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

Long Boat Key

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker

455

# of Listings

2

Avg # of Bedrooms

$1,128

Avg. $ / Sq.Ft.

$2,046,259

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

455 Properties Found. Page 23 of 31.

#A4643486

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE Q2

2 Beds

2 Baths

1,150 Sq.Ft.

$684,900

MLS#: A4643486

Price reduced

Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout.
The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind.
Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space.
On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop.
Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities.
Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities.

LONGBOAT KEY

1920 HARBOURSIDE DRIVE 1003

2 Beds

2 Baths

1,590 Sq.Ft.

$684,500

MLS#: TB8462750

Price reduced

SELLER SAYS “SELL!” Unbeatable opportunity at $689,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit listing since December 30, 2021, in the highly desirable community of Windward Bay. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.

LONGBOAT KEY

4960 GULF OF MEXICO DRIVE 206

2 Beds

2 Baths

1,523 Sq.Ft.

$679,900

MLS#: A4679160

Whether you choose resort style living or just want to enjoy vacationing at the beach while earning income when you are not using your condo then this is the place for you! This unit is consistently booked and 2026 is already filling up fast! The entrance to this unit is via beautiful pergolas and lush landscaping, which immediately sets the vibe for a tropical getaway. The resort is right on the beach and amenities include a large heated pool, several grills, tennis, basketball and pickleball. Repeat guests have commented choosing this unit because of its location and that they love having a screened in patio to enjoy morning coffee or simply the warm gulf air. Casa Del Mar is one of the few resorts in Longboat permitted to offer short term rentals and also offers some of the lowest property management fees as well. Come check out this turnkey 2 bedroom 2 bath condo and make beach living your reality! (approximately 900 sqft with screened in lanai)

LONGBOAT KEY

4621 GULF OF MEXICO DRIVE 10D

2 Beds

2 Baths

756 Sq.Ft.

$675,000

MLS#: TB8453208

Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis Resort. This Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space and combines comfort, convenience. There are 2 balconies one off the living room and the second off the master bedroom. Watch a game of tennis and enjoy the salt air as you unwind with your favorite drink. This is a well maintained residence and some upgrades include: (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. 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. The resort has an expansive calendar full of activities outdoors and the clubhouse has gatherings and various events. 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 (one of which is private for adults only), 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

Lifestyle, location, and amenities are the reason you come to Buttonwood Cove. This intimate community of just 56 residences presents the ultimate in Gulf Coast living on Longboat Key. This rarely available 3-bedroom, 2.5-bath condominium offers a lifestyle defined by ease, beauty, and convenience. Owners can walk across the street to deeded beach access, complete with provided beach chairs, perfect for relaxing on the white-sand shores. This unit benefits from Gulf of Mexico views from the front and serene bay views from the rear—a truly special island setting from sunrise to sunset.

Inside, an airy open layout is filled with natural light. The spacious living and dining areas are bathed in sunshine and open to tranquil bay views, creating a peaceful backdrop of water, passing boats, and coastal skies. Glass sliders lead to a private Gulf-facing lanai, perfect for enjoying sea breezes and sunsets. Adding to the appeal are three generously sized bedrooms, two full bathrooms, and a half bath with laundry—everything you need under one roof.

Buttonwood Cove offers a quieter, more private island experience and has undergone numerous updates in recent years, providing peace of mind to owners. Improvements include a newer roof, elevators, driveways, exterior paint, and Trex docks. This well-managed, amenity-rich waterfront community features lush tropical landscaping, a heated community pool, tennis and pickleball courts, a fishing pier, kayak launch, under-building parking, and private storage for beach and island essentials. The community is pet-friendly for small dogs and cats and is up to date on all milestone and structural inspections, allowing the new owner to move in with confidence.

Golf enthusiasts will appreciate the close proximity to the Longboat Key Club, where residents are welcome to explore membership opportunities and enjoy two championship golf courses along with the club’s full suite of amenities.

Ideal as a full-time residence or seasonal retreat, this location provides outstanding convenience. Everyday essentials, including grocery stores and pharmacies, are just minutes away, while Sarasota-Bradenton International Airport is approximately 12 miles away, the renowned shops and restaurants of St. Armands Circle are about 6 miles away, and downtown Sarasota—home to world-class culture, dining, and shopping—is just 9 miles away.

Island living made easy—welcome home to Buttonwood Cove.

LONGBOAT KEY

3500 GULF OF MEXICO DRIVE 104

3 Beds

2 Baths

1,486 Sq.Ft.

$675,000

MLS#: A4675727

LOCATION, LOCATION, LOCATION!!! Discover a rare and recently cleared premium homesite located on one of Longboat Key’s most charming and historic streets. This exclusive New Pass Shores community features only 6 homes, providing an intimate neighborhood atmosphere. While this homesite is not directly on the waterfront, it includes a NEW composite wood boat dock shared with just 3 other homes, granting you fishing and boating access or a peaceful retreat to enjoy the beauty of Sarasota Bay's waters and wildlife.
This property represents the perfect blend of luxury, convenience, and serene coastal living, making it an ideal location to build your dream home or investment property. Nestled on the highly sought-after southernmost part of the key, it is within walking and biking distance to both Sarasota Bay and the beach.
Living on Longboat Key means more than a home — it’s a lifestyle. From the pristine beaches and world-class golf and tennis at the Resort at Longboat Key Club (membership required) to boutique shopping and fine dining on St. Armand's Circle, and cultural attractions just minutes away in Sarasota, you’ll enjoy the perfect balance of island tranquility and vibrant city life as well as quick access to SRQ airport!
All measurements are approximate; it is the buyer's responsibility to verify the boundaries and accuracy of all information provided

LONGBOAT KEY

525 CHANNEL LANE

None Beds

None Baths

0.14 acres

$675,000

MLS#: A4676908

Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.

LONGBOAT KEY

3080 GRAND BAY BOULEVARD 515

2 Beds

2 Baths

1,276 Sq.Ft.

$659,000

MLS#: A4674001

Experience coastal living in this impeccably renovated condominium in the beautiful gated community of Longboat Harbour on Longboat Key. This residence is on the top floor, in one of the sought-after buildings on the property, given the expansive views of Sarasota Bay. It's a striking view when you enter this home. Sarasota Bay is visible from nearly every room, including the living area, dining area, open kitchen, lanai and primary bedroom. Thoughtfully renovated, the condominium is in pristine, move-in-ready condition and is being sold turnkey furnished with high-end furniture and finishes throughout. The open-concept kitchen features premium cabinetry, Cambia quartz countertops, stainless steel appliances and a breakfast bar that flows seamlessly into the living space, all framed by stunning bay views. The primary bedroom suite includes two built-in wood units for efficient storage, as well as a custom closet. The views from the bedroom are simply serene with exceptional water vistas, creating a private retreat. The second bedroom is spacious and has been freshly painted. All closets have custom built-ins. Both baths feature spacious, walk-in showers. Plantation shutters in bedrooms. This is easy living with covered parking, an elevator and a private storage unit included. There are impact-rated windows and sliding doors in this home as well as a new HVAC system and new roof, providing exceptional value for the buyers. Longboat Harbour offers a yacht club atmosphere with resident boat dockage available at reasonable rates, multiple swimming pools, kayak storage, a putting green, tennis courts, a robust pickleball community, a fitness center and a clubhouse hosting a variety of social activities. Residents also enjoy deeded beach access just across the street with gated parking and facilities, completing the ideal island lifestyle. Enjoy spectacular sunsets every night. Whether as a full-time residence or a refined coastal getaway, this exceptional bayfront condominium delivers unmatched views, luxury finishes and best of Longboat Key living. It's more than a place to call home, it's where you'll make memories and friends to last a lifetime.

LONGBOAT KEY

4420 EXETER DRIVE 307

2 Beds

2 Baths

1,152 Sq.Ft.

$650,000

MLS#: A4678151

Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Inside, the kitchen showcases granite countertops and rich wood cabinetry, while both bedrooms are en-suite for privacy and convenience. Lovingly maintained as a part-time vacation retreat since 1989, the condo reflects light use and thoughtful care.Fairway Bay, within Bay Isles, offers a true resort lifestyle with swimming pools, spas, tennis courts, a fitness center, and a welcoming clubhouse for social gatherings. As a Bay Isles resident, you’ll also have access to the private Bay Isles Beach Club, where you can relax on pristine Gulf shores or reserve the clubhouse for special occasions.This coveted location places you within walking distance of a marina, Publix, CVS, and local shops, while just minutes away you’ll find St. Armands Circle (5 miles), downtown Sarasota (8 miles), and all the cultural, dining, and shopping options the Gulf Coast is known for. Bay Isles is also home to 27 holes of championship golf, the world-class Tennis Gardens, the Longboat Key Moorings Marina, and two of the five acclaimed restaurants of the Longboat Key Club—where memberships are available separately. Live every day like you’re on vacation in this exceptional Gulf Coast retreat.

LONGBOAT KEY

1932 HARBOURSIDE DRIVE 254

2 Beds

2 Baths

1,192 Sq.Ft.

