Longboat Key, FL Homes

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  /30

  $1,874,000

  • 2 Beds
  • 2 Baths
  • 1,827 Sq Ft

  1211 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

  Surround yourself with captivating views and timeless design in this coastal retreat thoughtfully renovated by Brista Homes. While offering partial views, this residence is the closest unit on the market to full beachfront—just one tier away—making it a rare opportunity to enjoy a front-row coastal lifestyle. Inside, every detail has been thoughtfully curated to inspire both beauty and function.

  Gina Ursini BRISTA REALTY LLC

  1211 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
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  /42

  $3,400 per month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228

  2 Bd/2 Bath on Sarasota Bay Across from Gulf of Mexico - Three to seven-month rental beginning June 1st.Beautiful corner unit condo with an abundance of windows located between Sarasota Bay and across the street from the deeded Gulf of Mexico beach. The gated community complex has every amenity imaginable - four pools, tennis court, shuffleboard, kayak launch, and golf putting range. When

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228
• 

  

  /2

  $555,000 Sold Jun 03, 2025

  • 1,192 Sq Ft
  • $466/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2016 Harbourside Dr Unit 332, Longboat Key, FL 34228

  A Must-See Full View of Sarasota Bay!Welcome to 2016 Harbourside Drive, Unit #332—a true gem offering breathtaking, unobstructed views of Sarasota Bay from your private balcony. This beautifully updated 2-bedroom, 2-bathroom condo is designed for comfort, style, and easy living. Enjoy the elegance of porcelain tile flooring throughout (no carpet), complemented by stainless steel appliances,

  Francis Perdisatt PREFERRED SHORE LLC

  2016 Harbourside Dr Unit 332, Longboat Key, FL 34228
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  /66

  Est $3,471,172 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 3,687 Sq Ft

  3521 Bayou Pointe, Longboat Key, FL 34228

  3521 Bayou Pointe, Longboat Key, FL 34228
• 

  

  

  /42

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 2,675 Sq Ft

  3318 Bayou Sound, Longboat Key, FL 34228

  Immerse yourself in the timeless charm of West Indies-style living with this extraordinary residence, now offered in the coveted Bayou neighborhood, located behind the exclusive gates in the Bay Isles Community. Combining timeless finishes, thoughtful updates, and unparalleled value, this home is a rare opportunity to own a piece of island-inspired paradise. Even better, this home had no damage

  Nicholle McKiernan COLDWELL BANKER REALTY

  3318 Bayou Sound, Longboat Key, FL 34228
• 

  

  /13

  $4,450 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  640 Broadway St, Longboat Key, FL 34228

  Hurricane rebuild completed in 2025. Discover tranquility and comfort at our serene 3-bedroom, 2-bath home, nestled among lush tropical foliage on a peaceful corner lot in Longboat Key. Inside, experience a welcoming open floor plan with a brand-new living room, modern kitchen, and clean-cut updated bathrooms. Master bedroom features wet bar with mini fridge & windowed ensuite bath. The backyard

  Keith Gordon GETMOREOFFERS

  640 Broadway St, Longboat Key, FL 34228
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  /2

  $740,000 Sold Jun 03, 2025

  • 1,150 Sq Ft
  • $643/SF
  • 78 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4234 Gulf of Mexico Dr Unit H2, Longboat Key, FL 34228

  This stunning 2-bedroom, 2-bath villa in the highly desirable Pelican Harbour community on Longboat Key is the epitome of coastal luxury. Located on the second floor, the residence has been completely renovated with top-of-the-line finishes, including impact windows and doors for added safety and energy efficiency. The open floor plan maximizes the space, allowing natural light to flood the home

  Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  4234 Gulf of Mexico Dr Unit H2, Longboat Key, FL 34228
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  /60

  Est $1,640,102 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft

  2425 Gulf of Mexico Dr Unit 13A, Longboat Key, FL 34228

  2425 Gulf of Mexico Dr Unit 13A, Longboat Key, FL 34228
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  /46

  $1,550,000

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

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228

  Islander Club of Longboat Key - Savor the full, direct Gulf views in this elegantly appointed beachfront condo. This fifth-floor residence in the North Tower boasts majestic west /southwest views of the beach and has been extensively renovated “down-to-the-studs,” including all new electrical and plumbing. A masterfully designed island retreat, the condo features an open layout ideal for

  Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228
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  /60

  $6,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  535 Forest Way, Longboat Key, FL 34228

  Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step into

  Andy Moore GULF COAST REALTY & MANAGEMENT

  535 Forest Way, Longboat Key, FL 34228
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  /2

  $1,750,000 Sold Jun 02, 2025

  • 3,200 Sq Ft
  • $547/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1995

  3303 Sabal Cove Cir, Longboat Key, FL 34228

  New roof, two new HVACs, newly painted exterior, new screened pool enclosure. Discover an exceptional blend of elegance and luxury in this welcoming home, in the exclusive gated community of Bay Isles in Longboat Key. Meticulously maintained and thoughtfully designed, this home has high ceilings, expansive living spaces, and premium finishes throughout. The home surrounds the pool and the lanai,

  Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3303 Sabal Cove Cir, Longboat Key, FL 34228
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  /50

  Est $1,567,355 Not Listed For Sale

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

  2425 Gulf of Mexico Dr Unit 11E, Longboat Key, FL 34228

  2425 Gulf of Mexico Dr Unit 11E, Longboat Key, FL 34228
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  /52

  $975,000

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228

  Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228
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  /17

  $3,450 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  Unlisted Address

  Merging classic elegance with modern luxury featuring high vaulted ceilings, a state-of-the-art kitchen, high-speed internet, and a cutting-edge reverse osmosis water system. Enjoy the convenience of an in-closet washer/dryer and UV air filtration for pristine air quality. Perfect for romantic getaways or peaceful solitude, with boat parking & public launch nearby. The property offers a furnished

  Keith Gordon GETMOREOFFERS

  Unlisted Address
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  /2

  $1,900,000 Sold May 30, 2025

  • 1,819 Sq Ft
  • $1045/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  1045 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  Seller is accepting Back Up Offers. This beachfront 3 bedroom corner residence checks all of the boxes! The azure gulf water is seen through Hurricane Impact Sliders/Windows from almost every room and provides the perfect backdrop for entertaining or simply relaxing on the wraparound terrace with a book enjoying the breeze and watching the sunset. The open kitchen offers state-of-the-art GE

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  1045 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
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  /36

  Est $1,054,217 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  230 Sands Point Rd Unit 3605, Longboat Key, FL 34228

  230 Sands Point Rd Unit 3605, Longboat Key, FL 34228
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  /84

  $3,995,000

  • 5 Beds
  • 5.5 Baths
  • 4,244 Sq Ft

  550 Yardarm Ln, Longboat Key, FL 34228

  NEW PRICE Welcome home to 550 Yardarm Lane, where the beauty of Longboat Key meets the comfort of coastal living in the prestigious Country Club Shores. This warm and inviting WATERFRONT ELEVATED retreat is perfectly designed for those who cherish the Florida lifestyle—complete with gorgeous water views, boating right from your backyard, and plenty of space to relax and entertain. This

  Melanie Russell QUEST PROPERTIES INC

  550 Yardarm Ln, Longboat Key, FL 34228
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  /18

  $9,850 per month

  • 2 Beds
  • 2 Baths
  • 2,331 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private

  Keith Gordon GETMOREOFFERS

  701 Broadway St, Longboat Key, FL 34228
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  /2

  $725,000 Sold May 30, 2025

  • 2,352 Sq Ft
  • $308/SF
  • 135 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  2203 Harbourside Dr, Longboat Key, FL 34228

  Nestled within the exclusive gated enclave of Bay Isles on Longboat Key, this pristine Harbour Oaks villa offers a rare opportunity to experience unparalleled privacy and tranquility in one of Florida's most coveted Gulf Coast communities. With its serene, resort-like atmosphere, the villa promises a lifestyle of luxury and comfort in a setting that defines elegance.Upon entering, you’ll be

  Becky Sirigotis COMPASS FLORIDA LLC

  2203 Harbourside Dr, Longboat Key, FL 34228
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  /79

  Est $5,826,097 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,225 Sq Ft

  1241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
• 

  

