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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

414

# of Listings

2

Avg # of Bedrooms

$791

Avg. $ / Sq.Ft.

$1,312,840

Med. List Price

Browse Long Boat Key Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

87 Properties Found. Page 2 of 6.

Discover this exquisitely renovated condo with high-impact windows and sliders that lives like a single-family home! This fully furnished 3-bedroom, 2-bath home in the friendly “Harbour Oaks” section of the prestigious Bay Isles community on Longboat Key comes with a private 2 car garage. With just under 2,000 square feet of living space, this residence perfectly combines luxury, comfort, and convenience. This home has been meticulously designed with high-end finishes by an interior designer, offering a sophisticated aesthetic throughout, featuring custom wood paneling, recessed lighting, engineered wood floors, Stark wool carpet in the primary bedroom, and custom window treatments. The 2020 upgraded kitchen features premium stainless-steel appliances and an induction range. Additional thoughtful design elements include cove lighting in the dining room and a wood-burning fireplace with custom Carrera Marble surround. The lanai with a motorized no-see-um bug screen overlooks the Longboat Key Club Harbourside Golf Course, providing breathtaking and comfortable sunset views framed by beautiful trees and lush greenery. For safety, durability and financial peace of mind, this gorgeous second floor residence features recently upgraded high-impact sliders and windows, plus community-wide new roofing and siding. Located in the gated Bay Isles community with 24/7 security, this home is within walking or biking distance to the private and newly renovated Bay Isles Beach Club, the Longboat Key Club Moorings Marina and Portofino restaurant, the Longboat Key Club Pickleball and Tennis Courts, Publix, CVS, as well as to the new Longboat Key St. Regis, which offers exceptional dining options and the vibrant St. Regis Monkey Bar, now open to the public. This remarkable turn-key property with a beautiful community pool and spa offers a rare opportunity to embrace the unparalleled Longboat Key lifestyle. Don’t miss the chance to make it your own.

LONGBOAT KEY

2195 HARBOURSIDE DRIVE 404

3 Beds

2 Baths

2,600 Sq.Ft.

$949,000

MLS#: A4635715

Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout.

Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.

LONGBOAT KEY

5924 GULF OF MEXICO DRIVE

2 Beds

2 Baths

2,286 Sq.Ft.

$949,000

MLS#: A4651805

PRICE REDUCTION! Waterfront 3BR Coastal Condo with Panoramic Bay Views!
Experience the pinnacle of island living in this recently refreshed 3-bedroom, 2-bath condo in the highly desirable Pelican Harbour & Beach Club on Longboat Key. Located on the second floor, this light-filled end unit offers sweeping Sarasota Bay views from the living room, primary suite, and your private screened-in balcony—ideal for morning coffee or sunset cocktails.

With over 1,600 sq ft of coastal-inspired living space, this residence features a spacious living room, tranquil dining area, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent updates include new carpet, furniture, recessed lighting, professionally painted interiors, mounted TVs, and a new AC and water heater (2024). Additional conveniences include in-unit laundry and covered parking.

Pelican Harbour offers resort-style amenities: 200 feet of private deeded beach with new lounge chairs, Heated pool & clubhouse, Marina with boat slips (up to 28 ft) & kayak launch, Tennis & pickleball courts, Pet-friendly.

Professionally managed, the community features new roofs, hurricane-rated carports. Ideally located mid-key, you're just minutes from St. Armands Circle, Bayfront Park, and the new St. Regis Resort.

Whether you're seeking a full-time residence, seasonal escape, or investment opportunity, this bayside retreat offers the perfect blend of luxury, comfort, and convenience.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE G2

3 Beds

2 Baths

1,794 Sq.Ft.

