Neptune Avenue, Longboat Key
$250,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
An exceptional 55-by-21-foot boat slip is ideally positioned in one of the most desirable locations within the Longboat Key Moorings Marina. Offering deep-water access with no bridges to Sarasota Bay and the Intracoastal Waterway, this premium slip provides effortless access to the Gulf and beyond. Longboat Key Moorings is a world-class marina offering individually owned slips, full-service concierge and maintenance services, and dockside electric, water and wireless internet. Residents enjoy the convenience of the adjacent Mediterranean-style village with waterfront dining, boutique shopping and nearby everyday conveniences, including Publix and CVS. A complimentary shuttle service to St. Armands Circle is also available. Membership to the Longboat Key Club is required, granting access to an exclusive private clubhouse featuring elegant gathering spaces, conference facilities, a television lounge and a variety of social events. Outdoor amenities include a private waterfront pool, grilling area, teak chaise lounges, dining tables and luxurious bathhouse facilities. Additional membership privileges include access to championship golf courses, tennis facilities, private beach access, a fitness center, a spa and wellness programs. Club members also enjoy reciprocity privileges with more than 700 yacht clubs nationwide. Experience luxury boating at one of Florida's premier marina destinations.

2600 Harbourside Drive Unit H06, Longboat Key
$39,500
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #2112 at The Boathouse on Longboat, rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6"Lx8'6"Wx7'2"H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2112, Longboat Key
$995,000
Long Beach SubDv. ⋅ 34228 Zip Code
Village of Longbeach — A Rare Canvas on Longboat Key's North End Tucked into the historic Village of Longbeach, this oversized 13,242 sq ft corner lot is a quiet invitation to build something lasting. Cleared and ready, it offers the rare chance to shape a custom coastal estate, a modern island retreat, or a thoughtful investment in one of Longboat Key's most storied neighborhoods. This is the island's tranquil north end — a beach-to-bay enclave where shell-strewn lanes wind beneath sea grape and gumbo limbo, and the rhythm of the day is set by tide charts and sunsets. Sarasota Bay lies steps in one direction, the sugar-sand shores of the Gulf in the other. Village life here is unhurried and genuine. Neighbors gather at the community dock for the long-standing "Yappy Hour" tradition, with bay access, fish cleaning station, and boat ramp just down the lane. Mornings might begin with coffee at a waterfront café; evenings unfold over dockside dinners at Mar Vista or Shore, a short stroll or golf cart ride from your door. Whitney's, boutique shops, fishing charters, and the free trolley to Anna Maria Island's Bridge Street are all within easy reach. Room enough for sweeping outdoor living, mature tropical plantings, and a home built around the way you want to live by the water — this is a quietly exceptional piece of old Florida, waiting for its next chapter.

591 Russell Street, Longboat Key
$5,995,000
4 Beds ⋅ 4 Baths ⋅ La Lenaire Isle SubDv. ⋅ 34228 Zip Code
Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades. The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island. Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets. The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests. The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise. Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment. Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle. Turn Key - Furnished.

7143 La Lenaire Drive, Longboat Key
$200,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Nicely manicured lawn fronts the area at the slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much as a resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina 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. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!

2600 Harbourside Drive Unit H-05, Longboat Key
$400,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
A 100 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, extra wide finger pier, and deep water. Huge turning radius, with easy access slip with the views to match the superb amenity package, Slip B-13 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 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. This is a Yacht Club slip. 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, 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. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 95 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.

2600 Harbourside Drive Unit B-13, Longboat Key
$18,500,000
2 Beds ⋅ 2 Baths ⋅ Robert Lennox Subdivision SubDv. ⋅ 34228 Zip Code
This house is a part of a 5.5 Property and will be sold together as one parcel. The house can be used as a guest house, caretaker home or removed for development.

6664 & 6660 & 6670 Gulf Of Mexico Drive, Longboat Key
$275,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
A favorite dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Easy access on and off the water to this H-dock slip. Club membership is not required. 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 marina 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. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!

2600 Harbourside Drive Unit H-04, Longboat Key
$18,500,000
Robert Lennox Subdivision SubDv. ⋅ 34228 Zip Code
Extremely Rare property in all of Florida. One of a kind.

6660 & 6664 & 6670 Gulf Of Mexico Drive, Longboat Key
$349,900
2 Beds ⋅ 2 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code
WELCOME TO PARADISE! This unit epitomizes the perfect beach home. When you step through the front door, you will know that you have entered “House Beautiful”. The blend of colors and furnishings will make you feel that you are home. This home features a nice-sized living room, totally upgraded separate kitchen and dining room, two bathrooms and two bedrooms. This home has 1,052 sq. ft. of living area. This home is located just steps from Sarasota Bay. There are limited views of Sarasota Bay from the Living Room, Dining Room, Kitchen and the second bedroom. It has a new Mini Split A/C, and hot water heater. The roof is vinyl and has a brand new elastomeric coating with a 5 year warranty. This unit also has new skirting and new edging on the roof soffits. Gulfshore of Longboat Key is located on a perfect parcel of land. It has it all – private access to a pristine sand beach on the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained and managed campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. Gulfshore does not permit rentals or pets and it is a 55+ community. Please call now for an appointment to view your future home and relax in paradise.

