Longboat Key, FL Homes

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  /82

  $3,595,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft

  3540 Mistletoe Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. This spectacular direct bayfront residence is offered fully furnished and showcases a thoughtful, top-to-bottom transformation embodying refined coastal luxury. With panoramic views across Sarasota Bay and a deep-water dock equipped with a lift, this four-bedroom home is a true boater’s retreat, offering effortless access to the Bay and the Gulf of Mexico

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  3540 Mistletoe Ln, Longboat Key, FL 34228
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  /52

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228

  Seasonal / Short-Term Rental on Longboat Key /Vacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated

  Cody Smith RENT SARASOTA

  3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228
• 

  $1,425,000 Sold Nov 26, 2025

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 11 Days On Market

  Current Estimated Value $1,423,654

  Last Listing Agent Irma Scherer COMPASS FLORIDA LLC

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228
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  /48

  Est $2,103,773 Not Listed For Sale

  6957 Longboat Dr S, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,499 Sq Ft
  • Built 2019

  6957 Longboat Dr S, Longboat Key, FL 34228

  Last Sold Summary

  • 18% Below List Price
  • $1,030/SF
  • 11 Days On Market

  Last Sold Price $2,575,000

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /77

  $775,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,119 Sq Ft

  2155 Harbourside Dr Unit 804, Longboat Key, FL 34228

  Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few

  Alexis Smith-Frady COMPASS FLORIDA LLC

  2155 Harbourside Dr Unit 804, Longboat Key, FL 34228
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  /13

  $4,800 per month

  • 4 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • House for Rent

  600 Russell St, Longboat Key, FL 34228

  Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room

  Gregory Koss WAGNER REALTY

  600 Russell St, Longboat Key, FL 34228
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  /2

  $1,850,000 Sold Oct 03, 2025

  540 Gulf Bay Rd, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 1,880 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $984/SF
  • 124 Days On Market

  Current Estimated Value $1,786,234

  Last Listing Agent Brett Coady PINEYWOODS REALTY LLC

  540 Gulf Bay Rd, Longboat Key, FL 34228
• 

  

  /19

  Est $171,501 Not Listed For Sale

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228

  • Studio
  • 1,200 Sq Ft
  • Built 1987

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $167/SF
  • 281 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /89

  $4,990,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,582 Sq Ft

  4127 Gulf of Mexico Dr Unit N101, Longboat Key, FL 34228

  Under contract-accepting backup offers. Where every day unfolds like a private Gulf Coast retreat. Set directly along the shimmering waters of the Gulf of Mexico, this refined 3-bedroom, 31⁄2-bath residence at La Firenza offers an elevated expression of coastal living on Longboat Key. Encompassing approximately 3,582 square feet, the home pairs timeless elegance with a gracious, livable

  Sue Wolverton DOUGLAS ELLIMAN

  4127 Gulf of Mexico Dr Unit N101, Longboat Key, FL 34228
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  /50

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • Condo for Rent

  3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228

  BAYSIDE CONDO WITH FULL BAY VIEW AVAILABLE IMMEDIATELY FOR ANNUAL RENTAL. This lovely 2nd floor (elevator access) 2-bedroom, 2-bath Turnkey Furnished condo in a small community with heated pool, tennis court and club house is a boater's Bayside dream! The interior is nicely appointed and the kitchen opens to the dining room and living area. Full length, Spacious enclosed lanai overlooking the Bay

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228
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  /2

  $340,000 Sold Nov 25, 2025

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 747 Sq Ft
  • Built 1969

  Last Sold Summary

  • $455/SF
  • 0 Days On Market

  Current Estimated Value $338,752

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228
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  /66

  Est $3,416,933 Not Listed For Sale

  3521 Bayou Pointe, Longboat Key, FL 34228

  • 3 Beds
  • 4.5 Baths
  • 3,687 Sq Ft
  • Built 1996

  3521 Bayou Pointe, Longboat Key, FL 34228

  Last Sold Summary

  • 11% Below List Price
  • $1,044/SF
  • 35 Days On Market

  Last Sold Price $3,850,000

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
• 

  

