Longboat Key, FL Homes under $500,000

Experience the best of waterfront living on beautiful Longboat Key! This light-filled, meticulously maintained 2-bedroom, 2-bath condo offers sweeping views of the harbor on Sarasota Bay, creating a serene backdrop for your beach to bay life style. Located in the sought-after Longboat Harbour community, this residence features an open floor plan, an updated kitchen with modern appliances,

Brett Keyser, Jr RE/MAX ALLIANCE GROUP

Welcome to your dream escape at Longboat Harbour, where breathtaking views of Sarasota Bay and the Intercoastal Waterway await you. Picture yourself stepping outside to enjoy deeded beach access and the convenience of first-come, first-serve boat docks, all within a vibrant community that feels like a vacation every day. In this serene oasis, you can unwind and soak in the beauty of nature,

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

REDUCED PRICE Motivated Seller! Seller will pay up to $10,000 of Buyers closing cost. Great investor or seasonal rental property - This charming turnkey short-term vacation rental one bedroom with two queen size beds, one bath and a queen size sofa sleeper, living-dining combo is a beach side end unit. It comfortably accommodates six individuals for an enjoyable stay. Including a screened in

George Sanchez EZ CHOICE REALTY

First floor walkdown Junior Suite with spectacular views of Longboat Key Club’s Golf Course now available to rent out or enjoy for your own vacation getaway with no hotel program restrictions on owner time. There is an expanded deck in addition to the covered terrace, which is perfect for watching a wide variety of wildlife and golfing activity. Building 5 is positioned where owners value privacy

Ian Addy, PA MICHAEL SAUNDERS & COMPANY

Light and bright, and MOVE-IN READY! Turnkey furnished, Just bring your Flip Flops! Kitchen gutted to studs, totally updated. Tile floors, lots of closet space throughout. Updated baths, enclosed lanai with tile floors and electric shades overlooks lovely water view. Lovely updated décor. Furnishings are negotiable. Longboat Harbour is amenity packed- 4 heated pools, tennis/pickleball, fitness

Michael Yawitz MICHAEL SAUNDERS & COMPANY

OMG! Priced $45,000 under certified appraisal amount. Extra Extra and Extra. That is what you get with this home. Extra big, Extra light and Extra convenient. Bottom floor, End unit, deeded covered parking just outside your door, views of the bay and canal, right next to the pool. This end unit is larger than interior units and has more of a home feeling than a unit feeling. With plentiful back

Dan Feuser PREFERRED SHORE LLC

GULF TO BAY TWIN SHORES BEACH AND MARINA VILLAS. UNBELIEVABLE DIRECT BAYFRONT and MARINA VIEWS! COMPLETELY REMEDIATED AND ASSOCIATION INSURANCE FOR THE 8 VILLAS PAID IT ALL ( 100%). EVERYTHING NEW IN OCTOBER, 2025 FROM SHEETROCK, NEW SPECIAL FLOOD BARRIER SLIDER.($8000) APPLIANCES, UPGRADED NEW CABINETRY, 2 DOORS INCLUDING 4 POCKET DOORS, NEW A/C MINI SPLITS, HOTWATER HEATER, W/D AND LOVELY

Marni Hayden CHROME REALTY LLC

Wow, here's your opportunity to buy the most charming Beach Cottage on the North End of Longboat Key. Maybe considered an original Whitney Cottage, this charming 2-bed 2-bath home is a perfect setting to create your dream beach home. Slightly elevated structure on corner lot with Alley access and peek a boo Bay Views (More to be had if you went up). The essence and spirit are alive with this

Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 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. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota

Jennifer Wilson LBRE LLC

Here is your chance to experience quintessential Coastal Living in the dynamic community of Longboat Harbour located on beautiful Longboat Key. Note: NO Storm Damage! Imagine having your coffee while watching the sunrise from your enclosed lanai in the morning overlooking the water leading to Sarasota Bay, and later in the day, enjoying a private beach area on the Gulf of America with stunningly

