One of the most popular communities provided by {{page_data.agentName}}

Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.

One of the most popular communities provided by Michael Graf

507

# of Listings

2

Avg # of Bedrooms

$867

Avg. $ / Sq.Ft.

$1,539,132

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

507 Properties Found. Page 19 of 34.

#A4667631

LONGBOAT KEY

4540 GULF OF MEXICO DRIVE 204

2 Beds

2 Baths

1,312 Sq.Ft.

$695,000

MLS#: A4667631

This desirable first-floor corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully refreshed with a neutral color palette and comes fully furnished, and is the lowest-priced unit in Grand Bay.

The kitchen shines with quartz countertops, full-height backsplash, double oven, new sink and plumbing fixtures, under-cabinet lighting, and stainless appliances. A convenient pass-through connects seamlessly to the living area for easy entertaining.

The primary suite offers floor-to-ceiling sliders opening to the oversized terrace, a luxurious ensuite bath with double vanity, glass-enclosed shower, jetted soaking tub, and custom walk-in closet. The private guest suite features its own bath, large walk-in closet, terrace access, and pocket doors for added privacy.

Additional highlights include two side-by-side under-building parking spaces near the elevator, and a private storage locker.
Grand Bay is a pet-friendly, guard-gated community offering resort-style living with semi-private elevators, a state-of-the-art fitness center, Har-Tru tennis courts, outdoor grills, and two sparkling pools. Residents also enjoy membership in the private Bay Isles Beach Club with deeded beach access, pavilion, restrooms, and gated parking.

LONGBOAT KEY

3070 GRAND BAY BOULEVARD 612

2 Beds

2 Baths

1,756 Sq.Ft.

$689,500

MLS#: A4671489

Experience breathtaking Sarasota Bay views from every room in this beautifully customized Windward Bay condominium. This coastal retreat offers a seamless blend of elegance and comfort, featuring designer upgrades and thoughtful touches throughout. The open-concept living area is centered around a stunning custom fireplace — a feature that adds warmth and character to the space.
Walls of windows fill the home with natural light and frame serene, panoramic bay and marina views, where dolphins, manatees, and pelicans glide across the water. The modern kitchen is equipped with stainless steel appliances and stylish finishes, while the spacious primary suite includes a generous walk-in closet and dressing area.
Step onto the enclosed lanai, tiled underfoot, and savor peaceful mornings watching the sunrise over the bay. Every detail has been carefully curated — from updated flooring and custom woodwork to contemporart fixtures and generous storage throughout.
Residents of pet friendly Windward Bay enjoy resort-style amenities including two heated pools, tennis and pickleball courts, fitness center, marinas with boat slips(fee and wait list), kayak storage, and deeded beach access just across the street. Perfectly located near Bayfront Park, shopping, dining, and St. Armands Circle, this home offers the best of Longboat Key living — tranquil, refined, and unmistakably coastal. Welcome home to the kind of life you don't just dream of-you live it here!

LONGBOAT KEY

4500 GULF OF MEXICO DR 305

2 Beds

2 Baths

1,312 Sq.Ft.

$689,000

MLS#: A4668880

Price reduced

#A4643486

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE Q2

2 Beds

2 Baths

1,248 Sq.Ft.

$684,900

MLS#: A4643486

The lowest Gulf Front condo at this low price -Don't Wait any longer!
Sought-After Beachfront Living at The Islander Club – Resort-Style Luxury on Longboat Key. Welcome to this beautifully updated 2-bedroom, 2-bath condo in the prestigious Islander Club, one of Longboat Key’s most desirable beachfront communities. Located on the 6th floor, this spacious residence spans over 40 feet along the south/southeast side, offering breathtaking Gulf views from the primary suite and the perfect setting for relaxed coastal living. Inside, you'll find new luxury engineered wood flooring throughout, fresh coastal-inspired paint, and updated lighting that complements the open floor plan. The bright and airy living space flows effortlessly from the kitchen to the main living area, while large impact windows in the primary bedroom bring in stunning natural light and uninterrupted Gulf views. The primary suite also features an ensuite bath, and there is a full-size washer and dryer in-unit along with extra storage off the living room for added convenience. The Islander Club offers an array of resort-style amenities including over 400 feet of private beach frontage, two fishing jetties, two Har-Tru tennis courts, a newly renovated community room with a full-size kitchen, billiards, table tennis, a library, fitness center, saunas, and on-site management and maintenance. A beautiful beachfront heated swimming pool and spa add to the luxury experience. Located just a short bike ride or drive to the Longboat Key Club, you’ll have easy access to exceptional dining, golf, tennis, and pickleball. The world-renowned shops and restaurants of St. Armands Circle are less than four miles away and easily reached by bike or car. Don’t miss the opportunity to enjoy the best of turnkey beachfront living and experience the ultimate in daily relaxation here on Longboat Key—just bring your flip flops and move right in.

