Longboat Key, FL Homes

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  $3,895,000 Open Sun 2:30PM - 4:30PM

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

  550 Yardarm Ln, Longboat Key, FL 34228

  New Price ....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 instantly

  Melanie Russell QUEST PROPERTIES INC

  550 Yardarm Ln, Longboat Key, FL 34228
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  /24

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • Condo for Rent

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228

  Stunning Gulf-Front Condo with Breathtaking Views at Islands West! Experience the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom condominium on the 12th floor of Islands West, where full Gulf views become a part of your daily life. This beautifully furnished unit is not just a rental; it’s a lifestyle choice that offers you the chance to wake up to the soothing sounds of waves

  Jane Hunter JENNETTE PROPERTIES INC

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
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  $470,000 Sold Jan 16, 2026

  3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft
  • Built 1960

  Last Sold Summary

  • $1,130/SF
  • 9 Days On Market

  Last Listing Agent Ryndie Brusco MICHAEL SAUNDERS & COMPANY

  3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228
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  /50

  Est $1,583,150 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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  $940,000

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

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

  * 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 haven with ample closet space and an

  Shana Hamel NEXTHOME EXCELLENCE

  3235 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /59

  $14,750 per month

  • 4 Beds
  • 3.5 Baths
  • 2,292 Sq Ft
  • House for Rent

  513 Gunwale Ln, Longboat Key, FL 34228

  Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation

  Marcia Benson Berkshire Hathaway Florida Realty

  513 Gunwale Ln, Longboat Key, FL 34228
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  $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 $1,748,384

  Last Listing Agent Brett Coady PINEYWOODS REALTY LLC

  540 Gulf Bay Rd, Longboat Key, FL 34228
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  /36

  Est $979,173 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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  /99

  $1,595,000

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

  2425 Gulf of Mexico Dr Unit 10F, Longboat Key, FL 34228

  Gulf-Front Elegance | Sea Gate Club #10F | Longboat Key —Welcome to Sea Gate Club #10F, a rarely available 10th-floor end unit offering spectacular, front-row Gulf views in one of Longboat Key’s most intimate beachfront communities. Perfectly positioned mid-island along the sandy shores of the Gulf of Mexico, this elegant 2-bedroom, 2-bath residence captures direct, unobstructed views of the

  Erica Thomas MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 10F, Longboat Key, FL 34228
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  /15

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • Condo for Rent

  3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228

  Charming turnkey-furnished 2BR/2BA condo on the beautiful island of Longboat Key. Enjoy magnificent ocean views and spectacular sunsets from the private balcony. This well-appointed unit offers an ideal winter escape with comfortable living spaces and a serene coastal atmosphere. Building amenities include an in-ground heated pool, docking station, fish cleaning station, kayak/paddleboard rack,

  Juliana Brando Perez BROKER & BAKER INTERNATIONAL REALTY

  3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
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  $3,500,000 Sold Mar 14, 2025

  3460 Mistletoe Ln, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $1,207/SF
  • 80 Days On Market

  Current Estimated Value $2,988,947

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  3460 Mistletoe Ln, Longboat Key, FL 34228
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  /79

  Est $5,044,371 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
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  /59

  $1,549,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 3 Baths
  • 3,171 Sq Ft

  3210 Bayou Sound, Longboat Key, FL 34228

  Welcome to this elevated retreat in the sought-after Bayou section of Bay Isles—a seamless blend of sophisticated design and relaxed coastal elegance. Encompassing nearly 2,100 sq. ft. of sunlit interiors, this residence offers an open-concept floor plan with soaring vaulted ceilings, creating an airy, inviting ambiance ideal for both everyday living and effortless entertaining. The expansive

  Julie Lojacono Mackie COLDWELL BANKER REALTY

  3210 Bayou Sound, Longboat Key, FL 34228
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  /26

  $9,800 per month

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

  640 Broadway St, Longboat Key, FL 34228

  Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

  Christina Vescovo LPT REALTY, LLC

  640 Broadway St, Longboat Key, FL 34228
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  $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

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228
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  /59

  Est $2,342,754 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
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  /70

