Longboat Key, FL Homes

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  $2,499,500

  • 3 Beds
  • 3 Baths
  • 3,768 Sq Ft

  3421 Bayou Sound, Longboat Key, FL 34228

  Stunning Bay Isles Estate HomeLocated within the prestigious double gated estate section of Bay Isles, this elegantly appointed residence offers exceptional privacy, refined finishes, and direct canal frontage with a private boat dock. The home features a spacious open floor plan with vaulted ceilings, abundant natural light, and seamless indoor outdoor living designed for both comfort and

  Stephen Strong MICHAEL SAUNDERS & COMPANY

  3421 Bayou Sound, Longboat Key, FL 34228
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  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Condo for Rent

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228

  Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so

  Armando Gonzalez AG REALTY SERVICES LLC

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228
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  $8,625,000 Sold Feb 23, 2026

  600 Wedge Ln, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 4,338 Sq Ft
  • Built 2016

  Last Sold Summary

  • 13% Below List Price
  • $1,988/SF
  • 65 Days On Market

  Current Estimated Value $9,554,128

  Last Listing Agent Debra Lichter SARASOTA BEACH TO BAY INC

  600 Wedge Ln, Longboat Key, FL 34228
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  Est $272,608 Not Listed For Sale

  2600 Harbourside Dr Unit Q5, Longboat Key, FL 34228

  • Studio
  • Built 1983

  2600 Harbourside Dr Unit Q5, Longboat Key, FL 34228

  Last Sold Summary

  • 9% Below List Price
  • 59 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Mark J Baron COLDWELL BANKER REALTY
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  $2,250,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 2,848 Sq Ft

  6810 Longboat Dr S, Longboat Key, FL 34228

  Significant Price Reduction on this NEW in 2024, dream retreat that is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  6810 Longboat Dr S, Longboat Key, FL 34228
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  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Condo for Rent

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

  ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
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  $525,000 Sold Mar 13, 2026

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $490/SF
  • 87 Days On Market

  Current Estimated Value $615,895

  Last Listing Agent Marsha Winegarden WAGNER REALTY

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228
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  Est $1,577,576 Not Listed For Sale

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1981

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $1,131/SF
  • 8 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  /83

  $2,495,000

  • 4 Beds
  • 4.5 Baths
  • 2,900 Sq Ft

  333 Firehouse Ct, Longboat Key, FL 34228

  Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900

  Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  333 Firehouse Ct, Longboat Key, FL 34228
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  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • House for Rent

  957 Spanish Dr N, Longboat Key, FL 34228

  AVAILABLE STARTING MAY 1, 2026. WITH 4 MONTH MINUMUM RENTAL DURING SEASON and 3 MONTHS OFF SEASON. FULL WATERFRONT NEWLY RENOVATED and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main

  Norma Mladineo COLDWELL BANKER REALTY

  957 Spanish Dr N, Longboat Key, FL 34228
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  $2,900,000 Sold May 22, 2025

  3580 Fair Oaks Ln, Longboat Key, FL 34228

  • 5 Beds
  • 5.5 Baths
  • 4,167 Sq Ft
  • Built 1998

  Last Sold Summary

  • 17% Below List Price
  • $696/SF
  • 75 Days On Market

  Current Estimated Value $2,777,904

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  3580 Fair Oaks Ln, Longboat Key, FL 34228
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  Not Listed For Sale

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Built 1970

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  Last Sold Summary

  • $1,134/SF
  • 132 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Mark Midyett KELLER WILLIAMS ON THE WATER S
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  /85

  $1,050,000

  • 2 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  3435 Winding Oaks Dr Unit 18, Longboat Key, FL 34228

  Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders

  Sean Clark MICHAEL SAUNDERS & COMPANY

  3435 Winding Oaks Dr Unit 18, Longboat Key, FL 34228
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  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Condo for Rent

  534 Sutton Place, Longboat Key, FL 34228

  Available for annual lease starting 5/1/2026! GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience Island living on Longboat Key. This 2 bedroom, 2 bathroom condo has a spacious living and dining room combo, which opens to a bright and airy Florida room, perfect for relaxing or entertaining. The Florida room is fully enclosed,

  Tanner Frey KELLER WILLIAMS ON THE WATER S

  534 Sutton Place, Longboat Key, FL 34228
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  $625,000 Sold Aug 07, 2025

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228

  • Land
  • 0.14 Acre
  • $4,464,286 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 185 Days On Market

  Current Estimated Value $614,567

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228
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  /31

  Est $848,739 Not Listed For Sale

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

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

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $1,502/SF
  • 4 Days On Market

  Last Sold Price $987,000

  Last Listing Agent Ian Addy, PA Michael Saunders
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  $775,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  803 Bayport Way Unit 803, Longboat Key, FL 34228

  Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit

  Alexis Smith-Frady COMPASS FLORIDA LLC

  803 Bayport Way Unit 803, Longboat Key, FL 34228
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  /25

  $11,000 per month

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Condo for Rent

  1000 Longboat Club Rd, Longboat Key, FL 34228

  Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd, Longboat Key, FL 34228
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  $580,000 Sold Jun 25, 2025

  681 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $716/SF
  • 4 Days On Market

  Current Estimated Value $580,090

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  681 Fox St, Longboat Key, FL 34228
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  /53

  Est $725,243 Not Listed For Sale

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft
  • Built 1983

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • $1,322/SF
  • 34 Days On Market

  Last Sold Price $849,000

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /19

  $375,000

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228

  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

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
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  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228

  Available for season 2026! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by

  Maureen Plichta STRINGER MANAGEMENT INC

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
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  $6,000,000 Sold Oct 03, 2025

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $1,917/SF
  • 99 Days On Market

  Current Estimated Value $5,959,653

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228
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  /31

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 621 Sq Ft
  • Built 1961

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  Last Sold Summary

  • $403/SF
  • 28 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $649,900

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

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228

  Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit!Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms,

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228
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  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • House for Rent

  6979 Longboat Dr S, Longboat Key, FL 34228

  Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room

  Rinat Sikdar COLDWELL BANKER REALTY

  6979 Longboat Dr S, Longboat Key, FL 34228
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  $3,350,000 Sold Nov 21, 2025

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 3,060 Sq Ft
  • Built 1997

  Last Sold Summary

  • 21% Below List Price
  • $1,095/SF
  • 92 Days On Market

  Current Estimated Value $3,397,319

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228
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  Est $419,090 Not Listed For Sale

  4770 Gulf of Mexico Dr Unit Villa 6, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1974

  4770 Gulf of Mexico Dr Unit Villa 6, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $493/SF
  • 0 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Debby McCaig COLDWELL BANKER REALTY
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  /28

  $595,000

  • Land
  • 0.14 Acre
  • $4,250,000 per Acre

  641 Broadway St, Longboat Key, FL 34228

  Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available on Longboat Key, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities,

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  641 Broadway St, Longboat Key, FL 34228
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  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

  Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
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  $535,000 Sold Apr 22, 2025

  660 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 1968

  Last Sold Summary

  • 11% Below List Price
  • $434/SF
  • 24 Days On Market

  Current Estimated Value $527,519

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  660 Fox St, Longboat Key, FL 34228
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  Est $484,817 Not Listed For Sale

  3320 Gulf of Mexico Dr Unit 302C, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1971

  3320 Gulf of Mexico Dr Unit 302C, Longboat Key, FL 34228

  Last Sold Summary

  • 1% Above List Price
  • $403/SF
  • 48 Days On Market

  Last Sold Price $478,000

  Last Listing Agent Karin Leereveld COLDWELL BANKER REALTY
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  /46

  $500,000 Pending

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

  6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228

  In the sought-after Whitney Beach community on Longboat Key’s peaceful north end, this beautifully renovated two-bedroom, two-bath end unit residence offers 1,449 square feet of coastal contemporary living with tranquil water views over protected Bishop’s Bayou. Enjoy serenity of a coastal inlet sheltered from constant boat traffic of the Intracoastal Waterway, where dolphins and manatees glide

  Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
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  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Townhouse for Rent

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip

  Victoria Campbell LPT REALTY LLC

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
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  $629,950 Sold Mar 24, 2026

  3070 Grand Bay Blvd Unit 612, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,371 Sq Ft
  • Built 1995

  Last Sold Summary

  • 9% Below List Price
  • $459/SF
  • 103 Days On Market

  Current Estimated Value $648,910

  Last Listing Agent Andree Huffine COLDWELL BANKER REALTY

  3070 Grand Bay Blvd Unit 612, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1977

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228

  Last Sold Summary

  • $260/SF
  • 65 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $2,400,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228

  Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2025, fee for

  Michael Moulton MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228
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  $17,500 per month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  613 Buttonwood Dr, Longboat Key, FL 34228

  Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into

  Jennifer LeBlanc PRECISE REALTY CORP

  613 Buttonwood Dr, Longboat Key, FL 34228
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  $1,205,000 Sold Apr 07, 2025

  3060 Grand Bay Blvd Unit 162, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,143 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $562/SF
  • 70 Days On Market

  Current Estimated Value $1,219,795

  Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3060 Grand Bay Blvd Unit 162, Longboat Key, FL 34228
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  Not Listed For Sale

  90 Main Street Dr, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 568 Sq Ft
  • Built 1959

  90 Main Street Dr, Longboat Key, FL 34228

  Last Sold Summary

  • $185/SF
  • 21 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Crystal Cain RE/MAX

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