LONGBOAT KEY

2295 GULF OF MEXICO DRIVE 64S

2 Beds

2 Baths

1,485 Sq.Ft.

$675,000

MLS#: A4655868

Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis is A Perfect Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space, this condo combines comfort, convenience, and a balcony help you unwind and enjoy the fresh coastal air. As a well-maintained residence (new HVAC 2025, hot water heater, stainless fridge), this home offers a welcoming, move-in ready atmosphere and provides a sanctuary where you can enjoy both peaceful living and the energy of Longboat Key's vibrant community. Why Live on Longboat Key? Longboat Key is renowned for its pristine beaches, relaxed atmosphere, and upscale lifestyle. With easy access to fine dining, shopping, cultural attractions, and outdoor recreation, it’s the ideal location for those seeking a laid-back coastal lifestyle, while still being close to the excitement of Sarasota. Whether you’re taking a morning stroll on the beach or enjoying the world-class amenities nearby, Longboat Key offers a unique blend of tranquility and activity. Club Longboat Beach & Tennis is more than just a place to live – it’s a destination where every day feels like a vacation. Enjoy direct access to the beautiful white sands of Longboat Key Beach, perfect for sunbathing, swimming, and watersports. The community offers resort-style amenities, including meticulously maintained tennis courts, a fitness center, a heated pool, and 24-hour security. Whether you’re looking to relax poolside or stay active with tennis or fitness, there’s something for everyone. Don’t miss out on the opportunity to own your slice of paradise.

LONGBOAT KEY

5055 GULF OF MEXICO DRIVE 435

2 Beds

2 Baths

1,484 Sq.Ft.

$675,000

MLS#: A4671314

Price reduced

Step back in time and experience the “Old Florida Lifestyle” in the heart of Longboat Key’s historic Longbeach Village! Tucked away on the northernmost end of the island, this rare property features two charming Key West–style beach cottages on one lot, surrounded by lush tropical landscaping for a truly private island retreat.

The main updated cottage offers a light-filled, open floor plan with 2 bedrooms, 2 bathrooms, a den, laundry room, and spacious living area. The kitchen was tastefully updated in 2021 with quartz countertops, hardwood cabinets, and newer appliances, complete with a breakfast bar for casual dining. Open the windows and let the coastal breeze fill your home, or step outside to the wooden deck and tiki bar—perfect for entertaining and enjoying evenings listening to the nearby Gulf waves.

Across the wooden overpass sits the guest cottage, a cozy retreat with 1 bedroom, 1 bathroom, full kitchen, living space, and a private porch. It even has its own access via the private alleyway, making it ideal for visitors or rental potential.

Additional updates include Hardie board siding (2021), appliances (2021), quartz countertops (2021), cabinets (2021), and A/C (2017), ensuring modern comfort while maintaining that laid-back island vibe.

With no HOA or deed restrictions, this property offers flexibility for personal use or investment. Best of all, it’s just steps from both the beach and the bay—enjoy Whitney Beach, two fishing docks, the community boat/kayak launch, and popular dining at Mar Vista and Shore.

LONGBOAT KEY

660 LINLEY STREET

3 Beds

3 Baths

1,564 Sq.Ft.