  /79

  $8,500,000 Pending

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

  501 Harbor Point Rd, Longboat Key, FL 34228

  Under contract-accepting backup offers. 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

  Rich Polese COMPASS FLORIDA LLC

  501 Harbor Point Rd, Longboat Key, FL 34228
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  /40

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 1,350 Sq Ft
  • House for Rent

  730 Fox St, Longboat Key, FL 34228

  Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room

  Linda Votrubova ENVISION REALTY PARTNERS LLC

  730 Fox St, Longboat Key, FL 34228
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  /2

  $1,190,000 Sold Sep 05, 2025

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,721 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $691/SF
  • 51 Days On Market

  Current Estimated Value $1,153,337

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /60

  Est $1,562,886 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Built 1973

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

  Last Sold Summary

  • 2% Below List Price
  • $1,058/SF
  • 79 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY
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  /64

  $9,700,000

  • 4 Beds
  • 5 Baths
  • 5,245 Sq Ft

  560 Harbor Point Rd, Longboat Key, FL 34228

  Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost

  Jonathan Fox MICHAEL SAUNDERS & COMPANY

  560 Harbor Point Rd, Longboat Key, FL 34228
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  /20

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Condo for Rent

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and

  Christian Higgins ANDRE LECLAIR PROPERTIES LLC

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /2

  $1,750,000 Sold Oct 27, 2025

  6011 Emerald Harbor Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $907/SF
  • 0 Days On Market

  Current Estimated Value $1,724,351

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  6011 Emerald Harbor Dr, Longboat Key, FL 34228
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  /50

  Est $1,533,119 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Built 1973

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

  Last Sold Summary

  • 6% Below List Price
  • $1,112/SF
  • 0 Days On Market

  Last Sold Price $1,635,000

  Last Listing Agent Robert Delaney Michael Saunders
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  /64

  $625,000

  • 1 Bed
  • 1.5 Baths
  • 1,094 Sq Ft

  2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228

  NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228
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  /65

  $78,000 per month

  • 4 Beds
  • 4.5 Baths
  • 5,334 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

  There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the

  Inbal August DOUGLAS ELLIMAN

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
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  /2

  $1,000,000 Sold Feb 26, 2026

  3543 Mistletoe Ln, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 3,239 Sq Ft
  • Built 1991

  Last Sold Summary

  • 33% Below List Price
  • $309/SF
  • 89 Days On Market

  Current Estimated Value $1,300,968

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3543 Mistletoe Ln, Longboat Key, FL 34228
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  /36

  Est $966,821 Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft
  • Built 1982

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

  Last Sold Summary

  • 15% Below List Price
  • $1,798/SF
  • 0 Days On Market

  Last Sold Price $1,140,000

  Last Listing Agent Norma Mladineo COLDWELL BANKER REALTY
• 

  

  /79

  $3,795,000

  • 5 Beds
  • 5.5 Baths
  • 4,281 Sq Ft

  550 Yardarm Ln, Longboat Key, FL 34228

  Price improvement ....ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be

  Melanie Russell QUEST PROPERTIES INC

  550 Yardarm Ln, Longboat Key, FL 34228
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  /26

  $2,850 per month

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Condo for Rent

  554 Sutton Place, Longboat Key, FL 34228

  nnual Unfurnished Rental. Now available on beautiful Longboat Key! This spacious second-floor, two-bedroom residence combines comfort with classic coastal living, featuring a screened lanai and a large attached garage with ample storage. Wake up to stunning Bayfront sunrises and end your day with spectacular Gulf sunsets—all from your home in Sutton Place, a sought-after Gulf-to-Bay community

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  554 Sutton Place, Longboat Key, FL 34228
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  /2

  $357,000 Sold Dec 19, 2025

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 837 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $427/SF
  • 22 Days On Market

  Current Estimated Value $353,237

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228
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  /79

