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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

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 18 of 34.

This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a small, waterfront, boutique midrise building containing only 9 residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

LONGBOAT KEY

490 N SHORE ROAD 6

2 Beds

2 Baths

2,367 Sq.Ft.

$750,000

MLS#: A4657668

Price reduced

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 7205

1 Beds

1 Baths

642 Sq.Ft.

$750,000

MLS#: A4657019

Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace. This particular condo has been tastefully updated with new HVAC with Wi-Fi thermostat in 2024; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.

LONGBOAT KEY

3070 GRAND BAY BOULEVARD 632

2 Beds

2 Baths

1,655 Sq.Ft.

$749,000

MLS#: A4627468

New on site 2 days ago

NEWLY REMODELED • COASTAL LUXURY RESIDENCE
Longboat Harbour • Unit 208 | Corner End Unit • Bay & Harbour Views.
Welcome to an exquisite, newly remodeled second-floor corner residence in the highly sought-after Longboat Harbour community. Reimagined with sophisticated coastal design, this light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour—creating a serene backdrop from morning to sunset.
This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available—especially those curated with such care and craftsmanship.
Step onto the private lanai and enjoy daily encounters with dolphins and manatees as they drift through the sparkling waterways.
________________________________________
A SHOWCASE KITCHEN WITH WATERVIEWS
Elegant, functional, and beautifully appointed:
• Frigidaire Professional stainless steel appliances
• Gleaming quartz countertops
• 9-inch deep sink
• Pull-out cabinet shelving
• Pantry closet
• Designer tile backsplash
• Two sunlit kitchen windows
• Large Eat-In Kitchen with water views & sunsets
• Instant hot-water feature
• Secondary kitchen door for enhanced flow
A perfect place for morning coffee or a relaxing meal surrounded by natural light.
________________________________________
LUXURIOUS PRIMARY SUITE
An elevated retreat designed for comfort and serenity:
• Private ensuite bath
• Custom California Closet walk-in wardrobe
• Built-in desk feature
• Remote-controlled luxury solar shades
A peaceful haven designed for rest and rejuvenation.
________________________________________
RESORT-INSPIRED AMENITIES
Longboat Harbour offers a lifestyle unmatched on the Gulf Coast:
• Designated covered parking spot conveniently located
• Personal storage space on the third floor
• Private deeded Gulf beach access with pavilion, restrooms & shower
• Four sparkling pools
• Fitness center & sauna
• Tennis & pickleball courts
• Billiards room, library & meeting rooms
• Picnic areas with grills
• Putting green
• Fishing pier
• Affordable resident-only boat dockage
• Kayak launch — and the seller is gifting a kayak to the new owner
Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key.
________________________________________
PROPERTY ENHANCEMENTS & UPDATES
Thoughtfully improved for comfort, reliability, and peace of mind:
• No hurricane damage or flooding
• Bosch Washer & Dryer
• Newer AC: 12/5/22
• Newer Hot Water Heater: 3/3/17
• New roofs throughout the community
• Electrical and plumbing systems updated
A beautifully renovated interior paired with essential system upgrades creates the perfect move-in-ready coastal residence.
________________________________________
THE ULTIMATE LONGBOAT LIFESTYLE
From sunrises over the Bay to evenings on the Gulf, this residence offers a lifestyle defined by beauty, serenity, and refined coastal living.
More than a home—this is luxury coastal living at its finest

LONGBOAT KEY

4350 CHATHAM DRIVE 208

2 Beds

2 Baths

1,316 Sq.Ft.