$675,000

MLS#: TB8425751

Discover the ideal blend of comfort, convenience and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key. Enjoy easy access to the gorgeous Gulf beach of Longboat Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active lifestyle. The main level of this townhome offers an open, eat-in kitchen with a breakfast bar that flows effortlessly into the inviting living room, complete with a wood-burning fireplace and large sliding doors leading to a screened lanai with stairs to the outdoors. A convenient half bath completes this level, making it ideal for entertaining. Upstairs, the primary suite features a spacious walk-in closet and a private en-suite bath with double sinks. A second bedroom, also with its full en-suite bath, provides comfort and privacy for guests. The laundry is conveniently on this upper level. On the garage level, you’ll find a large storage room and a bonus space, offering endless possibilities such as a home gym, hobby area or even a space for guests. Fairway Bay homeowners have access to the on-site clubhouse, where there are social activities, a community gym and Har-Tru tennis courts for residents only. Fairway Bay is in Bay Isles, where you have 24/7 gated security and deeded access to the beautiful and private Bay Isles Beach Club. Here you can enjoy gated parking, restrooms, beach chair and umbrella storage, an ice machine, refrigerator and microwave, the ideal place for barbecues, picnics, and sunset gatherings with family and friends. Furniture is included, making this an effortless move-in opportunity to start enjoying the Longboat Key lifestyle from day one. This home is in proximity to Longboat Key Club where you have 45 holes of golf, a world-class tennis center, pickleball courts and five private restaurants accessible to you with additional membership. It’s rare to find a home in Bay Isles offering this level of lifestyle, amenities and value. Don’t miss this opportunity to live your best life on Longboat Key and start making memories of a lifetime today.

LONGBOAT KEY

1912 HARBOURSIDE DRIVE 602

2 Beds

2 Baths

2,606 Sq.Ft.

$675,000

MLS#: A4668394

Experience true Bay-to-Gulf living with exclusive access to Sarasota Bay and the Longboat Key Beach through the private gated beach club just steps away! This beautifully fully renovated 2-bedroom and 2-bathroom top-floor end-unit condo in the highly desirable Longboat Harbour community combines modern updates, comfortable living spaces, and stunning water views from almost every room. Whether you’re looking for a full-time residence, a seasonal getaway, or a stylish vacation retreat, this condo is truly move-in ready and offers an incredible lifestyle on Longboat Key.

Step inside and you’ll immediately feel the sense of space and light. The open concept living and dining area flows effortlessly, making it perfect for both relaxing and entertaining. Elegant porcelain tile flooring runs throughout the condo, beautifully accented by refined crown molding and 6 inches baseboards. Large windows and glass sliders fill the space with natural light and showcase beautiful bay and canal views. The spacious private balcony lanai is enhanced with dual ceiling fans, creating the perfect spot to sip morning coffee, enjoy a good book, or unwind in the evening. This condo is being sold furnished, featuring carefully selected, high-quality pieces that perfectly complement the style, giving the space a model-like appearance. A detailed furniture list is available upon request. The updated kitchen is a chef’s dream, featuring Southern Stone custom cabinetry, quartz countertops, soft-close drawers, recessed LED lighting, and high-end stainless steel appliances including Fisher & Paykel and Bosch. The primary suite is a true retreat, offering direct balcony access, a custom-built closet, and a luxurious en-suite bathroom with quartz countertops, wood cabinetry, and a glass-enclosed walk-in shower. The guest bedroom also enjoys beautiful water views and has its own balcony access, a spacious closet, and a full bath nearby. This condo has been thoughtfully updated with IMPACT-RESISTANT PGT HURRICANE WINDOWS, a 28-foot LANAI with glass slider doors, a 2024 A/C SYSTEM, 2025 HOT WATER HEATER, stacked BOSCH WASHER & DRYER, NEW CEILING FANS throughout, a NEW ELECTRICAL PANEL WITH WHOLE-HOME SURGE PROTECTION, and STYLISH NEW INTERIOR DOORS. Every detail has been carefully considered to create a residence that is both elegant and functional. Living in Longboat Harbour means experiencing one of the most desirable communities on Longboat Key. Just steps away, you have access to the private gated beach club where you can relax on the sand, enjoy the Gulf breeze, and watch incredible sunsets every evening. The community also offers resort-style amenities designed to make every day feel like a vacation, including: 4 heated swimming pools, fully equipped fitness center, tennis and pickleball courts, fishing piers and kayak storage, boat slips available on a first come first served basis, vibrant clubhouse with social events and activities. Perfectly located on Longboat Key, you’ll be close to some of the area’s best dining, shopping, and entertainment options while still enjoying the peace and privacy of this gated waterfront community. Whether you’re looking for a serene retreat, a vacation property, or a full-time residence, this condo delivers everything you need to experience the very best of Florida’s Bay-to-Gulf lifestyle.

