Longboat Key Homes under $500,000

Welcome to Longboat Key, Florida—a hidden gem along the stunning Gulf Coast. Known for its pristine beaches, vibrant sunsets, and a laid-back atmosphere, Longboat Key is the perfect place for those seeking a tranquil lifestyle without sacrificing access to modern amenities. Nestled just off the coast of Sarasota, this charming island community offers a unique blend of natural beauty and sophisticated living.

For homebuyers looking to make Longboat Key their own, you’ll be delighted to discover that there are beautiful homes available for under $500,000. This is an incredible opportunity to own a piece of paradise without breaking the bank. Whether you’re searching for a cozy beach cottage, a stylish condo with breathtaking ocean views, or a serene retreat surrounded by lush landscaping, Longboat Key has something that will fit your needs and budget.

Imagine waking up each morning to the sound of gentle waves lapping at the shore, or enjoying a leisurely afternoon stroll along the sandy beaches. The community is not only rich in natural beauty but also offers a variety of recreational activities, from boating and fishing to golfing and dining at exquisite local restaurants. With a strong sense of community and a relaxed lifestyle, it's no wonder that Longboat Key is a sought-after destination for families, retirees, and everyone in between.

Don’t miss your chance to explore the charming homes available in this idyllic locale. Longboat Key is waiting to welcome you home!

Newest Longboat Key Homes under $500,000

693 Spanish Drive N Unit 24, Longboat Key image

693 Spanish Drive N Unit 24, Longboat Key $423,750

Spanish Main Yacht Club is a 55+ community. There are 213 villa, ground-level attached condo units in this condo complex. It has a marina with boat docks, a clubhouse, sw...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

738 Spanish Drive S Unit 98, Longboat Key image

738 Spanish Drive S Unit 98, Longboat Key — 738 $495,000

Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With ab...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

2600 Harbourside Drive Unit Q8, Longboat Key image

2600 Harbourside Drive Unit Q8, Longboat Key — Longboat Key Moorings Marina $189,000

**NO LONGBOAT KEY CLUB MEMBERSHIP REQUIRED!** A rare and highly desirable opportunity to own a 48' x 21' deep-water slip at the prestigious Longboat Key Club Moorings wit...

Longboat Key Moorings SubDv.
34228 Zip Code

845 Spanish Drive N Unit 845, Longboat Key image

845 Spanish Drive N Unit 845, Longboat Key — 845 $450,000

Positioned directly across from the marina and boat slips, this updated villa in Spanish Main Yacht Club enjoys beautiful marina views and puts boating and waterfront acc...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

554 Spanish Drive S, Longboat Key — Spanish Main Yacht Club $425,000

Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated ...

2 Beds
2 Baths
Spanish Main Yacht Club SubDv.
34228 Zip Code

600 Sutton Place Unit 101B, Longboat Key image

600 Sutton Place Unit 101B, Longboat Key — 600 $319,000

Waterfront condo with Sarasota Bay views! Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, ...

1 Beds
1 Baths
Sutton Place Condo SubDv.
34228 Zip Code

4380 Exeter Drive Unit 101, Longboat Key image

4380 Exeter Drive Unit 101, Longboat Key — 101 $389,500

Virtually Staged. Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after commu...

2 Beds
2 Baths
Longboat Harbour Towers SubDv.
34228 Zip Code

4485 Gulf Of Mexico Drive Unit 402, Longboat Key image

4485 Gulf Of Mexico Drive Unit 402, Longboat Key — 4485 $456,789 ▼

Virtually Staged. Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #...

2 Beds
2 Baths
Arbomar Apts SubDv.
34228 Zip Code

408 Gulf Of Mexico Drive Unit 2207, Longboat Key image

408 Gulf Of Mexico Drive Unit 2207, Longboat Key — Boathouse On Longboat $49,000

Welcome to Slip #2207 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protec...

Boathouse On Longboat SubDv.
34228 Zip Code

408 Gulf Of Mexico Drive Unit 1206, Longboat Key image

408 Gulf Of Mexico Drive Unit 1206, Longboat Key — Boathouse On Longboat $65,000

Welcome to Slip #1206 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protec...

Boathouse On Longboat SubDv.
34228 Zip Code

408 Gulf Of Mexico Drive Unit 2114, Longboat Key image

408 Gulf Of Mexico Drive Unit 2114, Longboat Key — Boathouse On Lonboat $39,000

Welcome to Slip #2114 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protec...

Boathouse On Longboat 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