Longboat Key Homes under $500,000

Longboat Key Homes under $500,000

Welcome to Longboat Key, Florida, a picturesque paradise where the sun kisses the azure waters of the Gulf of Mexico. Renowned for its stunning beaches, vibrant sunsets, and lush tropical landscapes, Longboat Key is a haven for those seeking a tranquil lifestyle infused with coastal charm. This barrier island boasts a unique blend of luxury and laid-back living, making it an ideal destination for families, retirees, and everyone in between.

One of the most appealing aspects of Longboat Key is its diverse real estate market, which includes attractive options for homebuyers looking for properties under $500,000. Here, you can find charming condos, cozy beach cottages, and well-maintained villas that offer a slice of paradise without breaking the bank. These homes provide easy access to pristine beaches, delightful dining, and an array of recreational activities, from kayaking and paddleboarding to golfing and biking along scenic paths.

The community is known for its friendly atmosphere and welcoming spirit, making it easy to forge connections with neighbors and enjoy a sense of belonging. With a variety of local shops, restaurants, and art galleries, Longboat Key is not just a place to live; it’s a lifestyle.

Whether you’re looking for a vacation retreat or a permanent residence, Longboat Key’s real estate market offers something for everyone. Discover your dream home in this coastal gem and embrace the idyllic Florida lifestyle today!

Newest Longboat Key Homes under $500,000

2600 Harbourside Drive Unit C3, Longboat Key
$275,000
1 Beds ⋅ 1 Baths ⋅ Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Experience the luxury boating lifestyle on Longboat Key. This 62' x 21' deeded boat slip is positioned on serene deep water at Longboat Key Club Moorings, a full-service, world-class Marina with every desirable amenity. This NON-COVENANT slip does not require the new owner to join the Longboat Key Club although club membership is an available option. C Dock is especially desirable due to the unique design of the finger piers which allow boarding on most vessels without the need for an additional boarding ladder. Owners of boat slips have the option to join the Bay Isles Beach Club for a small annual fee. This is a deeded live aboard slip, a rarity in today’s market, with great rental potential making this a unique opportunity for investors and boaters alike. Currently rented with income in place until a new owner is ready to occupy.

2600 Harbourside Drive Unit C3, Longboat Key
408 Gulf Of Mexico Drive Unit 2207, Longboat Key
$49,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #2207 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 28 feet in length, with a maximum height of 7'8" 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 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 2207, Longboat Key
408 Gulf Of Mexico Drive Unit 1206, Longboat Key
$65,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #1206 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 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 1206, Longboat Key
408 Gulf Of Mexico Drive Unit 2114, Longboat Key
$39,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Welcome to Slip #2114 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 23.5 feet in length, with a maximum height of 7'2" 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 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 2114, Longboat Key
2800 Harbourside Drive Unit E-21, Longboat Key
$385,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. 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, 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 & 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. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-21, Longboat Key
3453 Gulf Of Mexico Drive Unit 237, Longboat Key
$495,000
1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code
This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

3453 Gulf Of Mexico Drive Unit 237, Longboat Key
96 Twin Shores Boulevard, Longboat Key
$399,000
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. Beautifully located 55+ Community. Own the land you live on in Longboat Key. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 6 feet up, 2-bedroom, 2 bath, open floorplan home. 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 future 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 pickle ball, 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!!! Hurry, Paradise Awaits!

96 Twin Shores Boulevard, Longboat Key
3453 Gulf Of Mexico Drive Unit 242, Longboat Key
$489,900
1 Beds ⋅ 1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code
Sea Horse is a resort community on the Gulf of Longboat Key and this unit offers a large balcony with sweeping views of the Gulf, beach, pool and epic Longboat Key sunsets. Unit 242 is a deluxe 1 bedroom with an open kitchen, dining room and living for guests to gather and a private bedroom with ensuite. The living room and bedroom share the balcony. As a resort, the on-site management office handles your rentals, maintenance, and guest needs. Parking is limited to one car for this unit. This is a quality investment property and rental projections are available upon request, but also consider this your little oasis to visit, enjoy and when you leave it's taken care of.

