Longboat Key, FL Homes

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  $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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  /53

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Condo for Rent

  840 Bayport Way Unit 840, Longboat Key, FL 34228

  This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

  Shirley Cuddy REALTY SERVICES INC

  840 Bayport Way Unit 840, Longboat Key, FL 34228
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  $1,070,000 Sold Jul 31, 2025

  4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

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

  Last Sold Summary

  • 30% Below List Price
  • $814/SF
  • 425 Days On Market

  Current Estimated Value $1,046,153

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

  4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /47

  Est $1,765,364 Not Listed For Sale

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

  2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /53

  $775,000 Pending

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

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228

  Under contract-accepting backup offers. Set in the sought-after Longbeach community on the northern end of Longboat Key, this beautifully updated, Turnkey Furnished 2BR/2BA residence blends comfort, elegance and effortless Gulfside living. Poised on the second floor, it enjoys picturesque views over the community’s manicured landscape and out toward the shimmering waters of the Gulf. Inside, over

  Bruce Myer COLDWELL BANKER REALTY

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228
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  /45

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Condo for Rent

  1930 Harbourside Dr Unit 134, Longboat Key, FL 34228

  GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
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  $8,927,000 Sold Jan 03, 2025

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

  • 4 Beds
  • 5.5 Baths
  • 5,320 Sq Ft
  • Built 2024

  Last Sold Summary

  • $1,678/SF
  • 0 Days On Market

  Last Listing Agent Lynn Morris MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
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  /25

  Est $830,043 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
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  /100

  $2,950,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,276 Sq Ft

  598 Lyons Ln, Longboat Key, FL 34228

  Experience the pinnacle of coastal luxury in this exceptional custom estate, completed in 2021 by renowned Mason Martin Builders. Designed and sparingly used by the original owners who crafted it with precision and care, this like-new residence has since been thoughtfully reimagined by the current owner with an elevated level of designer finishes and enhancements throughout. Situated near the

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  598 Lyons Ln, Longboat Key, FL 34228
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  /38

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228

  Steps from the Sand – Luxury Beach Condo with Pool Access!Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits!Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community

  nicoletta buonaccordo ALTIS REALTY

  3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
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  $752,000 Sold Apr 17, 2025

  1930 Harbourside Dr Unit 152, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $631/SF
  • 123 Days On Market

  Current Estimated Value $697,995

  Last Listing Agent Rae Hayo AN ISLAND PLACE REALTY INC

  1930 Harbourside Dr Unit 152, Longboat Key, FL 34228
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  /29

  Est $1,163,231 Not Listed For Sale

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

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /71

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  2675 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

  HUGE PRICE REDUCTION of $105,000, it's very rare to find gorgeous full gulf views at this price point on Longboat Key. Veinte (20 in Spanish) is a luxury condominium community with only twenty residents located on beautiful and unique Longboat Key. Magnificent direct gulf views from all main rooms; electric hurricane shutters on lanai and bedrooms, electric screen on the lanai and custom shades

  Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
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  /34

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  2-bed, 2-bath seasonal or annual 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

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  $395,000 Sold Jan 10, 2025

  610 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft
  • Built 1965

  Last Sold Summary

  • $328/SF
  • 9 Days On Market

  Current Estimated Value $459,648

  Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  610 Fox St, Longboat Key, FL 34228
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  /13

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  17 Main Street Dr, Longboat Key, FL 34228

  17 Main Street Dr, 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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  /31

  $3,900 per month

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

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

  Open now through end of January. Have your holidays on the Key with HEATED POOL, amazing sunsets, perfect tennis weather and the pristine beach just steps away. This well appointed and updated condo with an open open, split floor plan has plenty of space and a huge screened lanai that spans the entire unit. The primary bedroom has TWO KING SIZED beds, a huge walk-in closet and ensuite bath. The

  Rosemarie McKee COLDWELL BANKER REALTY

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
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  $2,500,000 Sold May 23, 2025

  3606 Fair Oaks Place, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 3,842 Sq Ft
  • Built 2000

  Last Sold Summary

  • 23% Below List Price
  • $651/SF
  • 85 Days On Market

  Current Estimated Value $2,436,917

  Last Listing Agent Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3606 Fair Oaks Place, Longboat Key, FL 34228
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  /32

  Est $899,039 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228
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  /64

  $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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  /39

  $10,500 per month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Condo for Rent

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

  **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach,

  Norma Mladineo COLDWELL BANKER REALTY

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
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  $535,000 Sold Oct 29, 2025

