Longboat Key, FL Homes for Sale with Pool

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  /75

  $13,995,000

  New Construction $1M PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 6,616 Sq Ft

  6489 Gulfside Rd, Longboat Key, FL 34228

  This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and

  Nicholle McKiernan COLDWELL BANKER REALTY

  6489 Gulfside Rd, Longboat Key, FL 34228
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  /34

  $499,000

  $116K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  5231 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location,

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  5231 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  /18

  $410,000

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228

  Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and

  Brooke Moran DALTON WADE INC

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228
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  /47

  $1,025,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  240 Sands Point Rd Unit 4104, Longboat Key, FL 34228

  Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  240 Sands Point Rd Unit 4104, Longboat Key, FL 34228
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  /28

  $515,000

  • 2 Beds
  • 2 Baths
  • 933 Sq Ft

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Assigned parking space is 590. I have "hurricane-impact doors & windows".

  Stephen Hachey FLAT FEE MLS REALTY

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  /66

  $599,900

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  848 Evergreen Way, Longboat Key, FL 34228

  Turn-Key Furnished Waterfront Townhome in Cedars East on Longboat Key! Beautifully updated and move-in ready, this desirable 2-bedroom, 2.5-bath residence offers one of the best locations within Cedars East, featuring tranquil water views from the spacious primary suite and an expanded, open-concept living area. The updated kitchen showcases shaker-style cabinetry, granite countertops, stainless

  Rex Glasson DOUGLAS ELLIMAN

  848 Evergreen Way, Longboat Key, FL 34228
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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
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  /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
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  /62

  $1,000,000

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

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

  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 skies each evening. Situated

  Steve Nursey MICHAEL SAUNDERS & COMPANY

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

  $599,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

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

  Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully

  Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /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
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  /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
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  /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
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  /25

  $150,000

  $9K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  3710 Gulf of Mexico Dr Unit D19, Longboat Key, FL 34228

  FANTASTIC OPPORTUNITY to own a home in a beach-to-bay community. Gulfshore of Longboat Key has it all -- private, pristine sand beach, on the Gulf of Mexico, a marina (needs to be repaired) on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the

  Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  3710 Gulf of Mexico Dr Unit D19, Longboat Key, FL 34228
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  /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
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  /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
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  /91

  $800,000

  Open Sun 1PM - 4PM $185K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  2326 Harbour Oaks Dr, Longboat Key, FL 34228

  PRICE IMPROVEMENT – REDUCED $99,000! Discover refined coastal living in this impeccably maintained, fully furnished end-unit villa on Longboat Key, now offered at an exceptional new value following a $99,000 price reduction. Offering nearly 2,400 square feet of thoughtfully designed living space, this residence combines the privacy and feel of a single-family home with the ease of

  Rachel Tritschler RE/MAX ALLIANCE GROUP

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

  $754,900

  $40K 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
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  /41

  $2,350,000

  $145K PRICE DROP

  • 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
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  /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
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  /69

  $750,000

  • 2 Beds
  • 2 Baths
  • 1,423 Sq Ft

  900 Spanish Dr N, Longboat Key, FL 34228

  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 Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your

  Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  900 Spanish Dr N, Longboat Key, FL 34228
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  /83

  $4,999,000

  • 5 Beds
  • 3 Baths
  • 3,842 Sq Ft

  3606 Fair Oaks Place, Longboat Key, FL 34228

  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 of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  3606 Fair Oaks Place, Longboat Key, FL 34228
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  /55

  $1,245,000

  $254K 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
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  /52

  $724,900

  Open Sat 11AM - 2PM $104K 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
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  /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
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  /99

  $649,900

  $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
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  /21

  $7,299,000

  New Construction $100K PRICE DROP

  • 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
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  /24

  $6,995,000

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 4,776 Sq Ft

  7094 Longboat Dr E, Longboat Key, FL 34228

  Pre-Construction. To be built. An extraordinary opportunity to create a world-class waterfront estate on Sarasota Bay, this stunning new construction residence offers the ultimate blend of luxury, craftsmanship, and coastal living in one of Sarasota’s most coveted locations. Situated on an expansive 11,000+ square foot bayfront homesite, this magnificent two-story design features six spacious

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  7094 Longboat Dr E, Longboat Key, FL 34228
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  /26

  $1,199,000

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

  2301 Gulf of Mexico Dr Unit 33, Longboat Key, FL 34228

  Experience breathtaking beachfront living in this rare direct Gulf-front residence at the prestigious Islander Club on Longboat Key. This two-bedroom, two-bath condominium showcases panoramic Gulf of Mexico views from every room, including the living room, primary suite and guest bedroom, creating a spectacular coastal backdrop throughout the home. One of the exceptional features of this

  Chris Wetzig PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2301 Gulf of Mexico Dr Unit 33, Longboat Key, FL 34228
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  /32

  $799,000

  $100K 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
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  /91

  $2,550,000

  • 4 Beds
  • 4.5 Baths
  • 4,154 Sq Ft

  3527 Fair Oaks Ln, Longboat Key, FL 34228

  Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent

  Miriam Pearson COLDWELL BANKER REALTY

  3527 Fair Oaks Ln, Longboat Key, FL 34228
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  /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
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  /44

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,513 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
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  /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

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