3453 Gulf Of Mexico Drive Unit 242, Longboat Key
2800 Harbourside Drive Drive Unit M-10, Longboat Key
$289,000
Bay Isles SubDv. ⋅ 34228 Zip Code
A 58 ft. x 20 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. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

2800 Harbourside Drive Drive Unit M-10, Longboat Key
4370 Chatham Drive Unit 304, Longboat Key
$425,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
MAJOR $74,000 PRICE REDUCTION, don't miss this newly priced opportunity. Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on the top-floor in Building G at Longboat Harbour. Featuring 2 bedrooms and 2 bathrooms, this move-in-ready residence offers peaceful canal views, thoughtful updates, and exclusive access to a private, gated beach club on the Longboat Key Gulf Beach, just steps away. Building G also offers a special community feature: a dedicated bump-out area designed for residents’ outdoor gatherings and entertaining. This exclusive feature is available to only two buildings within Longboat Harbour, and Building G is one of them. The bright and inviting interior features a carpet-free design with luxury vinyl plank flooring throughout with tiled bathrooms. New lighting fixtures, custom window treatments and ceiling fans add a fresh, updated touch, while the kitchen is appointed with granite countertops and a stylish backsplash. The updated primary bathroom provides additional comfort and modern appeal with custom vanity and cabinet storage. A new HVAC system installed in 2025 offers added peace of mind. Step outside to the spacious screened lanai, where beautiful canal views create a relaxing backdrop for everyday living, and on those lucky days, you may even catch a glimpse of manatees swimming peacefully through the water. Enhanced by a ceiling fan, this private outdoor space is perfect for enjoying morning coffee, reading a good book, entertaining guests, or unwinding at the end of the day. The condominium is being sold furnished with carefully selected pieces that complement the home’s coastal style and create a warm, comfortable atmosphere. Whether you are searching for a full-time residence, seasonal getaway, or coastal vacation retreat, this property is ready to enjoy from the moment you arrive. Longboat Harbour at Longboat Key offers an exceptional waterfront lifestyle with access to both Sarasota Bay and the beautiful Longboat Key Beach. The community’s private, gated beach club provides a convenient place to relax on the sand, enjoy the Gulf breeze, and take in beautiful Florida sunsets. Residents also enjoy an impressive selection of resort-style amenities, including four heated swimming pools, a fully equipped fitness center, tennis and pickleball courts, fishing piers, kayak & bicycle storage, and boat slips available on a first-come, first-served basis. The community clubhouse/banquet hall offers social events and activities, providing plenty of opportunities to meet neighbors and enjoy an active coastal lifestyle. Ideally situated on Longboat Key, this gated waterfront community offers convenient access to some of the area’s best dining, shopping, and entertainment while maintaining a peaceful and private setting. Whether used as a serene retreat, vacation property, or full-time residence, this furnished condominium provides everything needed to experience the very best of Longboat Key’s Bay-to-Gulf lifestyle. Schedule your private showing or request your virtual tour today, don't miss out this GEM on Longboat Key.

4370 Chatham Drive Unit 304, Longboat Key
3802 Gulf Of Mexico Drive Unit A203, Longboat Key
$399,000
2 Beds ⋅ 2 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code
Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

3802 Gulf Of Mexico Drive Unit A203, Longboat Key
3453 Gulf Of Mexico Drive Unit 200, Longboat Key
$390,000
1 Beds ⋅ 1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code
TURNKEY BEACHFRONT LIVING WITH EXCEPTIONAL RENTAL FLEXIBILITY ON LONGBOAT KEY! Located at Sea Horse Beach Resort, this spacious 1-bedroom, 1-bath condominium offers 876 square feet and an opportunity to enjoy the island lifestyle while taking advantage of short-term rental potential. With rentals managed on-site and minimum stays of just 7 days during season and 3 days throughout the remainder of the year, this property offers flexibility for buyers seeking a vacation retreat with income-producing potential. Inside, the bright and open floor plan features cathedral ceilings, luxury vinyl flooring, and comfortable living and dining spaces that make it easy to settle into island life. The kitchen opens to the main living area, while the loft-style bedroom creates a private retreat above. Step outside, and the reason to own on Longboat Key becomes clear. Sea Horse Beach Resort is located directly along the Gulf, offering a beachfront pool, expansive Gulf views, and the sand and water just steps away. Whether you're searching for your own Longboat Key getaway, a seasonal escape, or a property with short-term rental opportunities, Unit 200 offers a compelling combination of location, flexibility, and laid-back Gulf Coast living.

3453 Gulf Of Mexico Drive Unit 200, Longboat Key
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