  640 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $429/SF
  • 168 Days On Market

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  640 Fox St, Longboat Key, FL 34228
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  /54

  Est $806,429 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,453 Sq Ft

  5265 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  5265 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /31

  $3,595,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft

  600 Dream Island Rd, Longboat Key, FL 34228

  Double lot on a wide canal that is 1.06 acres with 200 ft of protected waterfront located on Dream Island Road Longboat Key. This tranquil waterfront retreat is ready for your new home plus the possibility of two canal front homes. For the boating enthusiast, the intracoastal waterway is easily accessible with no bridges. This oasis is a waterfront paradise. There is a 4 bedroom 3 bath home on

  Reid Murphy DEVELOPERS REALTY LBK, INC

  600 Dream Island Rd, Longboat Key, FL 34228
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  /35

  $6,500 per month

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

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  AVAILABLE Jan - Mar 2026!!! : 1 month minimum. Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  $1,800,000 Sold Jun 30, 2025

  612 Weston Pointe Ct, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,612 Sq Ft
  • Built 1993

  Last Sold Summary

  • 10% Below List Price
  • $689/SF
  • 80 Days On Market

  Current Estimated Value $1,715,452

  Last Listing Agent Cindy Schatzle COLDWELL BANKER REALTY

  612 Weston Pointe Ct, Longboat Key, FL 34228
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  /35

  Est $541,978 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft

  3330 Gulf of Mexico Dr Unit 106-D, Longboat Key, FL 34228

  3330 Gulf of Mexico Dr Unit 106-D, Longboat Key, FL 34228
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  /48

  $1,300,000

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

  7125 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228

  Experience coastal living at its finest in this beautifully remodeled beachfront condo! This stunning residence features brand new, tastefully selected furniture and a modern, elegant design throughout. Enjoy breathtaking ocean views and unforgettable sunsets from your private west-facing balcony. Perfectly positioned on the beach, this home offers the ideal blend of luxury, comfort, and seaside

  Luziele Dearaujo Realty 100

  7125 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

  AVAILABLE ONLY FOR AFTER APRIL 2026 SEASON! MINIMUM 2 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give

  Brigette Marcus NEXTHOME EXCELLENCE

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
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  $252,000 Sold Apr 17, 2025

  812 Spanish Dr S Unit 89, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft
  • Built 1969

  Last Sold Summary

  • 23% Below List Price
  • $190/SF
  • 120 Days On Market

  Current Estimated Value $346,923

  Last Listing Agent Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  812 Spanish Dr S Unit 89, Longboat Key, FL 34228
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  /45

  Est $4,609,644 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,640 Sq Ft

  4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228

  4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228
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  /43

  $895,000

  • 2 Beds
  • 2 Baths
  • 1,413 Sq Ft

  3080 Grand Bay Blvd Unit 533, Longboat Key, FL 34228

  As you step into this rarely available Capri floor plan, the entrance sets the stage for an exquisite bayfront experience. Inside, the residence unfolds with white ceramic tile throughout and water views via floor-to-ceiling windows and sliders in every room, creating a bright, private ambiance and a seamless connection to the natural beauty that surrounds you. The 2 large balconies immediately

  Ryan Ackerman COLDWELL BANKER REALTY

  3080 Grand Bay Blvd Unit 533, Longboat Key, FL 34228
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  /51

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Condo for Rent

  5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor

  Scott Nold TNG PROPERTY MANAGEMENT

  5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  $1,400,000 Sold Aug 25, 2025

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228

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

  Last Sold Summary

  • 15% Below List Price
  • $1,134/SF
  • 149 Days On Market

  Current Estimated Value $1,313,145

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228
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  /37

  Est $285,421 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 712 Sq Ft

  3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228

  3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228
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  /36

  $938,500

  • 2 Beds
  • 2.5 Baths
  • 2,394 Sq Ft

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

  Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  350 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
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  /76

  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft
  • Condo for Rent

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

  C. Alison Hunter JENNETTE PROPERTIES INC

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  $2,000,000 Sold Oct 15, 2025

  4 Winslow Place, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 3,288 Sq Ft
  • Built 1963

  Last Sold Summary

  • $608/SF
  • 0 Days On Market

  Last Listing Agent Kaisen Mitchell COLDWELL BANKER REALTY

  4 Winslow Place, Longboat Key, FL 34228
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  /19

  Est $326,141 Not Listed For Sale

  • Studio
  • 1,820 Sq Ft

  2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228

  2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228

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