$650,000

MLS#: A4666650

Is it possible to say that there is a “BEST’ location on Longboat Key? If sunrises over the Bay from your comfy chair captivate you….. if striking sunsets on the beach, over the Gulf waters leave you mesmerized…. If short strolls with your pooch to the local paw-park are a favorite part of your daily routine….. or if launching your kayak/ paddleboard or loading up the boat for a stressless day on the water are what you look most forward to…… then yes! There is a BEST place and it is called Pelican Harbour. Amenity rich and located mid-key, you can do all of this and so much more. Piece of mind is another attribute of this ground floor 2bed/2bath home on the quiet north side of the community because it remained completely dry and unharmed during the storms of 2024- not a drop of water intrusion here! Qualities of this home include impact windows and sliders, consistent tile floor throughout, full size in-unit washer/dryer, whole home water filtration system, plantation shutters and updated baths both with walk-in showers. Pelican Harbour is aesthetically pleasing with a leisurely vibe. Excellent thought and care were put into the recently updated clubhouse, pool furnishings, bayfront sitting dock and landscaping as well as new roofs, hurricane safe carports, tennis and pickleball courts and boat docks. We are pet-friendly and there are currently boat docks available for a very reasonable annual fee.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE U1

2 Beds

2 Baths

1,150 Sq.Ft.

$650,000

MLS#: A4677626

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

LONGBOAT KEY

5260 GULF OF MEXICO DRIVE 403

2 Beds

2 Baths

1,128 Sq.Ft.

$649,999

MLS#: A4677090

Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit!
Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms, while the pool lies just steps from your private patio.
Elegantly remodeled, the home showcases porcelain tile floors, solid doors, crown molding, granite windowsills, and solar film on rear windows and sliders for added privacy and comfort. The open, light-filled kitchen is a chef’s delight, featuring solid wood cabinetry, granite countertops, stainless steel appliances, and a double oven range. Both bathrooms are thoughtfully updated with cast-iron tubs, granite countertops, and dedicated heat and air vents.
Additional highlights include a full-size in-unit washer and dryer, a large water heater, and covered parking space #67 . The residence comes with a long-standing seasonal tenant and a transferable lease.
Located in the premier M Building at Longboat Harbour, residents enjoy resort-style amenities including a private gated beach club(4415 Gulf Of Mexico dr ), four heated pools, tennis and pickleball courts, fitness center, kayak storage, and boat docks on first come base- power and sail boats. A new roof is underway with assessment already paid, and no storm damage has occurred.
This is a rare opportunity to own a move-in-ready, elegantly upgraded waterfront retreat in one of Sarasota’s most sought-after communities.

LONGBOAT KEY

4430 EXETER DRIVE M108

2 Beds

2 Baths

1,376 Sq.Ft.

$649,900

MLS#: A4676513

Welcome to this beautifully updated first-floor waterfront condominium offering two bedrooms, two bathrooms, and a glass-enclosed lanai, all sold for effortless coastal living. Enjoy tranquil canal views with passing boats and frequent manatee sightings, delivering an authentic Florida waterfront experience right outside your door.

The open-concept kitchen has been fully remodeled and features granite countertops, new cabinetry, stainless steel appliances, ceramic tile flooring, and fresh interior paint. Tile floors extend throughout the main living areas, while new carpeting enhances the comfort of the second bedroom. Both bathrooms were tastefully renovated in 2022, and a new A/C system installed in 2021, Hurricane Windows and Doors , ensure year-round comfort and peace of mind.

Offered fully furnished, this inviting residence includes tasteful décor, artwork, and kitchenware, making it ideal for immediate occupancy, seasonal use, or investment.

Located within Longboat Harbour, a gated waterfront community, residents enjoy an impressive collection of resort-style amenities. Highlights include deeded private beach access with a beachfront pavilion featuring gated Gulf access, restrooms, hot showers, lockers, parking, and a convenient car wash area. Additional amenities include boat docks, four heated pools, a recently updated clubhouse with banquet hall, library, arts and crafts room, billiards and card rooms, a fully equipped fitness center, tennis and pickleball courts, barbecue grills, kayak storage, and additional storage rooms. When available, boat slips accommodating vessels up to 34 feet are offered for a nominal annual fee.

This is a rare opportunity to own a turnkey waterfront residence on the ground floor with exceptional amenities in one of Longboat Key’s most desirable communities. Call today to set up your private showing!

LONGBOAT KEY

4380 EXETER DRIVE H-103

2 Beds

2 Baths

1,152 Sq.Ft.

$649,900

MLS#: A4675171

Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar. You and your guests will relish the gulf-front pool, tennis courts with pickleball, grilling area and picnic tables, all while basking in the soothing embrace of the gulf waters as the simple, fulfilling life awaits. For those who wish to travel light, the unit is turnkey furnished, fully equipped, and ready to provide your ideal beach getaway. Upgrades include new kitchen and baths, quartz countertops and tile throughout, and stainless-steel appliances. The unit comes with a washer and dryer. just a short drive to local restaurants, Anna Maria Island, local parks, grocery shopping, CVS, places of worship, banks, world-renowned St, Armands Circle, top-rated Sarasota and all it offers.

LONGBOAT KEY

4621 GULF OF MEXICO DRIVE 16B

2 Beds

2 Baths

900 Sq.Ft.

$649,900

MLS#: A4632978

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