Longboat Key, FL Homes

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  $1,495,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  691 Gulf Bay Rd, Longboat Key, FL 34228

  Tucked away on one of Longboat Key’s most unexpectedly serene streets, this elevated 3-bedroom island home offers something increasingly rare: space, privacy, nature, and convenient coastal living, all in one place. Set on an expansive 18,000-square-foot double lot, the home is located at the end of a quiet dead-end road that gently meets Sarasota Bay, with deeded access to both the beach and the

  Angela Scott MICHAEL SAUNDERS & COMPANY

  691 Gulf Bay Rd, Longboat Key, FL 34228
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  $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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  $1,575,000 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 $1,469,139

  Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228
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  /31

  Est $730,717 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 955 Sq Ft

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

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

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2120 Harbourside Dr Unit 617, Longboat Key, FL 34228
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  Est $1,005,679 Not Listed For Sale

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

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

  1085 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  $695,000 Open Sat 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  4350 Chatham Dr Unit 208, Longboat Key, FL 34228

  PRICE IMPROVEMENT. REDUCED $54,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCELongboat Harbour • Unit 208 | Corner End Unit • Bay & Harbour Views.Welcome to an exquisite, newly remodeled second-floor corner residence in the highly sought-after Longboat Harbour community. Reimagined with sophisticated coastal design, this light-filled home captures sweeping views of Sarasota Bay and

  Billie Chipain COLDWELL BANKER REALTY

  4350 Chatham Dr Unit 208, Longboat Key, FL 34228
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  $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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  $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 $1,529,175

  Last Listing Agent Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  Est $1,028,912 Not Listed For Sale

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

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

  3115 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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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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  $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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  $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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  Est $412,722 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft

  3802 Gulf of Mexico Dr Unit A203, Longboat Key, FL 34228

  3802 Gulf of Mexico Dr Unit A203, Longboat Key, FL 34228
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  $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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  $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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  $580,000 Sold Feb 28, 2025

  4330 Falmouth Dr Unit 308, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,342 Sq Ft
  • Built 1969

  Last Sold Summary

  • 3% Below List Price
  • $432/SF
  • 39 Days On Market

  Current Estimated Value $557,157

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4330 Falmouth Dr Unit 308, Longboat Key, FL 34228
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  Est $2,679,390 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,054 Sq Ft

  1281 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  1281 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /19

  $5,299,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,826 Sq Ft

  2944 Gulf of Mexico Dr, Longboat Key, FL 34228

  Under Construction. Poised along one of Longboat Key’s most coveted stretches, this new semi-custom estate by Mason Martin Builders delivers sophisticated coastal living with rare peace of mind. Each level is designed to capture sweeping Gulf views without the exposure of direct beachfront placement, creating a residence that feels both refined and protected. It is your private sanctuary by the

  Kaisen Mitchell COLDWELL BANKER REALTY

  2944 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $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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  $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 $918,529

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228
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  Est $1,409,879 Not Listed For Sale

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

  1055 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  1055 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
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  $13,000,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 4,187 Sq Ft

  1561 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

  Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the

  Michael Moulton MICHAEL SAUNDERS & COMPANY

  1561 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
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  $8,000 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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  $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 $1,005,281

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  650 Penfield St, Longboat Key, FL 34228
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  /31

  Est $969,104 Not Listed For Sale

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

  1095 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  1095 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  $1,450,000 Pending

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

  2425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228

  Under contract-accepting backup offers. Newly remodeled Beachfront walkout unit, just steps to the sand. You can live front row to the Gulf and beautiful Longboat Key beach. 2 bedrooms with direct Gulf views, plus 2 lovely bathrooms. New kitchen cabinets, new quartz countertops, all new appliances. Lives like a single-family home as you don't have to ride an elevator or cover up to go to the

  Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228
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  $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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  $490,000 Sold Aug 01, 2025

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

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

  Last Sold Summary

  • 11% Below List Price
  • $528/SF
  • 51 Days On Market

  Current Estimated Value $485,131

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  2045 Gulf of Mexico Dr Unit M1514, Longboat Key, FL 34228
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  Est $921,259 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,336 Sq Ft

  4325 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  4325 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /39

  $610,000

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  528 Forest Way, Longboat Key, FL 34228

  Seize the opportunity to acquire a prime, elevated townhome in Cedars East on beautiful Longboat Key. This location is arguably the closest Cedars East property to the pristine, sugar-white sands of the Gulf. This Pet-friendly townhome is an Elevated structure, positioned well above the flood plain, ensuring peace of mind. The interior exudes sophistication, featuring stunning crown molding and

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  528 Forest Way, Longboat Key, FL 34228
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  /25

  $9,000 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; PRICE REDUCED!!! Available FEBRUARY - MARCH 2026!!! 30 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

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
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  $100,000 Sold Nov 24, 2025

  85 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $125/SF
  • 100 Days On Market

  Last Listing Agent Erica Smentowski KELLER WILLIAMS ON THE WATER S

  85 Twin Shores Blvd, Longboat Key, FL 34228
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft

  3710 Gulf of Mexico Dr Unit G27, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit G27, Longboat Key, FL 34228
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  $3,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,880 Sq Ft

  340 Gulf of Mexico Dr Unit 136, Longboat Key, FL 34228

  Two-level penthouse residences at Tangerine Bay Club are rarely available, and this south-facing corner offering sets a new benchmark for waterfront living. Recently reimagined, this nearly 3,000-square-foot residence captures expansive views of Sarasota Bay, the downtown skyline, and protected mangrove preserves, all while offering exceptional privacy. With two generous terraces, a private

  Roger Pettingell COLDWELL BANKER REALTY

  340 Gulf of Mexico Dr Unit 136, Longboat Key, FL 34228
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  /22

  $8,000 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. 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 and carpet, new kitchen appliances, three flat screen TVs with HD boxes

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  $17,500,000 Sold Nov 08, 2025

  6633 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 7 Beds
  • 10 Baths
  • 9,622 Sq Ft
  • Built 2013

  Last Sold Summary

  • 12% Below List Price
  • $1,819/SF
  • 0 Days On Market

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  6633 Gulf of Mexico Dr, Longboat Key, FL 34228
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  Est $805,882 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 427 Sq Ft

  3465 Gulf of Mexico Dr Unit 225, Longboat Key, FL 34228

  3465 Gulf of Mexico Dr Unit 225, Longboat Key, FL 34228

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