  Est $5,276,319 Not Listed For Sale

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

  • 5 Beds
  • 6.5 Baths
  • 5,225 Sq Ft
  • Built 1996

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

  Last Sold Summary

  • 4% Below List Price
  • $1,053/SF
  • 501 Days On Market

  Last Sold Price $5,500,000

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
• 

  

  /51

  $924,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  3235 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Under contract-accepting backup offers. * BREATHTAKING GULF-FRONT CONDO WITH PANORAMIC VIEWS AND LUXURIOUS AMENITIES! ** This stunning condo offers a unique blend of elegance and tranquility, perfectly situated to capture the serene beauty of the Gulf of Mexico. Imagine waking up to the gentle sound of waves and enjoying unobstructed views from every room. Retreat to the primary suite, a tranquil

  Shana Hamel NEXTHOME EXCELLENCE

  3235 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
• 

  

  /55

  $3,300 per month

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

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228

  Stunning Bayfront and Marina views, this is a rare opportunity for a 1 bedroom, 1 bath, FURNISHED in a 55 + community on Longboat key . This is a beautifully designed and outfitted villa in the community of Twin Shores-located Mid Key(Close to both St. Armand's Circle and Anna Maria Island). Not only are you Sitting within Steps to Panoramic Views of the Bay, you have private DEEDED beach access

  Joseph Patoray FINE PROPERTIES

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
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  /2

  $1,000,000 Sold Jul 01, 2025

  230 Sands Point Rd Unit 3501, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1982

  Last Sold Summary

  • 13% Below List Price
  • $1,333/SF
  • 58 Days On Market

  Current Estimated Value $973,086

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  230 Sands Point Rd Unit 3501, Longboat Key, FL 34228
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  /38

  Est $1,589,905 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Built 1973

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

  Last Sold Summary

  • 8% Below List Price
  • $1,173/SF
  • 23 Days On Market

  Last Sold Price $1,725,000

  Last Listing Agent Robert Delaney Michael Saunders
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  /50

  $3,299,000 Open Sat 11AM - 4PM

  • 5 Beds
  • 5 Baths
  • 3,815 Sq Ft

  2945 Pyrula Dr, Longboat Key, FL 34228

  A contemporary masterpiece awaits, constructed in 2024 and completed in 2025 this newly built residence blends contemporary architecture with uncompromising craftsmanship. Step into more than 3,800 square feet of modern design perfection ideally located in one of Longboat Keys most coveted neighborhoods. Just minutes on foot brings you to pristine beach access or a tee time at the Longboat Keys

  Alin Zdroba PROPERTIO

  2945 Pyrula Dr, Longboat Key, FL 34228
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  /69

  $40,000 per month

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228

  An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
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  /2

  $600,000 Sold Dec 08, 2025

  780 Jungle Queen Way, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 1,242 Sq Ft
  • Built 1962

  Last Sold Summary

  • 29% Below List Price
  • $483/SF
  • 207 Days On Market

  Current Estimated Value $633,879

  Last Listing Agent Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  780 Jungle Queen Way, Longboat Key, FL 34228
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  /66

  Est $923,128 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1980

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

  Last Sold Summary

  • 15% Below List Price
  • $921/SF
  • 34 Days On Market

  Last Sold Price $1,090,000

  Last Listing Agent Beth Pheney FINE PROPERTIES
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  /76

  $2,850,000 Open Thu 10AM - 12:30PM

  • 3 Beds
  • 3 Baths
  • 4,000 Sq Ft

  677 Lands End Dr, Longboat Key, FL 34228

  In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  677 Lands End Dr, Longboat Key, FL 34228
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  /28

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 721 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

  1-bed, 1-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
• 

  /2

  $2,700,000 Sold Jan 28, 2026

  6473 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,804 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Above List Price
  • $963/SF
  • 30 Days On Market

  Current Estimated Value $2,880,756

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  6473 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /47

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 657 Sq Ft
  • Built 2018

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228

  Last Sold Summary

  • $510/SF
  • 31 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Mike Sansenbach COLDWELL BANKER REALTY

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