Longboat Key, FL Homes

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  /46

  $359,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,427 Sq Ft

  602 Spanish Dr S Unit 115, Longboat Key, FL 34228

  Virtually Staged. Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave

  

  Toni Zarghami

  KW COASTAL LIVING III

  602 Spanish Dr S Unit 115, Longboat Key, FL 34228
• Explore Longboat Key

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  /34

  $7,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Condo for Rent

  737 Bayport Way Unit D, Longboat Key, FL 34228

  BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two

  

  Marianne LeBar

  CENTURY 21 ROSEBAY

  737 Bayport Way Unit D, Longboat Key, FL 34228
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  /2

  $655,000

  Sold Dec 10, 2025

  560 Cedar St, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft
  • Built 1970

  Last Sold Summary

  • 12% Below List Price
  • $359/SF
  • 64 Days On Market

  Current Estimated Value $978,358

  Last Listing Agent Lauren Hofing THE KEYES COMPANY - SARASOTA

  560 Cedar St, Longboat Key, FL 34228
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  /2

  Est $615,938

  Not Listed For Sale

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

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

  Last Sold Summary

  • 185 Days On Market

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY
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  /82

  $949,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  806 Bayport Way Unit 806, Longboat Key, FL 34228

  Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a sereneenvironment.Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  806 Bayport Way Unit 806, Longboat Key, FL 34228
• 

  

  /20

  $11,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Condo for Rent

  807 Bayport Way, Longboat Key, FL 34228

  Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM

  807 Bayport Way, Longboat Key, FL 34228
• 

  /2

  $4,750,000

  Sold May 06, 2026

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

  • 3 Beds
  • 3.5 Baths
  • 3,582 Sq Ft
  • Built 2007

  Last Sold Summary

  • 5% Below List Price
  • $1,326/SF
  • 58 Days On Market

  Current Estimated Value $4,628,066

  Last Listing Agent Sue Wolverton DOUGLAS ELLIMAN

  4127 Gulf of Mexico Dr Unit N101, Longboat Key, FL 34228
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  /2

  Est $465,897

  Not Listed For Sale

  7030 Lois Ave, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1948

  7030 Lois Ave, Longboat Key, FL 34228

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES
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  /67

  $2,350,000

  • 3 Beds
  • 3 Baths
  • 2,485 Sq Ft

  2165 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  2165 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  /30

  $7,750 Per Month

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
• 

  /2

  $475,000

  Sold Jun 26, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft
  • Built 1970

  Last Sold Summary

  • 5% Below List Price
  • $328/SF
  • 94 Days On Market

  Current Estimated Value $486,444

  Last Listing Agent Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
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  /2

  Est $3,133,105

  Not Listed For Sale

  689 Lands End Dr, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 3,254 Sq Ft
  • Built 2005

  689 Lands End Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 140 Days On Market

  Last Listing Agent Matthew Voss PREFERRED SHORE LLC
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  /64

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,827 Sq Ft

  3301 Bayou Rd, Longboat Key, FL 34228

  Located within the gated and highly desirable community of Bay Isles on Longboat Key, this 4 bedroom, 3 bathroom pool home encompasses 2827 square feet of living space. The residence features a functional and spacious floor plan, including a well-appointed bedroom layout, an open kitchen and family room combo, and a formal living and dining room combo. This property is priced competitively,

  

  Michele Tanner

  PREFERRED SHORE LLC

  3301 Bayou Rd, Longboat Key, FL 34228
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  /20

  $19,798

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft
  • Condo for Rent

  4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228

  The advertised rate of $19,799/month is the lowest available price, based on a 1 month(s) and 1 day(s) stay with a move-in date of February 4, 2028.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

  4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
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  /2

  $549,000

  Sold Feb 05, 2026

  2045 Gulf of Mexico Dr Unit M1410, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Built 1974

  Last Sold Summary

  • $592/SF
  • 0 Days On Market

  Current Estimated Value $569,596

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  2045 Gulf of Mexico Dr Unit M1410, Longboat Key, FL 34228
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  /2

  Est $518,401

  Not Listed For Sale

  2045 Gulf of Mexico Dr Unit M1514, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Built 1974

  2045 Gulf of Mexico Dr Unit M1514, Longboat Key, FL 34228

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES
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  /93

  $4,550,000

  Open House 8/23 $450K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,209 Sq Ft

  1571 Harbor Cay Ln, Longboat Key, FL 34228

  Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key.Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area

  

  Julie Klick

  MICHAEL SAUNDERS & COMPANY

  1571 Harbor Cay Ln, Longboat Key, FL 34228
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  /52

  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  833 Bayport Way Unit 833, Longboat Key, FL 34228

  WELCOMING and tastefully decorated, this fully furnished 2 bedroom, 2 bathroom unit offers a relaxing atmosphere. The open concept floor plan with split bedrooms is spacious and inviting and this unit features two interior patios with serene canopy garden views. This amenity-rich community at sea’s edge is situated in the middle of Longboat Key and features 27 picturesque acres of well maintained

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  833 Bayport Way Unit 833, Longboat Key, FL 34228
• 

  /2

  $3,300,000

  Sold Aug 14, 2025

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 4 Beds
  • 4 Baths
  • 2,943 Sq Ft
  • Built 1959

  Last Sold Summary

  • 27% Below List Price
  • $1,121/SF
  • 154 Days On Market

  Current Estimated Value $3,479,403

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /2

  Est $314,552

  Not Listed For Sale

  3806 Gulf of Mexico Dr Unit C205, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Built 1970

  3806 Gulf of Mexico Dr Unit C205, Longboat Key, FL 34228

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Kay Winefordner DALTON WADE INC
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  /61