$749,000

MLS#: A4672221

Price reduced

REDUCED PRICE! Are you looking for a RESORT home with spacious rooms, fine finishes, vaulted ceilings and the convenience of a condo community with bay and beach access? Look no further. Luxury and style await in this beautifully updated townhouse, located behind the gates of the exclusive Bay Isles resort. With 1,590 sq. ft. of meticulously designed and finished indoor living space plus another 1,100 sq. ft. of screened lanai, storage and garage space, this resort home provides the ultimate in luxe living, comfort and convenience. Upon entering this home, you're greeted by an open concept great room and designer kitchen, vaulted ceilings, a conveniently placed guest bathroom, and views over the very private community pool. You'll never want to leave! The gourmet kitchen is a chef’s dream, featuring gleaming granite countertops including a striking azure blue granite breakfast bar, custom mosaic glass tile backsplash, solid wood cabinetry, and stainless JennAir appliances. Easy to maintain luxury vinyl plank floors flow throughout, adding sophistication and durability. Soaring cathedral ceilings and abundant natural light enhance the light, bright, spacious feel of this home and the private screened lanai offers a serene retreat with access to lushly landscaped grounds and the resort style pool. The oversized primary suite boasts vaulted ceilings, a walk-in closet, and an elegant ensuite bath with natural stone and custom tile shower. The second bedroom also has a vaulted ceiling plus walk-in closet and beautifully finished adjacent bathroom. The ground-level garage has extra depth enabling covered parking for two cars plus there's a separate room that can be flexibly used for storage, a home gym, or a wine cellar. As a Bay Isles resident, you'll enjoy exclusive access to resident-only amenities including a private clubhouse, fitness center, heated pool and spa, tennis courts, and the private Bay Isles Beach Club. This resort home is just minutes from the vibrant dining, shopping, and cultural scene of St. Armands Circle and downtown Sarasota. See this home today and enjoy the best of Longboat Key living.

LONGBOAT KEY

1928 HARBOURSIDE DRIVE 1403

2 Beds

2 Baths

2,606 Sq.Ft.

$745,000

MLS#: A4645559

Coastal Elegance on Longboat Key – Assessments Paid in Full!
Beachfront Living Redefined
Welcome to an extraordinary beachfront retreat where the serene rhythm of the Gulf meets
refined island living. This beautifully appointed two-bedroom, two-bath residence offers
beautiful views of the common grounds, entrance and tennis courts.
A rare gem among beachfront properties, this home boasts an expansive private terrace
that wraps around the unit, creating over 60 feet of seamless outdoor living space. Whether
you're entertaining under the stars or savoring a quiet morning coffee with the sound of
waves as your backdrop, this exceptional setting elevates every moment.
Inside, the open-concept living and dining areas are bathed in natural light, framing
sweeping views through floor-to-ceiling glass sliding doors. The well-appointed kitchen
features Kitchen-Aid appliances and ample cabinetry, perfectly suited for both casual
meals and elegant entertaining. For the discerned buyer, there is comfort in knowing that
the End-Windows are ordered to be replaced, New Elevators, New Roof, New Porte
Cochere, New Gym, New Rec room, New Landscaping, New Saunas located in the
remolded locker rooms, 2020 Water Heater, 2016 Bosch HVAC, Humidistat in unit,
Hurricane Windows and Doors, Assigned Parking Space, 24/7 maintenance member of
staff lives on site, condo management company is located on site to assist with all
requests.
The spacious primary suite is a true sanctuary, where gentle sea breezes and panoramic
views invite total relaxation. The en-suite bath adds a touch of luxury, while the second
bedroom offers flexibility as a welcoming guest suite or a tranquil home office.
Located in the beautiful Islander Club, residents enjoy 400 feet of private beach frontage
and a host of resort-style amenities, including a heated beachfront pool, fitness center,
renovated clubhouse, saunas, billiards and table tennis room, and one Har-Tru tennis
court and two new Pickle ball courts. The residence also has Two Fishing piers for the avid angler or photographer that would like to immerse themselves into the abundant sea life that awaits them. On-site management ensures peace of mind, while the world-class shopping,
dining, and cultural experiences of St. Armands Circle and downtown Sarasota are just
moments away.
This is more than a home—it's a rare opportunity to live the coveted Longboat Key
beachfront lifestyle, where elegance meets the sea and every day feels like a vacation.

LONGBOAT KEY

2301 GULF OF MEXICO DRIVE 45N

2 Beds

2 Baths

1,485 Sq.Ft.

