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

Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

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

One of the most popular communities provided by Michael Graf

417

# of Listings

2

Avg # of Bedrooms

$1,122

Avg. $ / Sq.Ft.

$2,032,790

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

417 Properties Found. Page 20 of 28.

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

1,590 Sq.Ft.

$745,000

MLS#: A4645559

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.

$729,900

MLS#: TB8462750

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

1,442 Sq.Ft.

$729,000

MLS#: A4671330

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

1,900 Sq.Ft.

$725,000

MLS#: A4665034

Price reduced

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 offering sunrise and sunset views. 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

1,276 Sq.Ft.

$724,900

MLS#: A4627468

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

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

1,014 Sq.Ft.

$699,000

MLS#: A4673264

#A4669086

LONGBOAT KEY

1065 GULF OF MEXICO DRIVE 201

2 Beds

2 Baths

1,172 Sq.Ft.

$699,000

MLS#: A4669086

New on site 2 days ago

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.

$699,000

MLS#: A4675727

#A4671087

LONGBOAT KEY

4900 GULF OF MEXICO DRIVE 205

2 Beds

2 Baths

1,312 Sq.Ft.

$698,000

MLS#: A4671087

Coastal Elegance on Longboat Key – 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

1,235 Sq.Ft.

$695,000

MLS#: A4668142

Price reduced

Price reduced to sell! Seller says all offers considered. Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key retreat on 26 bayfront acres, with half a mile of walking trails along the Bay. This 1,312 sq ft residence features an open coastal layout, a bright remodeled kitchen with quartz countertops, and an oversized living area designed to frame the waterfront views. Step into the lanai and look out over the marina, mangroves, and wildlife — a tranquil backdrop that changes with the tides. The building’s rare pet policy allowing two pets, combined with its waterfront lifestyle, makes this one of the most desirable opportunities on Longboat Key. Enjoy beach access, 2 heated pools, 6 pickleball courts and tennis courts, kayak storage, bike storage, walking trails, fitness amenities, firepits, barbecue grills, picnic tables, 2 marinas, fishing piers, shuffleboard, clubhouse with a kitchen, library, fitness room, meeting room, 2 saunas, and walkability to restaurants. Whether you’re seeking a seasonal escape or a full-time coastal home, #202 delivers a relaxed, elevated lifestyle with a view you’ll never forget.

LONGBOAT KEY

4500 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,312 Sq.Ft.

$695,000

MLS#: A4664363

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

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

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

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

LONGBOAT KEY

3070 GRAND BAY BOULEVARD 612

2 Beds

2 Baths

1,371 Sq.Ft.

$689,500

MLS#: A4671489

Introducing a remarkable opportunity to own a piece of paradise at 723 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. This property provides an exceptional opportunity to enjoy all that Longboat Key has to offer, with proximity to sandy shores and a serene environment.

As you enter the property, you are greeted by a spacious and functional floor plan that maximizes natural light. The kitchen features modern appliances and ample counter space, making it ideal for both cooking and entertaining. The sleek cabinetry provides a contemporary aesthetic, while the adjoining living and dining area ensures a seamless flow throughout the home, perfect for gatherings with family and friends.

The open layout allows for easy interaction between spaces, enhancing the overall living experience. Large windows in the living room capture stunning views and fill the space with sunshine, creating a warm and inviting atmosphere. The combination of warm toned laminate flooring and soft color palettes contributes to the property’s relaxed elegance.

Outdoor amenities include well-maintained landscaping that enhances the overall curb appeal of the property. The outdoor areas are perfect for enjoying Florida’s inviting climate. Whether you’re lounging in the garden or taking a short walk to the beach, this location offers a unique coastal lifestyle.

This residence is not just a home—it’s a beachside retreat that promises tranquility and leisure. With its close proximity to the water and the conveniences of Longboat Key, this property presents a rare opportunity for those looking to embrace the Florida lifestyle. Schedule a visit today to explore all the potential that 723 Bayport Way has to offer.

LONGBOAT KEY

723 BAYPORT WAY 723

2 Beds

2 Baths

1,486 Sq.Ft.

$685,000

MLS#: TB8463039

#A4643486

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE Q2

2 Beds

2 Baths

1,150 Sq.Ft.

$684,900

MLS#: A4643486

1 ... 18 19 20 21 22 ... 28

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

What is 3 + 4 ?

Reason for contacting?

Buying a home

Selling a home

Other

I agree to receive email communication and understand I can unsubscribe at any time.

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Accessibility Menu

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

I agree to receive communications and understand I can unsubscribe at any time.

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service