David McHugh COLDWELL BANKER REALTY

Welcome to the stunning Sutton Place Condominiums—COMPLETLEY UNTOUCHED BY WATER!Nestled along Sarasota Bay in Longboat Key and just steps from the turquoise waters of the Gulf of Mexico, this community offers an unbeatable location—a true paradise found! Step inside this spacious, ground-floor corner unit and be greeted by an expansive open-concept living space. The remodeled kitchen boasts

Jill Baldwin KW PEACE RIVER PARTNERS

72 ft x 26 ft Boat Slip on L-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline from atop your flybridge. LBK Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes

Jennifer Wilson LBRE LLC

Opportunity now in the Coveted Village of Longboat Key. Steps from the stunning Gulf of Mexico, this property offers an unparalleled chance to immerse yourself in the charm of one of Florida's most unique coastal communities. The existing structure is a solidly built, block-construction home featuring three bedrooms (only 2 on tax roll), two bathrooms, and approximately 1,200 square feet of

Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

Your Exclusive Ticket to the Ultimate Beach & Boating Lifestyle! This move-in ready fully furnished gem on Longboat Key is more than just a home—it’s a lifestyle upgrade for those who crave adventure, relaxation, and social connection. Wake up to breathtaking bay views from your condo, complete with granite countertops, updated appliances, and an upgraded spa-like shower. Enjoy private beach

Rachel Rademacher HOUSE MATCH

This chic designer two-bedroom townhome is simply gorgeous throughout. Offered furnished and ready to move into. Each room has received a thoughtful and elegant design, from furnishings to color schemes. The first floor is beautifully tiled with many updates including the kitchen with Quartz counters and backsplash, custom cabinetry, custom sink and faucet, and convenient washing machine. Baths

Michael Yawitz MICHAEL SAUNDERS & COMPANY

SPECTACULAR FULL SARASOTA BAY VIEW. Well-maintained, Move-In Ready one bedroom in a premium A building with NO storm damage ! Relax and enjoy coastal living on the enclosed lanai, while watching the sunrise, the beautiful panoramic Harbour water view , dolphins , manatees and birds shows. The community is boater friendly with boat slips that will accommodate a sailboat or power boat up to 34 ft

Malihe Karimi MICHAEL SAUNDERS & COMPANY

New Large Price Improvement! Now the absolute best buy for Vacant Land on all of Longboat Key. An exceptional vacant lot is now available in the coveted North End of Longboat Key. LARGE LOT at 8,400 square feet, this prime property provides the perfect canvas to build your dream home on this exclusive island. With PRIVATE, DEEDED and GATED Beach access, you'll enjoy the serene Gulf waters and

Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

PRICE ADJUSTMENT on this very special loft style condominium with 1 bedroom and 1.5 baths with a unique contemporary flair, coming furnished with some exclusions. Beautiful tile flooring throughout the main living area and designer carpeting on the stairs and bedroom. The stainless steel appliances and air conditioner are all new. Located on Longboat Key in the lovely Seaplace community which has

Sandra Endres COLDWELL BANKER REALTY

Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover

Simone Schaerf MICHAEL SAUNDERS & COMPANY

This beautiful corner unit is in excellent condition and has not experienced any storm damage, offering peace of mind for potential buyers. Additionally, being a two-story complex, association will not incur unexpected costs from new Milestone inspections providing buyers with one of the lowest quarterly fees on the island. Located just across the street from the turquoise, uncrowded public

Edward Campbell MICHAEL SAUNDERS & COMPANY

70 x 21 Boat Slip on R-dock at Longboat Key Moorings Marina for sale. This is a great slip with exceptional views of Sarasota Bay and the city skyline. Easy in/out boat access too. LBK Club membership is optional. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village

Jennifer Wilson LBRE LLC

72' x 21' Boat Dock ~ The Only TWO Level Boat Dock in the Marina AND This Dock has NO COVENANT SO THERE IS NO Membership Requirement to join The Longboat Key Club when you purchase the slip. Longboat Key Moorings is strategically located on the beautiful exclusive island of Longboat Key ~ just a few minutes to St. Armands Circle ~ downtown Sarasota or Bradenton Beach. This amazing location

Rian Carver FINE PROPERTIES