  /23

  $849,999

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228

  Ever dreamed of having the beach as both your front and backyard? This beautifully appointed, turnkey-furnished 2-bedroom, 2-bath condo brings that dream to life with views of the Gulf of Mexico and soft sands outside your door. The thoughtfully designed coastal interior combines charm and functionality, featuring an office, updated bathrooms, and a spacious primary suite where you'll wake up to

  Gina Ursini BRISTA REALTY LLC

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228
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  /57

  $10,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,490 Sq Ft
  • Condo for Rent

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228

  Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a

  Maureen Plichta STRINGER MANAGEMENT INC

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
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  /2

  $2,000,000 Sold May 30, 2025

  • 2,550 Sq Ft
  • $784/SF
  • 123 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  6940 Longboat Dr S, Longboat Key, FL 34228

  This stunning move-in-ready coastal contemporary Key West style home is located in Longboat Key's coveted historic North-end Longbeach Village area. Originally designed and custom built by Steven Carr for himself, this magnificent open-plan home offers many desirable features and finishes, including stained glass windows, vaulted wood ceilings, built-in shelving, and an elevator. Upgrades include

  Bill Anderson MICHAEL SAUNDERS & COMPANY

  6940 Longboat Dr S, Longboat Key, FL 34228
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  /59

  Est $2,522,301 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,603 Sq Ft

  240 Sands Point Rd Unit 4407, Longboat Key, FL 34228

  240 Sands Point Rd Unit 4407, Longboat Key, FL 34228
• 

  

  /79

  $8,500,000

  • 5 Beds
  • 5.5 Baths
  • 6,125 Sq Ft

  501 Harbor Point Rd, Longboat Key, FL 34228

  Rare opportunity to acquire completely remodeled waterfront residence (Finished in 2023) on Sarasota’s most prestigious barrier island of Longboat Key, in the coveted Harbors enclave of Bay Isles. Orchestrating exceptional style, comfort, and barefoot elegance, this five-bedroom home stirs the senses. Completely redesigned by renowned architect Clifford Scholz, construction was completed in

  Rich Polese COMPASS FLORIDA LLC

  501 Harbor Point Rd, Longboat Key, FL 34228
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  /100

  $25,000 per month

  • 1 Bed
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

  Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat.The expansive living room is

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
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  /2

  $1,950,000 Sold May 28, 2025

  • 2,580 Sq Ft
  • $756/SF
  • 52 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1990

  535 Sanctuary Dr Unit A202, Longboat Key, FL 34228

  Luxurious Gulf-Front Living with Breathtaking Views! Experience the pinnacle of coastal elegance in this exquisitely updated 2,580 sq. ft. condominium, offering three bedrooms and three bathrooms with stunning Gulf views from the great room, primary bedroom and terraces. Designed for modern comfort, this spacious residence features new luxury vinyl plank flooring throughout, high-end Bosch

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  535 Sanctuary Dr Unit A202, Longboat Key, FL 34228
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  /38

  Est $1,647,548 Not Listed For Sale

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

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228
• 

  

  /98

  $5,850,000

  • 5 Beds
  • 5.5 Baths
  • 3,503 Sq Ft

  7147 La Lenaire Dr, Longboat Key, FL 34228

  This is a once-in-a-lifetime opportunity to own the crown jewel of Florida's west coast. Nestled on an exclusive island, this property spans 1.35 acres and includes a private beach with endless views of aqua blue waters. When you dream of living the Florida lifestyle, this estate is truly what you envision. Accessible only by boat, this Polynesian-style waterfront sanctuary promises complete

  Jay Travis RE/MAX ALLIANCE GROUP

  7147 La Lenaire Dr, Longboat Key, FL 34228
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  /42

  $7,800 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /2

  $2,700,000 Sold May 27, 2025

  • 2,820 Sq Ft
  • $957/SF
  • 40 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1992

