Longboat Key Homes with Two Story Property Description

Welcome to Longboat Key, a picturesque barrier island located in the sunny state of Florida. Known for its pristine beaches, upscale dining, and world-class golf courses, Longboat Key offers a luxurious yet laid-back lifestyle for residents and visitors alike.

If you're in the market for a two-story home in Longboat Key, you're in luck! With a variety of architectural styles and designs to choose from, you'll find the perfect property to suit your needs. Whether you're looking for a cozy beach cottage or a spacious waterfront estate, Longboat Key has something for everyone.

Imagine waking up to stunning water views from your second-story bedroom, or enjoying a sunset cocktail on your private balcony overlooking the Gulf of Mexico. With a two-story home in Longboat Key, the possibilities are endless.

Experience the best of coastal living in Longboat Key, where you can enjoy the tranquility of island life while still being just a short drive away from the vibrant city of Sarasota. Don't miss out on the opportunity to own a piece of paradise in this charming seaside community.

Newest Longboat Key Homes with Two Story Property Description

3100 Gulf Of Mexico Drive, Longboat Key image

3100 Gulf Of Mexico Drive, Longboat Key $5,295,000

Set against the luminous backdrop of prestigious Longboat Key, this newly built residence offers a quietly sophisticated interpretation of island living. Ideally situated...

5 Beds
5 Baths
Triton Cove SubDv.
34228 Zip Code

3617 Fair Oaks Place, Longboat Key image

3617 Fair Oaks Place, Longboat Key $2,100,000

Virtually Staged. Tucked within the highly sought after Queens Harbour enclave of Bay Isles, this exceptional residence captures the effortless elegance and relaxed sophi...

3 Beds
4 Baths
Queens Harbour (F/K/A Manchester Bay) SubDv.
34228 Zip Code

3360 Bayou Sound, Longboat Key $4,699,999

Virtually Staged. Brand-new custom construction in Bay Isles? This is it. Introducing an exceptional new residence in one of Longboat Key’s most coveted gated communities...

5 Beds
5 Baths
Bay Isles SubDv.
34228 Zip Code

3578 Fair Oaks Way, Longboat Key $2,695,000

Waterfront living takes center stage at this impressive Queens Harbour residence, offering 3 bedrooms plus a den and 3½ bathrooms across more than 3,000 square feet of in...

3 Beds
4 Baths
Queens Harbour (F/K/A Manchester 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

560 Chipping Lane, Longboat Key $3,999,990

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible li...

5 Beds
5 Baths
Country Club Shores SubDv.
34228 Zip Code

3530 Mistletoe Lane, Longboat Key $2,675,000

Freshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront residence in guard-gated Corey’s Landing returns to the market with significant interi...

4 Beds
4 Baths
Coreys Landing SubDv.
34228 Zip Code

3453 Gulf Of Mexico Drive Unit 200, Longboat Key image

3453 Gulf Of Mexico Drive Unit 200, Longboat Key — 3453 $390,000

TURNKEY BEACHFRONT LIVING WITH EXCEPTIONAL RENTAL FLEXIBILITY ON LONGBOAT KEY! Located at Sea Horse Beach Resort, this spacious 1-bedroom, 1-bath condominium offers 876 s...

1 Beds
1 Baths
Sea Horse Beach Resort SubDv.
34228 Zip Code

711 Old Compass Road, Longboat Key image

711 Old Compass Road, Longboat Key $6,495,000 ▼

This spectacular waterfront pool home was just completed in 2026 and is built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired resi...

4 Beds
6 Baths
Emerald Harbor SubDv.
34228 Zip Code

657 Halyard Lane, Longboat Key $4,300,000

Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboa...

4 Beds
5 Baths
Country Club Shores SubDv.
34228 Zip Code

626 Buttonwood Drive, Longboat Key image

626 Buttonwood Drive, Longboat Key $4,395,000 ▼

Private Marina. Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfe...

6 Beds
6 Baths
Longboat Shores SubDv.
34228 Zip Code

7143 La Lenaire Drive, Longboat Key image

7143 La Lenaire Drive, Longboat Key $5,895,000 ▼

Private island home for sale on Jewfish Key, Longboat Key, Florida. This 4-bedroom, 4-bath waterfront residence sits on a 1.24-acre titled lot with approximately 300 feet...

4 Beds
4 Baths
La Lenaire Isle SubDv.
34228 Zip Code