$729,000

MLS#: A4668142

Nestled in the sought-after Fairway Bay community on Longboat Key, this 2BR, 2BA residence offers the perfect blend of serene bayfront living and luxurious amenities, all behind the exclusive gates of Bay Isles. As an end unit, first floor walk-down, the layout maximizes natural light, with expansive windows framing stunning southeast-facing views of Sarasota Bay, a deep-water canal and lush tropical greenery. The oversized, open patio feels like a private extension of your living space and an ideal spot for relaxing or entertaining while enjoying bay breezes. The updated kitchen features rich wood cabinetry, stone countertops, stainless steel appliances and a convenient breakfast bar that connects seamlessly to the dining area. A second terrace off the breakfast room/office offers additional outdoor space for more serene moments. The spacious primary suite, bathed in natural light, includes access to the terrace and a large en-suite bath with dual vanities and a separate water closet. The updated bathrooms continue the residence's refined aesthetic. With furnishings negotiable and abundant storage throughout, you will feel a sense of spaciousness like being in a single-family home, all within this sought-after community. Fairway Bay is a pet-friendly community where residents enjoy a wealth of amenities, including under-building parking, extra storage, beautifully landscaped grounds, tennis courts, a community pool and a fitness center. The private Bay Isles Beach Club membership offers deeded beach access, and with 24-hour gated security, peace of mind is guaranteed. CVS and Publix are nearby and St. Armands Circle and Sarasota’s vibrant cultural scene are just a short drive away.

LONGBOAT KEY

1932 HARBOURSIDE DRIVE 217

2 Beds

2 Baths

1,752 Sq.Ft.

$729,000

MLS#: A4671330

Price reduced

This spacious waterfront villa lives like a single-family home yet offers the ease
of maintenance-free living! Enjoy breathtaking Sarasota Bay and canal views from this 1,900
sq. ft. residence—the largest in the community. Thoughtfully designed, it features a waterfront
great room, two generously sized bedrooms, two beautifully updated bathrooms, and a versatile
bonus room that can serve as a third bedroom, home office, or private in-law/nanny suite with its
own exterior entrance. The open-concept kitchen overlooks the great room and boasts quartz
counters, abundant cabinetry, new stainless-steel appliances, and ample workspace. A separate,
oversized laundry room with newer full-sized machines even offers the potential to add a third
bathroom. The waterfront Florida room and private patio are perfect for grilling the catch of the
day, dining under the stars, or watching manatees and dolphins swim by. Inside, an attractive
neutral palette, easy-care luxury vinyl plank flooring (no carpet), and hurricane-impact windows
provide both comfort and peace of mind. The attached covered carport allows easy access for
groceries and luggage. Windward Bay offers exceptional resort-style amenities: two heated pools
with complimentary chaises, saunas, tennis and pickleball courts, a fitness center, shuffleboard,
boat slips ($45/month or $50/month with an owner-supplied lift), kayaking and paddleboarding
(storage/launches $35/year), fishing, and three deeded beach accesses. Stroll or bike through 26
acres of professionally landscaped bayfront grounds, or head across the street to Zota Beach
Resort for fine dining and sunset cocktails. This proactive community has passed its structural
integrity inspection and is certified for another ten years. Owners may rent twice per year with a
one-month minimum and no ownership waiting period—ideal for generating income while
enjoying a peaceful coastal lifestyle. Exceptionally pet-friendly, Windward Bay welcomes two
large pets up to 75 lbs each, with pet comfort stations throughout the property. Even Renters can
have pets…a uniquely appealing feature for those seeking rental income. Seize this rare
opportunity to own a tranquil island haven that combines space, style, and simplicity in a
paradise-like setting. What could be better? It could be yours!

LONGBOAT KEY

4976 GULF OF MEXICO DRIVE Villa 18

3 Beds

2 Baths

2,283 Sq.Ft.

$725,000

MLS#: A4665034

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.

$720,000

MLS#: A4632978

#A4669086

LONGBOAT KEY

1065 GULF OF MEXICO DRIVE 201

2 Beds

2 Baths

1,312 Sq.Ft.

$719,000

MLS#: A4669086

New on site 2 days ago

Set in the sought-after Longboat Harbour community on Longboat Key, this beautifully updated 2BR/2BA walkout residence offers 1,152+/- sq. ft. of inviting waterfront living. Your breath will be taken away by the peaceful mangrove-lined views that shape a relaxed, effortless way of life. The moment you step inside, the level of care and style is unmistakable, as crown molding, maintenance free tile and laminate floors create a warm, welcoming ambiance that draws you toward the picturesque backdrop beyond the living space. The kitchen has been thoughtfully updated with stone countertops, all-white cabinetry, stainless-steel appliances, a tile backsplash (with under cabinet lighting), recessed lighting and a tray ceiling with fan. A large breakfast bar connects the kitchen to the dining area and living room, giving the entire layout an open, seamless flow. The former terrace has been enclosed to create an extended Florida room wrapped in sliders with privacy shades, offering a stunning vantage point over the water and direct walkout access to the outdoors. It’s a rare feature that brings the waterfront right to your door and is only steps away from one of the bayside pools. The primary bedroom enjoys soothing water views along with a graciously redesigned bath featuring rich wood cabinetry and refined finishes. The guest bedroom is equally comfortable for family or visitors, and the updated guest bath continues the home’s cohesive style. Residents of Longboat Harbour enjoy an exceptional list of amenities across both bay and beach, including berths for more than 50 boats on the Sarasota Bay side and exclusive Gulf access through a private beach house with restrooms, showers and dedicated parking. Additional amenities include 4 swimming pools, a tennis court, fitness center, wood shop, art studio, banquet hall and an active schedule of social events.