  $2,499,900

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft

  6322 Laguna Dr Unit 1, Longboat Key, FL 34228

  Welcome to Laguna Yacht Village on beautiful Longboat Key — a boutique waterfront gated community which includes bay access and is located across the street from the beach, offering refined coastal living at its best. This Key West–inspired, three-story single residence with an oversized 3-car garage features four bedrooms, three full baths, and over 2,886 square feet of beautifully designed

  Brandy Coffey KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  6322 Laguna Dr Unit 1, Longboat Key, FL 34228
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  $14,400 per month

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances

  Christina Vescovo LPT REALTY, LLC

  701 Broadway St, Longboat Key, FL 34228
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  $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 $1,145,068

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  Est $1,583,404 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
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  /30

  $3,350,000 Open Sat 11AM - 5PM

  • 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 prestigious

  Alin Zdroba PROPERTIO

  2945 Pyrula Dr, Longboat Key, FL 34228
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  /23

  $5,000 per month

  • 1 Bed
  • 1.5 Baths
  • 725 Sq Ft
  • Condo for Rent

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

  Desirable Furnished One Bedroom 1 1/2 Bathroom Condo on Longboat Key. It is on the 7th floor with a 20 ft lanai that has an outstanding view of the beach and the Gulf of America. The building is one of the closest to the beach with access within few feet of the building, is well managed, has a salt water heated pool & recreational area with gas grill. There is an exercise center, public kitchen,

  David Gardner PINEBROOK IRONWOOD REALTY

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
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  $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 $1,744,786

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  6011 Emerald Harbor Dr, Longboat Key, FL 34228
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  /66

  Est $881,261 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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  /42

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft

  615 Dream Island Place Unit 105, Longboat Key, FL 34228

  Price Drop, priced to sell. Welcome to Paradise Found at Harbour Villa Club, a waterfront luxury condo that is truly a slice of heaven on earth. This stunning property offers breathtaking views of the glistening water and is situated in a prime location that is peaceful, serene, and truly one-of-a-kind. A true Longboat Key gem. As you step inside this luxurious fully renovated (2025) condo,

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  615 Dream Island Place Unit 105, Longboat Key, FL 34228
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  /35

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228

  2-bed, 2-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 211, Longboat Key, FL 34228
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  $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

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 657 Sq Ft

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

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228
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  $1,395,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property

  Rinat Sikdar COLDWELL BANKER REALTY

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /40

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • House for Rent

  573 Spanish Dr N, Longboat Key, FL 34228

  NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL ($4,600/MONTH). LEASE -3 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

  Norma Mladineo COLDWELL BANKER REALTY

  573 Spanish Dr N, Longboat Key, FL 34228
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  $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 $985,518

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  230 Sands Point Rd Unit 3501, Longboat Key, FL 34228
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  Est $763,438 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /48

  $1,450,000

  • 2 Beds
  • 2 Baths
  • 1,491 Sq Ft

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228

  Ultra-luxury, fully remodeled Gulf-front residence on Longboat Key. This sixth-floor, move-in ready condo at Islands West comes furnished and showcases imported Italian cabinetry, level 5 drywall, carrara marble flooring, aqua quartz countertops and steam shower. All-new hurricane-impact windows and doors, including floor-to-ceiling glass in both bedrooms, frame sweeping water views and a

  Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228
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  $25,000 per month

  • 1 Bed
  • 1.5 Baths
  • 1,721 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  $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

  Last Listing Agent Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  780 Jungle Queen Way, Longboat Key, FL 34228
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  /28

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 720 Sq Ft

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228
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  $1,045,000

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228

  Bring your boat to Longboat Key. Fully furnished second floor corner unit with boat dock and stunning views of the Sarasota Bay in beautiful Harbor Villa Club. This beautifully renovated 2-bedroom, 2-bathroom condo is an incredible opportunity to live right on the Sarasota bay with 180 degree breathtaking water views. This single level, corner unit has plenty of natural light and has been updated

  Greg Orquera ORQUERA FLORIDA INVESTMENTS

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228
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  /31

  $10,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  $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

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  6473 Gulf of Mexico Dr, Longboat Key, FL 34228
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  Est $646,312 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

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