$949,000

MLS#: A4653045

Enjoy comfortable, coastal living in this well-appointed 2BR/2BA residence on the sought-after south end of Longboat Key. With over 1,500 sq. ft., this home features a neutral color palette and thoughtful design that enhances the natural beauty just outside. The kitchen offers classic white cabinetry with glass accents, granite countertops, stainless-steel appliances, and recessed lighting. A breakfast bar opens to the dining area, which flows into the spacious living room. Large sliding glass doors lead to the terrace, offering views of Sarasota Bay, the peaceful community lake and fountain, and the Gulf of Mexico - perfect for watching sunsets. The primary suite is light and airy, with terrace access and a full wall of glass. The en suite bath includes dual vanities, a walk-in shower, and a separate water closet. The guest suite also features generous space, plenty of storage, and its own full bath. Beachplace is a 31-acre gated community known for its mid-century modern design by Tim Seibert and its outstanding amenities: private beach access, a Jr. Olympic-sized pool, spa, kiddie pool, clubhouse with social activities, two fitness centers, sauna, tennis and pickleball courts, EV charging, and grilling stations. Rentals are allowed 12 times per year with a 30-day minimum. Residents also enjoy proximity to the prestigious Longboat Key Club, offering an exceptional lifestyle with 45 holes of championship golf, a world-class tennis center, a full-service marina, spa and wellness center, fine dining, and a private beach club - making it easy to enjoy the best of resort-style living just moments from home.

LONGBOAT KEY

1095 GULF OF MEXICO DRIVE 503

2 Beds

2 Baths

1,603 Sq.Ft.

$939,000

MLS#: A4648009

Experience the charm of historic Longboat Key living in this delightful 3-bedroom, 3-bathroom single-family home – Coastal Haven Cottage! Nestled in the heart of the village, you're just a short stroll away from pristine Gulf beaches and the area's renowned waterfront restaurants. Enjoy the convenience of golf cart access throughout the village and a quick ride over the bridge to explore the vibrant shops and beaches of Anna Maria Island. Back at home, unwind in the cozy outdoor area, complete with comfortable seating, a dining table for al fresco meals, and ample storage for all your beach and fishing gear. ROOM FOR A POOL - SEE PHOTO OF POOL! Offering a blend of classic charm and modern updates, including a 2020 roof, 2022 AC, new stainless-steel appliances, impact doors and windows, this home invites you to embrace the island life in this charming Longboat Key retreat. Additional offerings include covered carport and ample parking, fenced in yard, designer furnishings and finishes, and future rentals in place. Sold turnkey furnished, it's the perfect opportunity to immediately enjoy the coveted Longboat Key lifestyle!

LONGBOAT KEY

600 FOX STREET

3 Beds

3 Baths

1,427 Sq.Ft.

$899,999

MLS#: A4636248

MOTIVATED SELLER! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club.

A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining.

The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included.

Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle.

LONGBOAT KEY

2181 HARBOURSIDE DRIVE 1403

3 Beds

2 Baths

2,889 Sq.Ft.

$899,000

MLS#: A4656539

An exceptional INVESTMENT and lifestyle opportunity awaits in this completely TURNKEY FURNISHED, 2 bedroom/2 bath coastal retreat in the GULF FRONT property of Sand Cay on the world famous barrier island of Longboat Key. Located in a prime Gulf front complex with resort style amenities and its own private beach, this condo offers the perfect blend of relaxation, recreation, and return on investment. Sand Cay’s attractive 3-night minimum rental policy and its efficient, friendly on-site rental office make it easy to maximize your income earning potential while enjoying a private island getaway. The JANUARY-APRIL 2026 HIGH SEASON IS FULLY BOOKED WITH RENTALS, so your 2026 rental income is off to a great start. This inviting residence features gleaming, easy care ceramic tile floors, a full, granite clad kitchen with recessed & track lighting, and an exceptionally open living space illuminated by a wonderful large picture window bathing the space in natural light. A set of sturdy hurricane impact sliders opens into a generous private balcony that offers stunning views of lush tropical landscaping, the sparkling aquamarine pool, and a peekaboo glimpse of the Gulf. Both bathrooms have been tastefully updated with granite countertops, and ceiling fans in both bedrooms ensure year-round comfort. You’ll find plenty of closet storage for your towels and beach essentials. NEW HVAC system. Sand Cay is 60-unit boutique beachfront resort offering 100’ of private quartz sand beach, sparkling pool, tennis & pickleball court, beachside BBQ grills, newly resurfaced shuffleboard court, and convenient complimentary onsite laundry service. Known for its pristine beaches, upscale amenities, and peaceful atmosphere, Longboat Key provides the perfect backdrop for relaxation and recreation – just minutes from the boutiques and fine restaurants of St. Armands Circle and the cultural treasures of Sarasota – making this the perfect coastal sanctuary.