LONGBOAT KEY

4320 FALMOUTH DRIVE 301

2 Beds

2 Baths

1,316 Sq.Ft.

$650,000

MLS#: A4670725

Price reduced

#A4666980

LONGBOAT KEY

3320 GULF OF MEXICO DRIVE 207-C

2 Beds

2 Baths

1,187 Sq.Ft.

$649,999

MLS#: A4666980

Price reduced

One of a kind, never rented, ready for a new owner to put their touches on this opportunity! Unit has endless views. Come look, Being able to rent this unit, by the month, twelve times a year, that offers our beautiful GULF BEACH within seconds of the front door is incredible! Our third floor views are breathtaking, yet fully protected from the elements. Our Building is quiet, but close to BEACHPLACE amenities! Owners are motivated to sell and we can give you a complete tour when you visit. Also new HURRICANE Windows recently added. BONUS TWO PARKING SPACES,
ONE IN GARAGE,ONE OUTSIDE! BEST VALUE IN BEACHPLACE BY FAR> GO COMPARE!

LONGBOAT KEY

1065 GULF OF MEXICO DRIVE 302

2 Beds

2 Baths

1,392 Sq.Ft.

$649,000

MLS#: A4624142

LOCATION ALERT!!! Build your dream home on this 6,000 sq ft vacant residential lot. This spacious lot offers a creative, vast playground of architectural possibilities and also those famous and coveted gorgeous, Gulf sunsets and sunrises. You are located in the heart of The Village in Longboat Key, convenient walking distance to fabulous restaurants like The Shore, Mar Vista and Whitney's. The Gulf beaches are only a few blocks away to enjoy days relaxing on the beach. Build up and have panoramic views of the teal green water of the intercostal waterway. Don’t miss this great opportunity!

LONGBOAT KEY

6981 LOIS AVENUE

None Beds

None Baths

0.14 acres

$649,000

MLS#: A4648890

A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seaplace with no shared walls, offering unparalleled privacy and tranquility. Fully remodeled in 2019, the home features a designer kitchen with quartz countertops, custom cabinetry and premium appliances, seamlessly complemented by elegant soft grey laminate hardwood flooring throughout. A spacious lanai spans the length of the residence, filling the interior with natural light and picturesque garden views. Significant recent upgrades include a new air-conditioning system (2020) with added UV filtration (2024), hurricane-rated sliding doors in the primary suite and living room (2025) and a water heater (2020), all with transferable warranties. Additional highlights include floor-to-ceiling remote-controlled blinds, an in-unit full-size washer and dryer, and a reserved parking space. Seaplace offers a wealth of resort-style amenities, including two swimming pools, two hot tubs, a kiddie pool, Har-Tru tennis courts, a fitness center, a newly renovated clubhouse, beachfront grilling areas and private beach access. The 24-hour guard-gated community ensures security and exclusivity. Ideally just minutes from St. Armands Circle, this prime location provides convenient access to world-class dining, luxury shopping and Sarasota’s renowned cultural attractions. Whether you're seeking a full-time coastal residence, a seasonal getaway or a high-demand investment opportunity, this penthouse represents the finest in Longboat Key living. Schedule your private showing today!

LONGBOAT KEY

1935 GULF OF MEXICO DRIVE G7-402

2 Beds

2 Baths

1,068 Sq.Ft.

$649,000

MLS#: A4667002

#A4659070

LONGBOAT KEY

4350 CHATHAM DRIVE E307

2 Beds

2 Baths

1,072 Sq.Ft.

$649,000

MLS#: A4659070

Price reduced

Exceptional full Bay views and incredible value! This fully furnished 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast-bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights include hurricane-rated windows and doors, in-unit laundry, a 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two tennis/pickleball courts, a clubhouse, kayak storage and launch, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE E2

2 Beds

2 Baths

1,248 Sq.Ft.

$649,000

MLS#: A4667654

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