352

Longboat Key, FL Homes for Sale with AC

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  • /43

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,362 Sq Ft

    3330 Gulf of Mexico Dr Unit 107D, Longboat Key, FL 34228

    Island Elegance on the Bay: A Turnkey Waterfront Sanctuary! Escape to the serene shores of Longboat Key and experience the pinnacle of coastal luxury at 3330 Gulf of Mexico Drive. This meticulously reimagined, two-bedroom, two-bathroom residence offers a rare "walk-out" lifestyle, where lush green lawns meet the shimmering waters of the Sarasota Bay. The Interior: Modern Luxury Meets Tropical

    Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

    3330 Gulf of Mexico Dr Unit 107D, Longboat Key, FL 34228
  • /54

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,014 Sq Ft

    5310 Gulf of Mexico Dr Unit 16, Longboat Key, FL 34228

    Turnkey-Furnished Longboat Key Condo with Dock Access & Short-Term Rental PotentialExperience the best of coastal living in this beautifully furnished turnkey condo on highly sought-after Longboat Key. Perfect as a personal getaway or an income-producing investment, this residence is one of the rare properties that allows short-term rentals, giving you exceptional flexibility and earning

    Miguel Rosa WAGNER REALTY

    5310 Gulf of Mexico Dr Unit 16, Longboat Key, FL 34228
  • /67

    $2,890,000

    $310K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,525 Sq Ft

    435 L Ambiance Dr Unit L707, Longboat Key, FL 34228

    There are views... and then there is this view! From this desirable seventh-floor corner residence at L’Ambiance, the horizon unfolds in a breathtaking panorama—Gulf of Mexico sunsets ablaze to the west, Sarasota Bay shimmering to the east, the downtown skyline sparkling in the distance, and the manicured fairways of the Longboat Key Club Island side golf course below. Morning light and evening

    Pam Charron COMPASS FLORIDA LLC

    435 L Ambiance Dr Unit L707, Longboat Key, FL 34228
  • /38

    $3,150,000

    • 3 Beds
    • 5.5 Baths
    • 3,666 Sq Ft

    3620 Fair Oaks Place, Longboat Key, FL 34228

    Come for a visit and you will want to stay and make it yours! Strategically set back from the road, and appropriately positioned on this oversized lot, to allow for an abundance of private waterfront splendor. The expansive paver patio, with oversized pool, spa, outdoor kitchen, and fully equipped pool bath make this the prime setting for endless entertainment and fun with family and friends. Bay

    Cindy Schatzle COLDWELL BANKER REALTY

    3620 Fair Oaks Place, Longboat Key, FL 34228
  • /62

    $1,000,000

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft

    2301 Gulf of Mexico Dr Unit 43, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset

    Steve Nursey MICHAEL SAUNDERS & COMPANY

    2301 Gulf of Mexico Dr Unit 43, Longboat Key, FL 34228
  • /59

    $599,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

    Welcome to elevated beachfront living in highly desirable Windward Bay — a premier bayside enclave offering serene coastal charm and resort-style amenities on picturesque Sarasota Bay. This fully reimagined 2-bedroom, 2-bath villa has been thoughtfully renovated from top to bottom with impeccable attention to detail and contemporary finishes throughout. Step inside to discover an open,

    Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
  • /40

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,110 Sq Ft

    5311 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

    Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior

    Roger Pettingell COLDWELL BANKER REALTY

    5311 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
  • /22

    $749,900

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft

    4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228

    Waterfront Living on Longboat Key – Direct Gulf AccessExperience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact

    Toni Giliberti COLDWELL BANKER REALTY

    4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228
  • /37

    $960,000

    • 1 Bed
    • 1 Bath
    • 634 Sq Ft

    250 Sands Point Rd Unit 5106, Longboat Key, FL 34228

    Completely renovated first floor walkdown Junior Suite with spectacular views of Longboat Key Club’s Golf Course currently in the hotel program now available. There is an expanded deck in addition to the covered terrace, ideal for watching a wide variety of wildlife and golfing activity. Building 5 is positioned where owners value privacy from the hustle and bustle of the main entrance and pool

    Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    250 Sands Point Rd Unit 5106, Longboat Key, FL 34228
  • /33

    $2,345,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,314 Sq Ft

    340 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

    Your Longboat Key oasis awaits! This totally renovated 3bdrm 2.5 bath condo offers a open concept living space with high ceilings and walls of glass allowing sweeping views os Sarasota Bay. Light and bright material selections mix modern luxury with a coastal theme.The gourmet kitchen features white soft close custom cabinetry, sleek glass doors, quartz countertops, mother of pearl