LONGBOAT KEY

4725 GULF OF MEXICO DRIVE 212

2 Beds

2 Baths

1,071 Sq.Ft.

$899,000

MLS#: A4657948

Exceptional opportunity to own this beautiful first-floor condominium at The Promenade, offering the perfect balance of comfort, and coastal charm with nearly 400 feet of private beach frontage and partial views of the Gulf of Mexico from almost every room.
This spacious two-bedroom, two-bathroom split floor plan features a bright, open layout ideal for entertaining or relaxed living. The kitchen flows seamlessly into the expansive living and dining areas, creating a connected and inviting space. Enjoy stunning northwest sunset views from the comfort of the great room or step outside to the private balcony for a peaceful retreat overlooking the Gulf.
The elegant primary suite offers balcony access, a large walk-in closet, and a spa-like en-suite bath with a soaking tub and walk-in shower. The generously sized guest bedroom is perfect for visitors or can be easily adapted as a home office or hobby room.
The Promenade offers a true resort-style experience with a 24-hour staffed gatehouse, full concierge services, and secure under-building assigned parking. Residents enjoy a heated Gulf-front pool and spa, a spacious sundeck with shaded gazebo and grilling area, four Har-Tru tennis courts, a well-equipped fitness center, a craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes the picture of effortless coastal living.
Don’t miss this rare opportunity to embrace the ultimate Longboat Key lifestyle, where every day feels like a vacation

LONGBOAT KEY

1211 GULF OF MEXICO DRIVE 105

2 Beds

2 Baths

1,788 Sq.Ft.

$899,000

MLS#: A4658394

Build Your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and approved. Architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with the beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or stepping out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.

LONGBOAT KEY

720 TARAWITT DRIVE

None Beds

None Baths

0.25 acres

$899,000

MLS#: A4633465

A rare offering of a penthouse end unit in this Gulf-front complex on southern Longboat Key. As you enter, you will notice an abundance of light, updated windows, floor-to-ceiling sliders, and a newer high-impact front door. The visual experience will take your breath away as your eyes scan an array of Gulf, golf course, intercoastal and city views. The penthouse offers the largest wrap-around balcony for this floor plan, to enhance your evenings with family and friends, capturing the gentle gulf breezes. Being an end unit, it offers two windows in this updated kitchen, complete with stainless steel appliances and a laundry closet. Pride of ownership is evident throughout this updated condominium, including but not limited to an updated HVAC, water heater, blinds throughout, with electric roller shades in the living room and primary bedroom. The primary bath is elevated with double vanities, updated light fixtures, a quartz countertop, and a walk-in shower. The updated guest bath features a quartz counter with a shower and bathtub, also supplying access to the guest bedroom. If an in-unit extra storage room is what you're looking for, it has that too. It also includes your own private parking space under the building. Building 6 is conveniently close to the Gulf, and clubhouse, which offers a Junior Olympic-sized pool, spa, kiddie pool, two fitness areas, saunas, grilling area, with plenty of shade and social activities. The community also offers private beach access with beach chairs and umbrellas, pickleball and tennis courts, EV charging stations and bike storage. Close to St. Armands Circle, shopping, restaurants and Sarasota, and all it offers.

LONGBOAT KEY

1065 GULF OF MEXICO DRIVE 601

2 Beds

2 Baths

1,412 Sq.Ft.

$895,000

MLS#: A4662468

One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!! WATERFRONT GEM ON LONGBOAT KEY – Priced UNDER $1M & Renovation Loan Eligible! This is your chance to own a waterfront home on Longboat Key for under $1 million! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Looking for even more space? The vacant lot next door is also for sale, making this a rare chance to tear down and build a custom waterfront compound. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today!

LONGBOAT KEY

636 TARAWITT DRIVE

2 Beds

2 Baths

2,294 Sq.Ft.

