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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
511
# of Listings
2
Avg # of Bedrooms
$856
Avg. $ / Sq.Ft.
$1,506,912
Med. List Price

Browse Long Boat Key Real Estate Listings

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511 Properties Found. Page 26 of 35.

The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully designed interiors featuring soaring ceilings and expansive floor-to-ceiling sliding glass doors that wrap around the living, dining, and kitchen spaces — framing breathtaking sunrise and sunset views. The gourmet kitchen is a chef’s dream, appointed with Wolf and Sub-Zero appliances, including a six-burner gas cooktop, double ovens, and a paneled side-by-side refrigerator and freezer. The elegant owner’s suite offers a private sanctuary with a spacious walk-in closet featuring custom wardrobe cabinetry, a frameless walk-in shower, and a secluded water closet. A private elevator with keyless entry provides direct access from your private two-car garage into your residence for ultimate convenience and privacy. Nestled within 17 acres of pristine beachfront, The Residences are part of Sarasota’s most exclusive resort enclave. Enjoy unparalleled amenities, including access to St. Regis Butler and Concierge services, a residents-only pool and spa, a private clubhouse, a state-of-the-art fitness center, and beachside cabanas. Just steps away, immerse yourself in the world-class offerings of The St. Regis Longboat Key Resort — from the pristine private beach and family-friendly pools to the unique saltwater lagoon wildlife experience, home to resident Aldabra tortoises. Indulge in rejuvenation at the oceanfront spa featuring vitality pools or delight in one of the resort’s vibrant, chef-driven dining destinations. Experience coastal luxury redefined — The Residences at The St. Regis Longboat Key invite you to live where timeless elegance meets the serenity of the sea. Inquire about 6 and 9 month pricing.
#A4671506

LONGBOAT KEY

1581 GULF OF MEXICO DRIVE 307

1 Beds

1 Baths

1,721 Sq.Ft.

$25,000

MLS#: A4671506

Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat. The expansive living room is thoughtfully furnished with a plush sectional, creating the perfect place to unwind after a day of feeding stingrays at Under The Sea or soaking up the Florida sunshine by the residence pool or the pristine Gulf-front beach. The chef’s kitchen is a dream come true, outfitted with top-of-the-line appliances, sleek cabinetry, and a spacious island with three barstools—ideal for casual bites or entertaining in style. Step outside to your private patio, an inviting space for morning coffee, or evening cocktails. With a built-in outdoor grill and outdoor seating, it's perfect for gatherings with family and friends. The luxurious primary suite offers a king-size bed, a smart TV, and direct access to the patio. The attached primary bathroom is a spa-like sanctuary, featuring a dual vanity, indulgent soaking tub, expansive walk-in shower, and a high-end Toto toilet for ultimate comfort. The second bathroom is equally refined, offering a spacious walk-in shower and elegant vanity, providing a seamless experience for guests. This residence has everything you need—and more—to truly relax, unwind, and enjoy a life of luxury in one of Longboat Key’s most prestigious addresses. Immerse yourself in unparalleled relaxation and luxury at The St. Regis Longboat Key Resort, where every detail has been thoughtfully curated to deliver an extraordinary experience. Nestled among soaring palms and lush tropical landscaping, the resort's centerpiece—known as “The Pools”—offers a serene escape with a variety of sparkling swimming pools, plush loungers, and private cabanas designed for ultimate comfort and seclusion. Just moments from your doorstep, the private beach invites you to unwind with attentive service and uninterrupted views of the Gulf of Mexico. Additional world-class amenities include the indulgent St. Regis Spa, a state-of-the-art Fitness Center, and an engaging Children’s Club—ensuring that every member of your party experiences the very best of coastal luxury. The residences enjoy their own private area, thoughtfully separated from the resort for added exclusivity. Here, a serene pool and spa overlook the breathtaking Gulf of Mexico, offering a peaceful retreat just steps from your door. The outdoor space features grills and seating areas—perfect for hosting gatherings with friends and loved ones. Stay active in the state-of-the-art fitness center, fully equipped with everything you need for an energizing workout. You'll also find convenient touches like a resident-only coffee station and more, designed to elevate your everyday living experience. Please Note: Upon arrival, guests must check in at the concierge desk in order to access their unit. House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.  While on property, please note that all spa treatments and dining experiences must be paid for at the time of service. Charging services to the unit is not permitted.
#A4651194

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 315

1 Beds

2 Baths

1,600 Sq.Ft.