    Reid Murphy DEVELOPERS REALTY LBK, INC

    340 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
  • /39

    $799,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft

    5655 Gulf of Mexico Dr Unit D107, Longboat Key, FL 34228

    Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the

    John Milkovich CHARLES RUTENBERG REALTY INC

    5655 Gulf of Mexico Dr Unit D107, Longboat Key, FL 34228
  • /91

    $915,000

    Open Tue 1PM - 4PM $70K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    2326 Harbour Oaks Dr, Longboat Key, FL 34228

    A rarely available END UNIT villa is located on Longboat Key within the gated Bay Isles community, offering the opportunity to embrace true island living with expansive private terrace space and tranquil pond views fed by the saltwater bay. Encompassing nearly 2,400 square feet of thoughtfully designed interiors, this residence delivers privacy, security, and effortless elegance in one of

    Rachel Tritschler RE/MAX ALLIANCE GROUP

    2326 Harbour Oaks Dr, Longboat Key, FL 34228
  • /61

    $774,900

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,460 Sq Ft

    5270 Gulf of Mexico Dr Unit 508, Longboat Key, FL 34228

    Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of

    Beth Ann Boyer MICHAEL SAUNDERS & COMPANY

    5270 Gulf of Mexico Dr Unit 508, Longboat Key, FL 34228
  • /41

    $2,495,000

    • 3 Beds
    • 2 Baths
    • 1,972 Sq Ft

    617 Rountree Dr, Longboat Key, FL 34228

    Premier waterfront opportunity in Longboat Key Estates, offering direct canal frontage in one of the island’s most desirable residential enclaves.Positioned along a quiet interior street, this property offers the opportunity to own or build a custom coastal residence in an area undergoing continued redevelopment and investment potential. Surrounding properties reflect the neighborhood's

    Judi Taulbee FINE PROPERTIES

    617 Rountree Dr, Longboat Key, FL 34228
  • /57

    $1,749,500

    $300K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 2,823 Sq Ft

    5920 Gulf of Mexico Dr, Longboat Key, FL 34228

    DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place.

    John Donato JOHN DONATO REAL ESTATE INC

    5920 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /55

    $1,299,000

    $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft

    3010 Grand Bay Blvd Unit 432, Longboat Key, FL 34228

    Step into the foyer from your private elevator and through chic double doors into this fully furnished Grand Bay masterpiece where drama meets elegance. Floor-to-ceiling glass sliders reveal a breathtaking panorama of the downtown city skyline, John Ringling Bridge, Harbourside golf course, and Sarasota Bay. The open floor plan seamlessly connects the living and dining areas to a versatile

    Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    3010 Grand Bay Blvd Unit 432, Longboat Key, FL 34228
  • /52

    $774,900

    $54K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    4725 Gulf of Mexico Dr Unit 314, Longboat Key, FL 34228

    Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A

    Michael Albano, PA COLDWELL BANKER REALTY

    4725 Gulf of Mexico Dr Unit 314, Longboat Key, FL 34228
  • /45

    $1,395,000

    • 2 Beds
    • 2 Baths
    • 1,503 Sq Ft

    1145 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

    Welcome to Beachplace #1-503, a coveted fifth-floor direct Gulf-front getaway in Building 1, offering panoramic beach and Gulf views from one of Longboat Key’s most desirable waterfront communities. Encompassing 1,503 square feet of interior living space, this two-bedroom, two-bath residence delivers front-row access to turquoise waters and spectacular sunset skies.Extensively updated, this

    Roger Pettingell COLDWELL BANKER REALTY

    1145 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228
  • /50

    $1,775,000

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,298 Sq Ft

    340 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

    Perfectly positioned on Sarasota Bay at the southern end of Longboat Key, this beautifully renovated 3BR/3BA, 2,298± sq. ft. residence with a private 2-car garage at Tangerine Bay Club combines luxury, comfort, and a premier location just moments from St. Armands Circle and downtown Sarasota. A private front courtyard welcomes you inside, where rich wood floors, custom doors, and neutral tones

    Bruce Myer COLDWELL BANKER REALTY

    340 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228
  • /99

    $649,900

    Open Sun 1PM - 3PM $79K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    4310 Falmouth Dr Unit 102, Longboat Key, FL 34228

