Longboat Key, FL Homes

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  /27

  $525,000

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228

  Enjoy relaxed coastal living in this turnkey furnished 1 bedroom, 1 bath residence located in the Gulf front community of Silver Sands Gulf Beach Resort. This first floor unit features an open living and dining layout that extends to a private screened lanai overlooking the communities tropical landscaping. Recent improvements include a new A/C system, new kitchen appliances, and a new hot water

  Stephen Strong MICHAEL SAUNDERS & COMPANY

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228
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  /37

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,602 Sq Ft
  • Condo for Rent

  775 Longboat Club Rd Unit 405, Longboat Key, FL 34228

  AVAILABLE 2026 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness

  Brenda Cozy COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
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  $1,000,000 Sold Apr 25, 2025

  3360 Bayou, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1981

  Last Sold Summary

  • 23% Below List Price
  • $520/SF
  • 5 Days On Market

  Last Listing Agent Stephen Strong MICHAEL SAUNDERS & COMPANY

  3360 Bayou, Longboat Key, FL 34228
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  /91

  Est $1,961,495 Not Listed For Sale

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,485 Sq Ft
  • Built 1996

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $845/SF
  • 127 Days On Market

  Last Sold Price $2,100,000

  Last Listing Agent Candy Swick CANDY SWICK & COMPANY
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  /77

  $629,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true

  John Esser KELLER WILLIAMS ON THE WATER S

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /51

  $11,000 per month

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Condo for Rent

  1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

  Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The

  Margaret Young JENNETTE PROPERTIES, INC.

  1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
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  /2

  $640,000 Sold Oct 07, 2025

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

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

  Last Sold Summary

  • 8% Below List Price
  • $459/SF
  • 11 Days On Market

  Current Estimated Value $831,767

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /53

  Est $840,365 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1963

  Unlisted Address

  Last Sold Summary

  • 5% Below List Price
  • $495/SF
  • 136 Days On Market

  Last Sold Price $881,000

  Last Listing Agent Bill Anderson Michael Saunders
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  /30

  $370,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  620 Spanish Dr N, Longboat Key, FL 34228

  Some Photo's have been virtually staged. Don't miss this rare opportunity to own a renovated standalone villa with a lake view on Longboat Key! This very light, bright, and charming 2 bedroom 2 bath home is almost ready for occupancy at an exceptionally low price. As you enter the home, you can see a lovely lake view through the large back windows. The rear, shady, landscaped patio is a perfect

  Adrienne Scott MICHAEL SAUNDERS & COMPANY

  620 Spanish Dr N, Longboat Key, FL 34228
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  /22

  $7,000 per month

  • 1 Bed
  • 2 Baths
  • 1,244 Sq Ft
  • Condo for Rent

  655 Cedars Ct, Longboat Key, FL 34228

  AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay

  Brenda Cozy COLDWELL BANKER REALTY

  655 Cedars Ct, Longboat Key, FL 34228
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  /2

  $3,170,000 Sold Aug 08, 2025

  689 Lands End Dr, Longboat Key, FL 34228

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

  Last Sold Summary

  • 17% Below List Price
  • $974/SF
  • 140 Days On Market

  Current Estimated Value $3,216,026

  Last Listing Agent Matthew Voss PREFERRED SHORE LLC

  689 Lands End Dr, Longboat Key, FL 34228
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  /63

  Est $1,398,210 Not Listed For Sale

  621 Buttonwood Dr, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,530 Sq Ft
  • Built 1967

  621 Buttonwood Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $642/SF
  • 27 Days On Market

  Last Sold Price $1,625,000

  Last Listing Agent Andrew Reese COLDWELL BANKER SUNSTAR REALTY
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  /67

  $750,000

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  490 N Shore Rd Unit 6, Longboat Key, FL 34228

  This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  490 N Shore Rd Unit 6, Longboat Key, FL 34228
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  /53

  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,349 Sq Ft
  • House for Rent

  501 Channel Ln, Longboat Key, FL 34228

  Looking for a 3 month renter for January, February, and March or the month of January 2026. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy

  Jennifer LeBlanc PRECISE REALTY CORP

  501 Channel Ln, Longboat Key, FL 34228
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  /2

  $1,575,000 Sold Jun 11, 2025

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,180 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $722/SF
  • 124 Days On Market

  Current Estimated Value $1,541,412

  Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228
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  /61

  Est $1,221,820 Not Listed For Sale

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft
  • Built 1974

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  Last Sold Summary

  • 9% Below List Price
  • $922/SF
  • 1 Day On Market

  Last Sold Price $1,350,000

  Last Listing Agent Sherri Mills Michael Saunders
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  /67

  $4,995,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  681 Old Compass Rd, Longboat Key, FL 34228

  Welcome to a crisp & clean Florida ranch. Located in popular Emerald Harbor which is a bayside enclave of just 82 homes. Homes are located on broad lagoon-style canals that provide direct boating access to Sarasota Bay. 20 ft. private Beach access is a real bonus for sunworshippers. This 3 bedroom 3.5 bath custom home blends Dutch Cape and West Indies architectural style. It is a split design

  Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  681 Old Compass Rd, Longboat Key, FL 34228
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  /34

  $7,200 per month

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

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
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  /2

  $740,000 Sold Jan 15, 2026

  2120 Harbourside Dr Unit 617, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,039 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $363/SF
  • 44 Days On Market

  Current Estimated Value $757,620

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2120 Harbourside Dr Unit 617, Longboat Key, FL 34228
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  /45

  Est $1,041,224 Not Listed For Sale

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft
  • Built 1972

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228

  Last Sold Summary

  • 23% Below List Price
  • $1,027/SF
  • 8 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Thomas Washburn BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE
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  /54

  $4,950,000 Pending

  • 4 Beds
  • 6 Baths
  • 4,145 Sq Ft

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228

  Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers

  Toni Zarghami KW COASTAL LIVING III

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /28

  $6,000 per month

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

  5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

  Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
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  /2

  $1,538,000 Sold Oct 08, 2025

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,180 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $706/SF
  • 46 Days On Market

  Current Estimated Value $1,545,546

  Last Listing Agent Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /28

  Est $2,888,290 Not Listed For Sale

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft
  • Built 1996

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $1,018/SF
  • 54 Days On Market

  Last Sold Price $3,100,000

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
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  /5

  $35,000

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228

  Welcome to Slip #2112 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6''Lx8'6''Wx7'2''H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228
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  /28

  $10,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft
  • Condo for Rent

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228

  Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the

  Deserea Hardy ROSSI & COMPANY INC

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
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  $3,000,000 Sold Mar 04, 2026

  601 Triton Bend, Longboat Key, FL 34228

  • 4 Beds
  • 5 Baths
  • 3,313 Sq Ft
  • Built 2017

  Last Sold Summary

  • 13% Below List Price
  • $906/SF
  • 160 Days On Market

  Current Estimated Value $3,187,386

  Last Listing Agent Gina Ursini BRISTA REALTY LLC

  601 Triton Bend, Longboat Key, FL 34228
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  /67

  Est $1,426,024 Not Listed For Sale

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft
  • Built 1999

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Above List Price
  • $496/SF
  • 37 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Jennifer Linehan Michael Saunders
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  /45

  $999,500

  • 3 Beds
  • 2.5 Baths
  • 2,219 Sq Ft

  2367 Harbour Oaks Dr, Longboat Key, FL 34228

  Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42

  Sandra Endres COLDWELL BANKER REALTY

  2367 Harbour Oaks Dr, Longboat Key, FL 34228
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  /66

  $7,200 per month

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

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous

  C. Alison Hunter JENNETTE PROPERTIES INC

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  $82,400 Sold Dec 19, 2025

  96 Main Street Dr, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft
  • Built 1973

  Last Sold Summary

  • 28% Below List Price
  • $129/SF
  • 233 Days On Market

  Last Listing Agent Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  96 Main Street Dr, Longboat Key, FL 34228
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  /31

  Est $733,927 Not Listed For Sale

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 955 Sq Ft
  • Built 1972

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $890/SF
  • 41 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Jerry Barnes REALTY SERVICES INC
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  /5

  $68,500

  408 Gulf of Mexico Dr Unit 2224, Longboat Key, FL 34228

  Welcome to Slip #2224 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront locations. This premium slip accommodates boats up to 30 feet in length, with a maximum height of 7' 8" and a 8.6 ft beam (No T-tops unless collapsible). Enjoy first-class

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 2224, Longboat Key, FL 34228
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  /25

  $11,000 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228

  SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
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  $950,000 Sold Jul 15, 2025

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

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

  Last Sold Summary

  • 7% Below List Price
  • $769/SF
  • 60 Days On Market

  Current Estimated Value $978,186

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228
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  /35

  Est $950,282 Not Listed For Sale

  1085 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1981

  1085 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Last Sold Summary

  • 4% Below List Price
  • $547/SF
  • 224 Days On Market

  Last Sold Price $995,000

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /10

  $1,000,000

  • Land
  • 0.45 Acre
  • $2,222,222 per Acre

  6608 Gulf of Mexico Dr, Longboat Key, FL 34228

  Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond two estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6608 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /22

  $5,500 per month

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

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and sliding glass doors, new laminate flooring

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /2

  $1,050,000 Sold Jul 21, 2025

  650 Penfield St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 1978

  Last Sold Summary

  • 19% Below List Price
  • $665/SF
  • 127 Days On Market

  Current Estimated Value $1,003,622

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  650 Penfield St, Longboat Key, FL 34228
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  /45

  Est $1,115,949 Not Listed For Sale

  3115 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1974

  3115 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  Last Sold Summary

  • 12% Above List Price
  • $867/SF
  • 14 Days On Market

  Last Sold Price $1,000,000

  Last Listing Agent Sherri Mills Michael Saunders

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