$25,000

MLS#: A4651194

Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size beds. There is an inviting heated pool and hot tub plus an outdoor area for family and friends to enjoy. The kitchen with all new appliances and soft close cabinets is a cooks delight. The comfortable main sitting area looks out over the pool and wide canal. If you're into boating or fishing, there's a brand new boat dock and a boat lift for your use. The community has a private beach access directly across the street. Emerald Harbor is a quaint neighborhood comprised of 3 quiet streets. Enjoy deeded access to the beautiful beach and warm GULF waters on the shores of LONGBOAT KEY. LUXURY, LONGBOAT KEY, VACATION RENTAL, SARASOTA, GULF OF MEXICO.
#A4670519

LONGBOAT KEY

690 OLD COMPASS ROAD

3 Beds

3 Baths

3,230 Sq.Ft.

$25,000

MLS#: A4670519

This EXQUISITE 3 bedroom - 3 ½ bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14’ ceiling’s perimeter creating a dramatic living space. The entire condo has been renovated incorporating the latest in design, trends and materials. A few of the highlights are: custom “barn doors”, custom kitchen cabinetry with floor to ceiling pantry space, state of the art appliances and a quartz countertop, a wine fridge and custom bar space, new recessed lighting and spectacular light fixtures, master suite complete with custom closets, king size bed and a breathtaking bathroom, a guest bedroom with an en suite bath. All of this with outstanding, breathtaking views of the Gulf, Bay and Golf Course. You won’t find another unit like this on LONGBOAT KEY. Schedule an appointment to visit today. LUXURY, GULF OF MEXICO, SARASOTA RENTALS, LONGBOAT KEY.
#A4504509

LONGBOAT KEY

455 LONGBOAT CLUB ROAD PH1

3 Beds

3 Baths

2,780 Sq.Ft.

$25,000

MLS#: A4504509

Experience Gulf-front living at its finest on the pristine shores of Longboat Key. This exceptional 4-bedroom, 4-bathroom coastal retreat spans nearly 3,000 sq. ft. and sits on over half an acre of direct beachfront property. Thoughtfully furnished with a mix of modern and timeless design, this two-story residence offers stunning water views from almost every room. ( Available December 1st, 3 Month Minimum) Step straight onto the sand from your back door and enjoy the convenience of two Gulf-front pools, expansive pavered decks, and beautifully landscaped grounds. Inside, you’ll find state-of-the-art kitchens equipped with premium appliances including a Wolf gas range, Sub-Zero refrigerator, and Miele dishwasher. The open living and dining areas feature elegant fireplaces, engineered hardwood floors, and impact-rated windows and doors for comfort and peace of mind. The home offers main-level guest suites and upper-level Gulf-front primary suites complete with spa-inspired marble bathrooms and dual walk-in closets. Additional amenities include two two-car garages, storm shutters, and private walkways leading to your own stretch of beach. Perfectly located just minutes from the Longboat Key Club, St. Armands Circle, and Downtown Sarasota, this home provides easy access to world-class dining, shopping, golf, and tennis. Whether you’re seeking a luxury beachfront escape or a spacious multi-generational getaway, this rare Gulf-front rental delivers the ultimate coastal lifestyle.
#A4673823

LONGBOAT KEY

4473 GULF OF MEXICO DRIVE 4473

4 Beds

4 Baths

2,943 Sq.Ft.

$20,000

MLS#: A4673823

Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf. The primary suite includes a private balcony, a walk-in closet, and a spa-style bath. The kitchen is stocked with modern stainless steel appliances and features gorgeous counters, a curved island, and extensive storage with full cabinetry all while enjoying the breath taking views. Step outside to enjoy a private pool surrounded by generous patio space, perfect for lounging or dining outdoors. From the backyard, you’ll have direct access to the beach, making it easy to watch the sunset or stroll along the shoreline every night. The home also includes a spacious 4-car attached garage. SMALL dogs are allowed; cats are NOT permitted.
#A4666928

LONGBOAT KEY

5801 GULF OF MEXICO DRIVE

4 Beds

4 Baths

4,236 Sq.Ft.