    Recently reduced—don’t miss this opportunity. No special assessments after the 2024 storms, no history of flooding, well-funded reserves, and structural soundness supported by SIRS report! Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and

    Kerre Allman MARCUS & COMPANY REALTY

    4310 Falmouth Dr Unit 102, Longboat Key, FL 34228
  • /21

    $7,399,000

    New Construction
    • 5 Beds
    • 7 Baths
    • 4,452 Sq Ft

    591 Golf Links Ln, Longboat Key, FL 34228

    Pre-Construction. To be built. Wake up to shimmering views, spend your afternoons on the water, and end your evenings watching the Sarasota skyline glow from your private rooftop deck. This is the kind of home that defines the Longboat Key lifestyle. To be built by Brista Homes and designed by Mark Sultana of DSDG Architects, this stunning residence is set on one of the largest canal-front lots

    Gina Ursini BRISTA REALTY LLC

    591 Golf Links Ln, Longboat Key, FL 34228
  • /39

    $470,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    4370 Chatham Dr Unit 104, Longboat Key, FL 34228

    Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation

    Sharon Meier PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4370 Chatham Dr Unit 104, Longboat Key, FL 34228
  • /73

    $689,000

    Open Sat 1PM - 3PM $86K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    4900 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment

    Debby McCaig COLDWELL BANKER REALTY

    4900 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • /43

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,287 Sq Ft

    6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228

    Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer

    Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

    6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228
  • /85

    $2,400,000

    • 3 Beds
    • 3.5 Baths
    • 3,192 Sq Ft

    3610 Bayou Cir, Longboat Key, FL 34228

    Welcome to The Bayou section of beautiful Bay Isles. Tucked away from the hustle and bustle of daily life, this double-gated community, a collection of 126 homes, is the perfect place to be on Longboat Key. The pavered front circular drive delivers you to the elevated double-door entrance. Step inside and prepare to be delighted by the neutral palate throughout and an abundance of natural light.

    Mike Prisco MICHAEL SAUNDERS & COMPANY

    3610 Bayou Cir, Longboat Key, FL 34228
  • /50

    $2,149,000

    Open Tue 1PM - 4PM $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,311 Sq Ft

    500 Halyard Ln, Longboat Key, FL 34228

    Gorgeous Views - Impact Windows & Doors - 1/2 Acre Elevated Lot - Enjoy the Longboat Key Island Lifestyle - In a prime South Longboat Key location, this beautifully updated waterfront home offers a blend of privacy, comfort and exceptional boating access. Set on a large, elevated, tropically landscaped lot, the property captures wide water canal views stretching toward Sarasota Bay, with stunning

    Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

    500 Halyard Ln, Longboat Key, FL 34228
  • /32

    $839,900

    $59K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft

    4825 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

    Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact

    JoDene Moneuse MICHAEL SAUNDERS & COMPANY

    4825 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
  • /82

    $750,000

    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft

    925 Spanish Dr N Unit 60, Longboat Key, FL 34228

    Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The

    Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

    925 Spanish Dr N Unit 60, Longboat Key, FL 34228
  • /26

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    4440 Exeter Dr Unit 106, Longboat Key, FL 34228

    Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway.Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed

    Roger Richmond KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    4440 Exeter Dr Unit 106, Longboat Key, FL 34228
  • /44

    $1,595,000

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft

    2425 Gulf of Mexico Dr Unit 1A, Longboat Key, FL 34228

    This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're

    Robert Delaney MICHAEL SAUNDERS & COMPANY

    2425 Gulf of Mexico Dr Unit 1A, Longboat Key, FL 34228
  • /34

    $1,095,000

    • 2 Beds
    • 2 Baths
    • 1,239 Sq Ft

    4311 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

    Some Photo's are virtually staged ! Spectacular gulf front views from this 5th floor 2 bedroom/ 2 bathroom condo residence in rarely available Longboat Beach House with convenient mid key location in close proximity to Longboat Key shops & restaurants as well as Bayfront Park with its pickleball courts and kayak launch and St Armands Circle. Left entirely unscathed by the recent storms, this unit

    Richard Perlman MICHAEL SAUNDERS & COMPANY

    4311 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228
  • /77

    $5,495,000

    New Construction $255K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 3,737 Sq Ft

    524 Halyard Ln, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides

    Rob Hunt, Jr HUNT BROTHERS REALTY, INC.

    524 Halyard Ln, Longboat Key, FL 34228

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