  $885,000

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

  7115 Gulf of Mexico Dr Unit 23, Longboat Key, FL 34228

  Never miss another beach day or a green flash sunset in this rarely available 2 bed 2 bath home in the Longbeach Community- a GULF FRONT enclave on the tip of Longboat Key. A short walk to the beach, thoughtfully remodeled and move-in ready, this residence offers spectacular daily views of the Gulf, pool, and lush tropical landscaping- best enjoyed on the 200 sqft screened terrace where there’s

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  7115 Gulf of Mexico Dr Unit 23, Longboat Key, FL 34228
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  /20

  $6,189

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,388 Sq Ft
  • Condo for Rent

  1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228

  The advertised rate of $6,190/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
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  /2

  $724,000

  Sold Jul 20, 2026

  2020 Harbourside Dr Unit 457, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1984

  Last Sold Summary

  • $502/SF
  • 2 Days On Market

  Current Estimated Value $750,984

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2020 Harbourside Dr Unit 457, Longboat Key, FL 34228
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  /57

  Est $3,933,478

  Not Listed For Sale

  6941 Bayside Dr, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 2023

  6941 Bayside Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent Kate Enis FINE PROPERTIES
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  /57

  $3,200,000

  $300K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  435 L Ambiance Dr Unit L807, Longboat Key, FL 34228

  Sunrise to Sunset Views - Your Coastal Paradise awaits you at L'Ambiance!** 2 bedrooms with an open den --step into a world of instant enjoyment. Nestled along the stunning Gulf of Mexico, L'Ambiance offers you a front-row seat to Sarasota's dramatic sunrises and captivating sunsets. This exceptional corner residence is a rare gem, designed to help you create a lifetime of cherished memories. As

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  435 L Ambiance Dr Unit L807, Longboat Key, FL 34228
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  /58

  $9,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228

  Introducing a remarkable opportunity to rent a piece of paradise at 829 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. As you enter the community, you are greeted by meticulously landscaped grounds that set the

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228
• 

  /2

  $1,600,625

  Sold Jul 28, 2026

  2425 Gulf of Mexico Dr Unit 14E, Longboat Key, FL 34228

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

  Last Sold Summary

  • 6% Below List Price
  • $1,089/SF
  • 98 Days On Market

  Current Estimated Value $1,653,880

  Last Listing Agent Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 14E, Longboat Key, FL 34228
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  /30

  Est $521,512

  Not Listed For Sale

  225 Sands Point Rd Unit 6105, Longboat Key, FL 34228

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

  225 Sands Point Rd Unit 6105, Longboat Key, FL 34228

  Last Sold Summary

  • 199 Days On Market

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
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  /35

  $4,300,000

  • 4 Beds
  • 5 Baths
  • 4,364 Sq Ft

  657 Halyard Ln, Longboat Key, FL 34228

  Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  657 Halyard Ln, Longboat Key, FL 34228
• 

  

  /20

  $6,345

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft
  • Condo for Rent

  320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228

  The advertised rate of $6,345/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
• 

  /2

  $1,500,000

  Sold Aug 19, 2025

  1701 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $967/SF
  • 81 Days On Market

  Current Estimated Value $1,508,826

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  1701 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228
• 

  

  /25

  Est $964,968

  Not Listed For Sale

  230 Sands Point Rd Unit 3503, Longboat Key, FL 34228

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

  230 Sands Point Rd Unit 3503, Longboat Key, FL 34228

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Richard Perlman MICHAEL SAUNDERS & COMPANY
• 

  

  /96

  $3,499,900

  Open House 8/23

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft

  562 Ranger Ln, Longboat Key, FL 34228

  Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern

  

  Cheri Castro

  MICHAEL SAUNDERS & COMPANY

  562 Ranger Ln, Longboat Key, FL 34228
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  /44

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228

  Experience true beachfront living at 5611 Gulf of Mexico Drive, Unit 3103. This beautifully kept 3-bedroom, 2-bath residence is in excellent condition and offers stunning views of the Gulf of Mexico in a setting that is hard to beat. Located directly on the beach with no road to cross, this property gives you effortless access to the shoreline just steps from your door. Guests can enjoy the

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
• 

  /2

  $675,000

  Sold May 15, 2026

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1970

  Last Sold Summary

  • 21% Below List Price
  • $485/SF
  • 80 Days On Market

  Current Estimated Value $675,828

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  /56

  Est $941,577

  Not Listed For Sale

  4311 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,239 Sq Ft
  • Built 1977

  4311 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Tiffany Nisbet RE/MAX ALLIANCE GROUP
• 

  

  /49

  $1,800,000

  Open House 8/23 $200K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,383 Sq Ft

  2450 Harbourside Dr Unit 234, Longboat Key, FL 34228

  Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized

  

  Beverly St Hilaire

  MICHAEL SAUNDERS & COMPANY

  2450 Harbourside Dr Unit 234, Longboat Key, FL 34228
• 

  

  /20

  $5,886

  Total Monthly Price

  • 1 Bed
  • 2 Baths
  • 1,076 Sq Ft
  • Condo for Rent

  6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228

  The advertised rate of $5,886/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 12, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
• 

  /2

  $1,075,000

  Sold Oct 16, 2025

  240 Sands Point Rd Unit 4403, Longboat Key, FL 34228

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

  Last Sold Summary

  • 1% Below List Price
  • $1,717/SF
  • 2 Days On Market

  Current Estimated Value $1,078,207

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  240 Sands Point Rd Unit 4403, Longboat Key, FL 34228
• 

  /2

  Not Listed For Sale

  74 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1974

  74 Twin Shores Blvd, Longboat Key, FL 34228

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

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