$19,975

MLS#: A4666928

The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero appliances, a six-burner gas cooktop, double ovens, and a panel-ready side-by-side refrigerator/freezer. The owner's suite includes a spacious walk-in closet with custom cabinetry, a frameless walk-in shower, and a private water closet. A semi-private elevator with keyless entry provides direct access from the private garage. Residents enjoy access to The St. Regis Resort's legendary Butler and Concierge services, a private clubhouse, resident-only pool and spa, a state-of-the-art fitness center, and beachside cabanas. Just steps away, the resort offers a private Gulf-front beach, multiple pools with cabanas, a family-friendly waterway, an exclusive saltwater lagoon with Aldabra tortoises, and a world-class oceanfront spa. Experience the pinnacle of coastal elegance at The Residences at The St. Regis Longboat Key.
#A4644494

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 313

2 Beds

2 Baths

2,143 Sq.Ft.

$18,000

MLS#: A4644494

Experience refined coastal luxury in this exclusive beachfront residence, available for the 2026 season. Gulf views greet you in nearly every room, with designer finishes, a chef’s kitchen, spa-style primary suite, and private beach access. With bespoke interiors and elevated design, this privately released residence redefines coastal sophistication. Longboat Key Towers offers amenities including a heated beachfront pool, fitness center, guest suites, sauna, and private event space. One-of-a-kind. One Winter to remember. Available January through March of 2026.
#A4661151

LONGBOAT KEY

601 LONGBOAT CLUB ROAD 404S

2 Beds

2 Baths

1,560 Sq.Ft.

$15,500

MLS#: A4661151

LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room combination with floor to ceiling sliding glass doors to enjoy the breathtaking waters of the Gulf of Mexico, brand new wood tile flooring and fresh paint throughout. The large kitchen has solid stone counters, wood cabinets, offers plenty of space for cooking/food preparing and a closet pantry. The primary bedroom has a king sized bed, amazing views of the Gulf of Mexico and walk out access to a private terrace, a walk in custom closet and an on suite bathroom with a garden tub, stall shower and double sinks. The first guest bedroom has a view of the Gulf of Mexico, a king sized bed, a custom walk in closet and on suite bathroom with a walk in shower. The second guest bedroom has two queen sized beds and a custom walk in closet. The guest bathroom has a stall shower. The condo has a laundry closet with full sized washer and dryer. Two parking spaces come with the rental of which one is covered and one is in the garage. The Player Club is abound with amenities which include 24 hour guard gated entry, private beach access with cabanas, putting green, heated salt water community pool and hydro therapy spa, BBQ grills, fire pits, 4 Har-Tru tennis courts, fitness center and a large clubhouse with a rooftop deck. No pets allowed. Three month minimum rentals due to the Association. CALL TODAY. This is not one to miss and will not last long!! THE KITCHEN IS BEING REMODELED SUMMER 2025 SO NEW PICTURES TO COME.
#A4609098

LONGBOAT KEY

1465 GULF OF MEXICO DRIVE 504

3 Beds

3 Baths

1,710 Sq.Ft.

$15,000

MLS#: A4609098

Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a gourmet kitchen featuring quartz countertops, a breakfast bar, custom glass front cabinets, a glass front refrigerator and custom light fixtures. The flooring is luxury vinyl throughout, the main living area has a wet bar, electric fireplace, flat screen TV and lots of comfortable seating. The primary bedroom has a king bed, wall-mounted flat screen TV, built-in vanity and two walk-in closets, and the primary bath has a spacious shower with built-in seating and dual sinks. The guest bedroom and bath can be closed off for privacy and have a queen bed, wall-mounted flat screen TV and gorgeous water views! The Promenade is an upscale community with recently updated amenities, they have two areas to grill, a wonderful pool and spa, fitness, tennis and private beach access. The property is just five minutes to Publix, CVS and St Armands Circle.
#A4658115

LONGBOAT KEY

1211 GULF OF MEXICO DRIVE 1005

2 Beds

2 Baths

2,135 Sq.Ft.

$15,000

MLS#: A4658115

Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this turn-key furnished 4-bedroom, 2.5-bath home in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station (all 2022–2023). Completely remodeled to the studs recently, this home blends elegant design and high-end engineering: new roof, plumbing, electrical, and PGT hurricane-impact sliding doors and windows throughout. The flowing open-concept floor plan extends to a resort-style outdoor area through retractable glass walls, revealing a heated pool, travertine decking, and inspiring partial Bay views of Sarasota Bay and the Ca’d’Zan. The showpiece chef’s kitchen sets the standard for luxury with custom Devittori cabinetry, level 5 leathered granite, and a massive 11’x5’ island crafted from a single granite slab. Outfitted with premium Sub-Zero and Wolf appliances, including a 60” range with double ovens, six burners, dual griddles, a pot filler, Sub-Zero wine fridge, refrigerator drawers, and designer hood. It’s also a fully integrated Smart Home—control lighting, fans, blinds, and even the kitchen faucet with voice commands or an app. Enjoy deeded private beach access, or join the nearby Longboat Key Club for world-class golf, tennis, and dining—all minutes from St. Armand's Circle and Downtown Sarasota. Live the Longboat Key waterfront lifestyle—where boating, beach, and luxury converge in one extraordinary home.
#A4669549

LONGBOAT KEY

595 BOWSPRIT LANE

4 Beds

2 Baths

2,550 Sq.Ft.

