Longboat Key Homes with Sidewalks Community Features

Welcome to Longboat Key, Florida—a picturesque barrier island that embodies the perfect blend of tranquility and coastal charm. Nestled between the Gulf of Mexico and Sarasota Bay, Longboat Key is renowned for its stunning white-sand beaches, crystal-clear waters, and vibrant sunsets that paint the sky in hues of orange and pink. This idyllic locale is not just a paradise for sun-seekers; it also boasts a rich tapestry of cultural experiences, from art galleries and fine dining to boutique shopping and world-class golf courses.

One of the standout features of Longboat Key is its commitment to community living, particularly in neighborhoods designed with sidewalks that encourage a sense of connection and outdoor enjoyment. These homes with sidewalks create a welcoming atmosphere, perfect for evening strolls, morning jogs, or simply enjoying a leisurely bike ride. Families can be seen enjoying the outdoors, fostering a sense of community and safety that is hard to find elsewhere.

In addition to the beautiful homes, residents of Longboat Key benefit from a variety of amenities, including lush parks, tennis courts, and access to private beach clubs. Whether you're looking for a vacation retreat or a permanent residence, the homes here are designed to provide comfort and luxury, all while being just a stone's throw away from the stunning natural beauty that surrounds them.

With its charming neighborhoods and vibrant community spirit, Longboat Key is not just a place to live—it's a lifestyle waiting to be embraced. Come discover the magic of this coastal gem and find your dream home today!

Newest Longboat Key Homes with Sidewalks Community Features

760 Longboat Court, Longboat Key $840,000

Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, ...

3 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

1591 Gulf Of Mexico Drive Unit 312, Longboat Key image

1591 Gulf Of Mexico Drive Unit 312, Longboat Key — Champagne $4,290,000

Tucked into the Champagne Building at The Residences at The St. Regis Longboat Key, unit 312 is a fully furnished coastal residence done right. Ceilings soar, glass walls...

2 Beds
3 Baths
St Regis SubDv.
34228 Zip Code

2800 Harbourside Drive Unit E-21, Longboat Key image

2800 Harbourside Drive Unit E-21, Longboat Key $385,000

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion...

Longboat Key Moorings SubDv.
34228 Zip Code

4600 Gulf Of Mexico Drive Unit 301, Longboat Key image

4600 Gulf Of Mexico Drive Unit 301, Longboat Key — E Building $670,000

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nea...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

843 Bayport Way Unit 843, Longboat Key image

843 Bayport Way Unit 843, Longboat Key — F $645,000

LONGBOAT KEY LIVING—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, where island living means having the beach, bay, tennis, kayaking, and resort-style ...

2 Beds
2 Baths
Bayport Bch & Ten SubDv.
34228 Zip Code

521 Forest Way, Longboat Key — N/A $599,900

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars T...

2 Beds
3 Baths
Cedars East SubDv.
34228 Zip Code

732 Bayport Way, Longboat Key — 732 $1,050,000

Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat...

2 Beds
2 Baths
Bayport Bch & Ten SubDv.
34228 Zip Code

2020 Harbourside Drive Unit 442, Longboat Key image

2020 Harbourside Drive Unit 442, Longboat Key — M-4 $699,000

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within t...

2 Beds
2 Baths
Fairway Bay SubDv.
34228 Zip Code

1561 Gulf Of Mexico Drive Unit 404, Longboat Key image

1561 Gulf Of Mexico Drive Unit 404, Longboat Key — Armand $12,750,000

Presented in the most coveted beachfront enclave at The St. Regis Longboat Key Resort, this is a rare opportunity to own a spectacular residence in the prestigious Armand...

3 Beds
4 Baths
St Regis SubDv.
34228 Zip Code

5055 Gulf Of Mexico Drive Unit 115, Longboat Key image

5055 Gulf Of Mexico Drive Unit 115, Longboat Key — 1 $750,000 ▼

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s sought-after beachfront communities. This beautifully updated three-...

3 Beds
2 Baths
Club Longboat Beach & Tennis SubDv.
34228 Zip Code

765 Saint Judes Drive N, Longboat Key image

765 Saint Judes Drive N, Longboat Key $1,350,000

Virtually Staged. VIRTUALLY EVERYTHING NEW — BOAT IN YOUR BACKYARD, PRIVATE BEACH DOWN THE STREET. This is the Longboat Key lifestyle buyers dream about: boating from you...

4 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

2800 Harbourside Drive Drive Unit M-10, Longboat Key image

2800 Harbourside Drive Drive Unit M-10, Longboat Key $289,000 ▲

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enj...

Bay Isles SubDv.
34228 Zip Code