LONGBOAT KEY

4430 EXETER DRIVE 106

2 Beds

2 Baths

1,152 Sq.Ft.

$710,000

MLS#: A4671849

Don't miss the opportunity to build your dream home in one of Longboat Key’s most sought-after, established neighborhoods. Nestled right next to Joan M. Durante Bayfront Park and with beach access across the street you'll have quick access to the pristine, world-renowned Gulf of Mexico beaches. The newly restored seawall (2021) with wide concrete cap and raised dock with nautical dock lights at each pier also features a 10,000 lb lift (elevator type) and is the perfect place to house your boat with quick access to Sarasota Bay and waterways beyond! The lot offers lovely mature trees and plenty of room for a pool. No HOA or CDD. Seller will provide existing house plans from Topsider Homes (any changes to plans would come at the expense of the buyer). Topsider Homes is a luxury builder that offers a design center for picking finishes and is experienced in building in hurricane prone areas. Prefer a renovation project? The existing Old Florida-style 2-bedroom, 1.5-bath ranch home with classic terrazzo floors offers tons of charm and potential. With a bit of vision, it could become a cozy primary residence or an income-producing rental.

LONGBOAT KEY

755 SAINT JUDES DRIVE N

2 Beds

1 Baths

1,582 Sq.Ft.

$700,000

MLS#: A4661485

Don't miss the opportunity to build your dream home in one of Longboat Key’s most sought-after, established neighborhoods. Nestled right next to Joan M. Durante Bayfront Park and with beach access across the street you'll have quick access to the pristine, world-renowned Gulf of Mexico beaches. The newly restored seawall (2021) with wide concrete cap and raised dock with nautical dock lights at each pier also features a 10,000 lb lift (elevator type) and is the perfect place to house your boat with quick access to Sarasota Bay and waterways beyond! The lot offers lovely mature trees and plenty of room for a pool. No HOA or CDD. Seller will provide existing house plans from Topsider Homes (any changes to plans would come at the expense of the buyer). Topsider Homes is a luxury builder that offers a design center for picking finishes and is experienced in building in hurricane prone areas. Prefer a renovation project? The existing Old Florida-style 2-bedroom, 1.5-bath ranch home with classic terrazzo floors offers tons of charm and potential. With a bit of vision, it could become a cozy primary residence or an income-producing rental.

LONGBOAT KEY

755 SAINT JUDES DRIVE N

None Beds

None Baths

0.25 acres

$700,000

MLS#: A4661483

Turnkey-Furnished Longboat Key Condo with Dock Access & Short-Term Rental Potential
Experience the best of coastal living in this beautifully furnished turnkey condo on highly sought-after Longboat Key. Perfect as a personal getaway or an income-producing investment, this residence is one of the rare properties that allows short-term rentals, giving you exceptional flexibility and earning potential.
Step inside to a bright, inviting interior that blends comfort and style, fully outfitted so you can move right in or start renting immediately. Just outside your door, enjoy a beautiful waterfront dock, ideal for watching sunsets, launching a kayak, or simply relaxing after a day at the beach.
Nestled in a prime location close to pristine Gulf beaches, dining, shopping, and the best of island living, this condo offers the perfect combination of convenience and charm.
Whether you're seeking an island retreat, a rental-ready investment, or both, this Longboat Key gem delivers.

LONGBOAT KEY

5310 GULF OF MEXICO DRIVE 16

2 Beds

2 Baths

1,118 Sq.Ft.

$699,000

MLS#: A4673264

#A4671087

LONGBOAT KEY

4900 GULF OF MEXICO DRIVE 205

2 Beds

2 Baths

1,312 Sq.Ft.

$698,000

MLS#: A4671087

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