$14,500

MLS#: A4669549

Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances and a gas range. The private, fully fenced backyard offers a heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing sound of swaying palms. Serene Village location with no public parking ensures exceptional peace and privacy. Ample boat/RV parking on site and deeded bay access steps away. Walk to Mar Vista Dockside Restaurant & Pub; minutes by car or bicycle to St. Armands Circle and Lido Beach. Offered fully furnished for a minimum 28-day rental period. Two king suites with dual closets each plus queen sleeper sofa in Main House. Ideal snowbird retreat or extended-stay executive residence. Available now.
#A4673262

LONGBOAT KEY

701 BROADWAY STREET

2 Beds

2 Baths

1,650 Sq.Ft.

$14,400

MLS#: A4673262

DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale kitchen, and tranquil living area. The primary King suite features an elegant walk-in shower and double vanity, along with a guest closet that will provide everything you need for a peaceful night’s sleep. A spacious queen guest bedroom next to the second bathroom, and a cozy third bedroom designed around a queen bed with a twin bunk perfect for additional guests. This unit in a hard to find 8-unit complex with breathtaking Gulf views, a private beach access located on the North end gives you the best of what the Key has to offer, privacy, amazing restaurants throughout Longboat, relaxing beach walks, unforgettable sunsets, a short stroll to many nearby restaurants and is centrally located; only 8 miles north from the renowned St. Armond’s Circle known for its outstanding restaurants and shopping scene, and 8 miles south of Anna Maria Island, known for its good eats, live music and fun atmosphere. Call for rates and availability.
#A4609144

LONGBOAT KEY

5611 GULF OF MEXICO DRIVE 1

3 Beds

2 Baths

1,675 Sq.Ft.

$14,000

MLS#: A4609144

Price reduced
Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost 2500 Sq. Ft. of Interior Living, The Home Offers 4 Bedrooms, 3 Full Washrooms, 2 Balconies and Exquisite Finishes Throughout. Tropical and Lush Landscaping With Gorgeous Canal & Bay Views. An Outdoor Kitchen & Seating Area With A Sparkling Pool Overlooking The Canal. Bright Open Concept Floor Plan Features A Gourmet Kitchen including Large Island and High End Appliances. Located just three lots from the Canal Opening to the Intracoastal Waterway, this property provides quick and easy access to Sarasota Bay, the Intracoastal and the Gulf of Mexico. Close To Restaurants, Shops, Parks and only minutes From St. Armands Circle, Lido Beach, Anna Maria Island, Bradenton Beach and Downtown Sarasota.
#A4660191

LONGBOAT KEY

830 TARAWITT DRIVE

4 Beds

3 Baths

2,447 Sq.Ft.

$14,000

MLS#: A4660191

Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the stylish seating, dining! The master suite offers wonderful Gulf views and access to the open patio, a king bed, flat screen TV, and walk-in closet. The master bath has dual sinks, soaking tub and an oversize shower. The guest bedroom offers two twin beds, flat screen TV, and views of the lushly landscaped grounds and views of the bay. In unit washer and dryer. This is one of the most sought-after buildings on Longboat Key, this well managed community was recently renovated with elegantly redecorated lobby and corridors, along with two social rooms, the Sunrise and Sunset rooms. There are Men's and Women's workout rooms, four Har-Tru tennis courts, two outdoor gazebos with gas grills and seating, a gorgeous gulf side heated resort style pool and spa, all surrounded by meticulously maintained grounds. Take the walkway to the sparkling sands of the private beach where there are plenty of chairs and chaises to relax and restore! The community offers 24/7 security and concierge services, and on-site management. Wake up, and fall asleep to, the sound of the waves gently lapping the shore. Welcome to Paradise!
#A4604126

LONGBOAT KEY

1211 GULF OF MEXICO DRIVE 405

2 Beds

2 Baths

1,598 Sq.Ft.

$14,000

MLS#: A4604126

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