3710 Gulf Of Mexico Drive Unit G20, Longboat Key
$5,600,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Build your dream beachfront estate on nearly three-quarters of an acre on exclusive North Longboat Key. With 100 feet of private Gulf frontage, this rare homesite offers endless views of turquoise waters spectacular sunsets and direct access to powder sand just steps from your future doorstep. Set within a rising luxury enclave, this prime property is moments from the new St. Regis Resort and the Longboat Key Club, offering world-class golf, tennis, dining, and five-star amenities. Enjoy the charm of nearby Anna Maria Island and the upscale shopping and cultural experiences of St. Armands Circle. This is one of the last opportunities to create a custom beachfront retreat in one of the Gulf Coast’s most coveted locations

6441 Gulfside Road, Longboat Key
$5,985,000
Longboat Key Estates SubDv. ⋅ 34228 Zip Code
Currently under construction and masterfully designed for the ultimate waterfront lifestyle, this extraordinary canal-front estate in Longboat Key Estates offers an exceptional blend of luxury, comfort, and coastal elegance. Boasting 5 bedrooms, 7 bathrooms, and more than 4,500 square feet of thoughtfully crafted living space, the home features solid block construction and hurricane-impact windows, delivering both enduring quality and peace of mind. Designed to maximize seamless indoor-outdoor living, the southwest-facing pool and expansive entertaining areas capture spectacular sunset views over Sarasota Bay and toward the Gulf of Mexico. The elevated lanai is highlighted by detailed ceiling craftsmanship and a fully equipped outdoor kitchen, creating the perfect backdrop for entertaining guests year-round. For boating enthusiasts, the property includes a brand-new seawall and direct bay access, providing effortless navigation to the surrounding waterways. Residents also enjoy private beach access and exclusive HOA amenities, including a beachfront tiki hut for social gatherings and a bayside dock ideal for fishing, kayaking, swimming, or simply relaxing along the water’s edge. Nearby Bayfront Park offers additional recreational amenities including tennis courts, pickleball, walking trails, and a dog park. With construction already underway, buyers have the rare opportunity to personalize select finishes and tailor the residence to their individual style and vision. Ideally situated just minutes from St. Armands Circle, downtown Sarasota, and the world-renowned beaches of Longboat Key, this remarkable estate presents an unmatched opportunity to experience coastal living at its best.

530 Jessmyth Drive, Longboat Key
$6,495,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Rarely does an estate-sized Gulf-front lot of this stature become available on the northern end of Longboat Key. 6351 Gulf of Mexico Drive presents a truly exceptional 100-foot by 388-foot direct beachfront parcel — nearly 39,000 square feet of pristine Gulf of Mexico frontage. This distinguished property stands as one of the final remaining full beachfront estate-sized lots on Longboat Key, offering a rare and significant opportunity. Commanding sweeping, unobstructed views of the turquoise Gulf waters and the iconic white-sand shoreline, the site serves as a unique blank canvas for the creation of a bespoke oceanfront residence. The expansive and generously proportioned dimensions provide unparalleled design flexibility, allowing the accomplished buyer to fully realize a custom legacy property tailored to the highest standards of coastal elegance, privacy, and sophistication. Ideally situated, the property enjoys convenient proximity to the prestigious Longboat Key Club with its 45 holes of championship golf, tennis facilities, and fine dining. World-class restaurants are moments away, including The Shore, Whitney’s, Mar Vista, Euphemia Haye, and Lazy Lobster. Additionally, St. Armands Circle offers exceptional shopping and dining, while the fine and performing arts venues of downtown Sarasota are easily accessible. Positioned among notable residences yet defined by its substantial scale and immediate beach access, this parcel delivers the rare combination of exclusivity and architectural freedom. It is an offering for the discerning individual who has earned the right to create precisely what they envision — a timeless private sanctuary in one of Florida’s most prestigious coastal communities. Private showings by appointment.

6351 Gulf Of Mexico Drive, Longboat Key
$324,000
1 Beds ⋅ 1 Baths ⋅ Neptune On Longboat Key SubDv. ⋅ 34228 Zip Code
A renovated condo directly across from public beach access under $350,000. on Longboat Key? This is the one you've been looking for! Perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this location checks all the boxes. Walk across the street to watch sunset on the sand, then stroll to Publix, Bayfront Park's tennis & pickleball courts, the library, or one of the island’s cozy dining spots. Everything your guests—or you—could want is right at your doorstep. The unit features a bright, open living space with tile flooring, a spacious bedroom, walk-in closet and parking. The well-maintained community offers low HOA fees and a relaxing island vibe that keeps guests coming back. Don’t miss out on this rare opportunity to own on Longboat Key—whether you're investing in your future or your lifestyle.