$895,000

MLS#: TB8368182

This beautifully remodeled Junior Suite offers peaceful lagoon views and a robust income stream. Sold fully furnished and part of the hotel program, it's a turnkey investment with resort-style perks. Unlike other buildings, this one features Junior Suites with soaring 10-foot ceilings, adding a sense of space and luxury. From your private terrace, watch manatees, dolphins, and a vibrant array of tropical birds glide by. As an owner in the hotel program, you will enjoy access to the exclusive 410-acre Longboat Key Club. Indulge in five upscale restaurants, 45 holes of championship golf, award-winning Tennis Gardens, spa and fitness center, a private white sand beach with umbrellas and waitstaff, and a full-service marina. Recent renovations to the rooms, pool, dining areas, and guest services elevate this already award-winning property, which proudly holds the AAA Four-Diamond Award. Whether for investment or leisure, this is your chance to live the Longboat Life.

LONGBOAT KEY

225 SANDS POINT ROAD 6201

1 Beds

1 Baths

642 Sq.Ft.

$890,000

MLS#: A4657026

Experience contemporary coastal living in this fully renovated, turnkey-furnished unit ideally located in the heart of Longboat Key! Nestled between 1,200 feet of private, powder-soft beach on the Gulf and a serene fishing pier on Sarasota Bay, this residence offers the perfect blend of island tranquility and luxury!Step inside to discover a meticulously cared for interior space updated with elegant flooring, a sleek kitchen, spa-inspired bathrooms, high-end appliances, tankless water heater, designer lighting, and custom furnishings throughout featuing a neutral yet distinctive décor, creating a relaxed coastal ambiance. Added conveniences include a full-size stacked washer and dryer in a discreet laundry closet, and a private under-building carport with a secure storage closet.Located within the architecturally significant Bayport Beach & Tennis Club, the community spans across 27 lush Gulf-to-Bay acres. Residents enjoy a wealth of resort-style amenities including: A private Gulf-front beach with chaise lounges and umbrellas, on site nature trails, lakes with fountains, a bayside fishing pier with kayak launch, heated Junior Olympic-sized pool, Har-Tru tennis courts, bocce ball, and a fitness center!

LONGBOAT KEY

750 BAYPORT WAY 750

2 Beds

2 Baths

1,570 Sq.Ft.

$869,000

MLS#: A4651083

COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY:
Welcome to a rare opportunity to embrace the BEST of coastal living on Longboat Key. Perched along the pristine shoreline, this meticulously maintained condo offers uninterrupted Gulf of Mexico views—where you can wake up to the gentle sound of waves and witness sunsets that transform the sky into a vibrant masterpiece. UPDATES GALORE: New AC, New Hot Water Heater, New Roof, New Luxury Flooring, New Hurricane Impact Resistant Sliding Doors, New Modern Bathroom. BEING SOLD TURN-KEY. EVERYTHING STAYS!
BRIGHT & INVITING INTERIORS: Step inside to discover an open, light-filled layout designed to maximize space and natural beauty. Large glass sliders seamlessly connect the interior to the outdoors, bathing the open kitchen and living area in natural light while blending modern functionality with coastal charm. The thoughtfully designed bedroom and bathroom serve as serene retreats, balancing comfort and style perfectly. YOUR PRIVATE OUTDOOR OASIS: Enjoy a standout private balcony that offers a front-row seat to the endless blue water and sandy beach. Whether savoring a quiet morning coffee or an evening cocktail, the gentle sea breeze creates an ideal setting for relaxation.
RESORT-STYLE COMMUNITY AMENITIES: Enhancing your lifestyle, the community boasts a range of well-maintained amenities including:
A sparkling pool, Tennis courts, shuffleboard, beach chairs, leasable boat slips, and a tranquil pavilion by the bayou for water enthusiasts.
UNMATCHED LOCATION & LIFESTYLE: This condo combines a highly desirable location with the privacy and comfort of a true coastal home—perfect for year-round living, a seasonal retreat, or a savvy investment. Adding to its appeal, the community features exclusively two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a streamlined, worry-free living
experience. Discover Longboat Key at its finest—where luxury meets laid-back coastal charm. Schedule your private tour today!

LONGBOAT KEY

6701 GULF OF MEXICO DRIVE 311

1 Beds

1 Baths

1,008 Sq.Ft.

$849,900

MLS#: A4640305

#A4660639

LONGBOAT KEY

2075 GULF OF MEXICO DRIVE T1-108

3 Beds

2 Baths

2,305 Sq.Ft.

$849,000

MLS#: A4660639

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