  415 L Ambiance Dr Unit C404, Longboat Key, FL 34228

  Nestled in the prestigious L’Ambiance community on Longboat Key’s south end, this fully furnished, turnkey residence offers 2,820 sq. ft. of refined waterfront living with breathtaking Gulf views. A double-door entry with art glass opens to a light-filled interior featuring new hurricane-resistant windows and doors, marble flooring, coral stone accents, and full-height mirrors that enhance the

  Bruce Myer COLDWELL BANKER REALTY

  415 L Ambiance Dr Unit C404, Longboat Key, FL 34228
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  /62

  Est $965,781 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  4401 Gulf of Mexico Dr Unit 706, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 706, Longboat Key, FL 34228
• 

  

  /69

  $2,800,000 New Construction

  • 3 Beds
  • 3 Baths
  • 1,971 Sq Ft

  600 de Narvaez Dr, Longboat Key, FL 34228

  The Future of Luxury Living on Longboat Key! Discover this newly constructed coastal retreat that sets the standard for modern waterfront living. Located on the private north end of Longboat Key, this turnkey-furnished residence is a sanctuary of style & elegance. Soaring 16-foot driftwood ceilings create an atmosphere of warmth and grandeur, while large impact glass sliders connect you

  Grant Sharretts COLDWELL BANKER REALTY

  600 de Narvaez Dr, Longboat Key, FL 34228
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  /21

  $45,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,961 Sq Ft
  • Condo for Rent

  2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  Step into unparalleled elegance with this stunning 4-bedroom, 4.5-bathroom beachfront condo, where modern sophistication meets coastal serenity. This exclusive residence boasts floor-to-ceiling windows that fill the space with natural light and showcase breathtaking panoramic Gulf views from every angle. Designed for ultimate privacy and comfort, the unit features direct elevator access, a

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /2

  $375,000 Sold May 27, 2025

  • 1,325 Sq Ft
  • $283/SF
  • 125 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  4500 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  DRAMATIC PRICE IMPROVEMENT! THIS IS YOUR LUCKY DAY! SELLERS ARE MOTIVATED! A blank palette to create the home that you have always dreamed of awaits. Why spend $30,000 for deconstructing and removal down to the studs of an original Windward Bay Condominium, when the work has already been completed and ready for you? Location, Location, Location! Finished remodeled condos on the same floor have

  Debby McCaig COLDWELL BANKER REALTY

  4500 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
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  /36

  Est $731,978 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 6102, Longboat Key, FL 34228

  225 Sands Point Rd Unit 6102, Longboat Key, FL 34228
• 

  

  /85

  $5,999,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,989 Sq Ft

  4651 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Experience an unparalleled coastal retreat where the gulf meets impeccable design and technology. Beyond photographs or video, stepping into this home is an invitation to a lifestyle like no other. Boasting direct oceanfront views, crafted by Hughes Design Associates, this residence epitomizes sophistication through its refined neutral palette and innovative smart home integration. Each detail

  Jo Rutstein PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4651 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
• 

  

  /35

  $8,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  3010 Grand Bay Blvd Unit 445, Longboat Key, FL 34228

  Welcome to Grand Bay on Longboat Key! Your private elevator will take you directly to your unique double-door entry. Once you are inside you are greeted with panoramic water views from all angles of your exclusive wrap-around balcony. This luxury condo is turnkey furnished with tasteful updates throughout. There are two spacious bedrooms and a third that was converted into a den with a pull-out

  Alex Roth ROSEBAY INTERNATIONAL REALTY, INC

  3010 Grand Bay Blvd Unit 445, Longboat Key, FL 34228
• 

  /2

  $2,970,000 Sold May 27, 2025

  • 1,721 Sq Ft
  • $1726/SF
  • 181 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2024

  1581 Gulf of Mexico Dr Unit 407, Longboat Key, FL 34228

  Incredible investment opportunity for the largest one-bedroom residence at The St. Regis Longboat Key. Seller will consider any and all offers. Enter from your private elevator into a dramatic living area with high ceilings and expansive glass featuring spectacular views of Sarasota Bay. The living area opens to a large outdoor terrace with a Wolf gas grill for easy entertainment. The chef’s

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1581 Gulf of Mexico Dr Unit 407, Longboat Key, FL 34228
• 

  

  /66

  Est $929,942 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

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