2850 Gulf Of Mexico Drive Unit 5, Longboat Key
$760,000
Longboat Key SubDv. ⋅ 34228 Zip Code
Rare corner-lot opportunity in the historic and highly sought-after Longbeach Village on the north end of Longboat Key. Build your own tropical retreat with the potential for views of Sarasota Bay. Ideally located just a short stroll from beloved local favorites Mar Vista Dockside Restaurant & Pub and Shore Longboat Key. A public boat launch is only half a block away, and convenient public beach access awaits at the west end of Broadway Street. Even more opportunity awaits, as the adjacent lot is also available for purchase, creating the potential to combine both properties for a larger homesite, expanded outdoor living space, or a truly exceptional island compound. A prime location to create your dream coastal getaway.

720 Broadway Street, Longboat Key
$425,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. 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, 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. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 80 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.

2600 Harbourside Dr Unit B-08, Longboat Key
$425,000
Bay Isles SubDv. ⋅ 34228 Zip Code
A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. 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, 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. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 80 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.

2600 Harbourside Dr Unit B-06, Longboat Key
$2,500,000
Longboat Key Estates SubDv. ⋅ 34228 Zip Code
Build your waterfront residence and be perfectly positioned in one of Longboat Key’s most elegant neighborhoods- Longboat Key Estates where sunrise occurs over the Bay while sunset occurs over the Gulf. You will have both and each new day provides unique views. This build-ready lot offers 100 feet of deep-water canal frontage and 117 feet of depth from canal to street where you’ll enjoy direct access to Sarasota Bay. Load up the boat and cruise the bay, the Intracoastal Waterway, and the Gulf of Mexico, with popular waterfront restaurants along the way. Just over the bridge from the mainland, you’re moments from Sarasota —cultural venues, marinas, and everyday conveniences. A private deeded beach access lies just across Gulf of Mexico Drive, where a shady Tiki Hut welcomes you before taking a few short steps which lead to the gentle Gulf waters and sandy shoreline. The private Tiki Hut is often the venue for neighborhood parties and a frequent gathering spot for sunset seekers! This vacant lot on Rountree Drive presents a rare chance to enjoy both boating and beachside living in one extraordinary location. Your future dream home could capture panoramic bay and beach views, creating the perfect backdrop for unforgettable Florida sunsets. With no fixed bridges to the Gulf of Mexico except the new very high Ringling Bridge to the mainland, this is truly a boater’s paradise. Just steps away is Bayfront Park, a beautiful waterfront park overlooking Sarasota Bay. Amenities include picnic tables, tennis courts, lighted pickleball courts, basketball courts, shuffleboard, a kayak launch with rentals, a dog park with separate large- and small-dog areas, a playground, a multipurpose sports field, and a community center offering activities such as yoga and fitness programs. Located in the heart of Longboat Key, this ready-to-build homesite offers an unparalleled coastal lifestyle. Head north to Center Shops for local favorites such as the Lazy Lobster, Harry's Continental Kitchen, Mar Vista Dockside Restaurant & Pub, and the Shore Longboat Key. Travel south to St. Armand’s Circle for world-class dining, boutique shopping, and vibrant island charm, including Columbia Restaurant, Cha Cha Coconuts, The Daiquiri Deck, Dockside, Chart House, and Tommy Bahama’s Restaurant, among many other fine dining places. In summary, enjoy championship golf, boutique shopping, award-winning dining, and some of Florida’s most beautiful Gulf Coast beaches, all from your future home in Longboat Key Estates on Longboat Key!

581 Rountree Drive, Longboat Key
$70,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #1214 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8' 4" and an 8' 6" beam (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 1214, Longboat Key
$349,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
1 Block from private beach, completely remodeled 1100 sq ft modernized condo with open concept and lot of windows. Custom kitchen, completely gutted and new insulation and drywall. Custom glass-walls, 3 A/C zones. Villa is in 55 plus community with private beach and marina, clubhouse, shuffle board, in peaceful LongBoat Key.

541 Spanish Drive N, Longboat Key
$1,795,000
Emerald Harbor SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to own a Longboat Key waterfront home in the highly desired community of Emerald Harbor. This 3BR/2BA, 1,926-sf canal front home with pool sits on an oversized 100x155-ft lot along one of Longboat’s widest canals (~110 ft) offering deep-water boating access just a half mile to the Intracoastal Waterway. Private beach access with parking is less than half a mile away. The property experienced storm-related water damage in 2024 and is ready for renovation or a brand-new custom home build. Enjoy island living close to The St. Regis Longboat Key Resort, The Resort at Longboat Key Club, St. Armands Circle, and North Longboat Village favorites—Shore, Mar Vista, Whitney’s, and Lazy Lobster. Emerald Harbor Longboat Key home for sale combines boating, beach access, and the ultimate Florida lifestyle—an unbeatable fixer-upper Longboat Key canal-front opportunity in one of the island’s premier neighborhoods.

741 Old Compass Road, Longboat Key