Longboat Key Homes with a Pool for Sale

This stunning Gulf front gated Estate property boasts a beautifully almost one acre landscaped setting with a long, elegant paver driveway leading to a spacious six-bedro...

Some of the World’s Most Desirable Addresses Aren’t Reached by Road. There is an unmistakable distinction between owning a beautiful waterfront home and owning a private ...

An Extraordinary Gulf-Front Homesite on North Longboat Key. Imagine dolphins dancing in the turquoise waters as the sun sets in a magnificent display of color. Sit with y...

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...

Introducing a rare legacy estate defined by architectural distinction, extraordinary waterfront, and an exceptional sense of privacy. 6610 Gulf of Mexico Drive is the pin...

Nestled on the coveted north end of Longboat Key, this exceptional residence is tucked away on the secluded and private Lands End Drive, one of the island's most treasure...

Behind the gates of the Longboat Key Club in the highly coveted Corey’s Landing neighborhood, this free-standing home with direct open Bay views enjoys a private pool and...

Behind the double-gated entry of Bay Isles’ coveted Harbor section, 560 Harbor Point commands a rare position at the end of a quiet cul-de-sac, with 200 feet of pristine,...

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

Beyond the gates of Bayou Hammock, where just 13 residences share one of north Longboat Key’s most private waterfront settings, a true coastal retreat awaits. Arrive thro...

MODERN BEACH LUXURY | OCEAN VIEWS | PRIVATE BOAT DOCK & LIFT | LAGUNA YACHT VILLAGE Aggressively Priced for a Motivated Sale — Owners Relocating! Discover an extraordi...

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

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...

Ideally situated at the north end of Longboat Key within the confines of The Preserve of Longbeach rests this stunning modern coastal residence. The tastemaker’s tastemak...

This stunning, elevated coastal home is the epitome of luxurious island living. A waterfront paradise offering dreamy views from multiple rooms. From the moment you arriv...

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

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...

Pre-Construction. To be built. To be built. Brought to you by Noah Thomas Builders - Best in Luxury Coastal. This stunning new construction home at 592 Juan Anasco Dr off...

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...

Virtually Staged. Welcome to an extraordinary waterfront estate on coveted Longboat Key, where timeless coastal elegance meets world-class boating. Perfectly situated on ...

Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front hom...

Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence ...

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...

Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attent...

Expect luxury living and a world of conveniences within the serene enclave of Buttonwood Harbour on Longboat Key, where care and impeccable style converge in this 3BR/3BA...

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

Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend ...

This beautifully reimagined John Cannon home, in the tranquil north end of Longboat Key, blends luxury with island living. The custom, Spanish-style design offers four be...

Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gat...

Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers...

Escape to your own waterfront haven at 617 Rountree Drive, a hidden gem nestled in the luxurious Longboat Key Estates community! Tucked away on a tranquil street, this 3-...

Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access ac...

Tucked along one of the most sought-after canals in Country Club Shores, 524 Hornblower Lane is a waterfront residence that fully embodies the Longboat Key lifestyle, whe...

Pre-Construction. To be built. Positioned directly across from the iconic St. Regis Longboat Key Resort, this exceptional waterfront residence offers immediate access to ...

Pre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Longboat Key. This exquisite residence boasts 4 bedrooms and 4.5 bathrooms across ...

This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated F...

PRIVATE HEATED POOL | DEEDED GULF BEACH ACCESS | FULLY FURNISHED Enjoy the Longboat Key lifestyle in this beautifully furnished 3-bedroom, 3.5-bath villa in gated Bay ...

Boaters will love this spacious elevated home in a premier waterfront location on Longboat Key with dock, lift and by boat it is just four homes from the intercoastal, op...

A few photos virtually staged. Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professi...

Under Construction. PRE-AUCTION: Bidder registration deadline: 5 November. Rising on nearly two private Gulf-front acres, this visionary estate is poised to become one o...

Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this b...

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's mos...

GORGEOUS COMPLETELY REMODELED Villa with Lake Views in Spanish Main Yacht Club!! Welcome to effortless coastal living in this beautifully remodeled 3-bedroom, 2-bath vil...

Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary 2.4 acre, fully gated coastal estate that b...

THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking col...

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor...

Ready to live directly on the Gulf? This Seaward Homes Curated Collection residence at 6489 Gulfside is move-in ready, with direct Gulf-front private access and stunning ...

Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Sho...

Virtually Staged. Under Construction. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat K...

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat...