Longboat Key, FL Homes

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  $1,000,000

  • Land
  • 19,166 Sq Ft
  • $2,272,727 per Acre

  6604 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 three 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

  6604 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $2,500 Per Month

  • 1 Bed
  • 1 Bath
  • 721 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

  1-bed, 1-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 E205, Longboat Key, FL 34228
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  $475,000 Sold Jul 25, 2025

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 1969

  Last Sold Summary

  • 32% Below List Price
  • $330/SF
  • 163 Days On Market

  Current Estimated Value $483,386

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228
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  Est $1,471,833 Not Listed For Sale

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,839 Sq Ft
  • Built 1981

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Below List Price
  • $843/SF
  • 39 Days On Market

  • Last Sold Price $1,550,000
  • Jun 05, 2024

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  $500,000

  • Land
  • 1 Acre
  • $500,000 per Acre

  2600 Harbourside Dr Unit B-13, Longboat Key, FL 34228

  An easy access slip with the views to along with the superb amenity package, Slip B-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. The Longboat

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit B-13, Longboat Key, FL 34228
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  $30,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,230 Sq Ft
  • House for Rent

  6925 Longboat Dr S, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  6925 Longboat Dr S, Longboat Key, FL 34228
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  $950,000 Sold Mar 18, 2026

  2323 Harbour Oaks Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $397/SF
  • 108 Days On Market

  Current Estimated Value $992,299

  Last Listing Agent Steven Moore MICHAEL SAUNDERS & COMPANY

  2323 Harbour Oaks Dr, Longboat Key, FL 34228
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  Est $813,346 Not Listed For Sale

  750 Saint Judes Dr N, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1958

  750 Saint Judes Dr N, Longboat Key, FL 34228

  Last Sold Summary

  • 36% Above List Price
  • $482/SF
  • 134 Days On Market

  • Last Sold Price $600,000
  • Jan 04, 2025

  Last Listing Agent Chevon Eaton CHEVON EATON
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  /88

  $1,899,000

  • 4 Beds
  • 2.5 Baths
  • 3,009 Sq Ft

  3040 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228

  Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St.

  Frank Lambert PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3040 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
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  $11,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • House for Rent

  3390 Bayou Sound, Longboat Key, FL 34228

  **This is a 2 month minimum vacation rental** Booked January-March 2027 Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou part of Bay

  Jennifer Le Blanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  $1,175,000 Sold Feb 20, 2026

  747 Marbury Ln, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,353 Sq Ft
  • Built 1968

  Last Sold Summary

  • 18% Below List Price
  • $499/SF
  • 72 Days On Market

  Current Estimated Value $1,249,097

  Last Listing Agent Michael Busch COLDWELL BANKER REALTY

  747 Marbury Ln, Longboat Key, FL 34228
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  Est $7,908,285 Not Listed For Sale

  60 Lighthouse Point Dr, Longboat Key, FL 34228

  • 5 Beds
  • 8 Baths
  • 7,170 Sq Ft
  • Built 2000

  60 Lighthouse Point Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 22% Below List Price
  • $1,416/SF
  • 185 Days On Market

  • Last Sold Price $10,150,000
  • Sep 11, 2024

  Last Listing Agent Candy Swick CANDY SWICK & COMPANY
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  $1,250,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  615 Buttonwood Dr, Longboat Key, FL 34228

  Under contract-accepting backup offers. It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot

  Walter Hackett PREMIER SOTHEBY'S INTERNATIONAL REALTY

  615 Buttonwood Dr, Longboat Key, FL 34228
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  $17,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  613 Buttonwood Dr, Longboat Key, FL 34228

  Available for season 2027Looking for a 3 month rental. Newly renovated, this beautiful home features a split floor plan with generously sized bedrooms and walk-in closets, all enhanced by a charming coastal flair. The kitchen—truly the heart of the home—is fully equipped with everything you need to prepare delicious home-cooked meals. Enjoy your morning coffee or an evening cocktail in the

  Jennifer Le Blanc PRECISE REALTY CORP

  613 Buttonwood Dr, Longboat Key, FL 34228
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  $1,420,000 Sold Aug 13, 2025

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,410 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $589/SF
  • 104 Days On Market

  Current Estimated Value $1,497,996

  Last Listing Agent Stacy Hanan MICHAEL SAUNDERS & COMPANY

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

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

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

  Last Sold Summary

  • $392/SF
  • 0 Days On Market

  • Last Sold Price $345,000
  • Feb 28, 2024

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $10,500,000

  • 5 Beds
  • 5 Baths
  • 5,982 Sq Ft

  600 Putter Ln, Longboat Key, FL 34228

  Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the

  Kathleen Callender FLORIDA CAPITAL REALTY

  600 Putter Ln, Longboat Key, FL 34228
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  $2,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Condo for Rent

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis,

  Annabelle Newland STOCKTON REALTY ADVISORS LLC

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  $1,600,000 Sold May 01, 2026

  1135 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,065/SF
  • 44 Days On Market

  Current Estimated Value $1,617,283

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  1135 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
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  Est $3,831,463 Not Listed For Sale

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  • 3 Beds
  • 5 Baths
  • 3,400 Sq Ft
  • Built 1996

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Last Sold Summary

  • 4% Below List Price
  • $1,176/SF
  • 278 Days On Market

  • Last Sold Price $4,000,000
  • Dec 16, 2024

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
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  $3,175,000

  • 4 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  595 Bowsprit Ln, Longboat Key, FL 34228

  Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this 4-bedroom, 2.5-bath home, effective year 2016, in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  595 Bowsprit Ln, Longboat Key, FL 34228
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  $2,500 Per Month

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

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228

  LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
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  $4,237,500 Sold Apr 30, 2026

  435 L Ambiance Dr Unit J703, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft
  • Built 1994

  Last Sold Summary

  • 12% Below List Price
  • $1,503/SF
  • 154 Days On Market

  Current Estimated Value $4,340,555

  Last Listing Agent jeffrey Rhinelander COLDWELL BANKER REALTY

  435 L Ambiance Dr Unit J703, Longboat Key, FL 34228
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  Est $1,525,279 Not Listed For Sale

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Built 1984

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  Last Sold Summary

  • 12% Below List Price
  • $705/SF
  • 0 Days On Market

  • Last Sold Price $1,735,000
  • Feb 09, 2024

  Last Listing Agent Terri Thacker Michael Saunders
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  $300,000

  2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228

  A favorite dock in the Marina with ample turning radius. This 55 x 21 foot slip at Longboat Key Club Moorings is located on the west side of the Marina. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228
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  $10,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Condo for Rent

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

  C. Alison Hunter JENNETTE PROPERTIES INC

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
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  $108,000 Sold Sep 30, 2025

  72 Main Street Dr, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1965

  Last Sold Summary

  • $138/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  72 Main Street Dr, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 693 Sq Ft
  • Built 2007

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

  Last Sold Summary

  • $433/SF
  • 61 Days On Market

  • Last Sold Price $300,000
  • Apr 17, 2024

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $1,650,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  524 Ketch Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  524 Ketch Ln, Longboat Key, FL 34228
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  $5,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228

  Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights*Direct

  Donna Channey WAGNER REALTY

  1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
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  $1,465,000 Sold Aug 28, 2025

  501 Reclinata Dr, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,784 Sq Ft
  • Built 2002

  Last Sold Summary

  • 18% Below List Price
  • $526/SF
  • 160 Days On Market

  Current Estimated Value $1,558,498

  Last Listing Agent Barbara Najmy STARZ REAL ESTATE, LLC

  501 Reclinata Dr, Longboat Key, FL 34228
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  Est $807,680 Not Listed For Sale

  5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,498 Sq Ft
  • Built 1974

  5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  Last Sold Summary

  • 2% Above List Price
  • $527/SF
  • 58 Days On Market

  • Last Sold Price $790,000
  • Apr 19, 2024

  Last Listing Agent Jens Pinkernell DOUGLAS ELLIMAN
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  $625,000

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft

  3080 Grand Bay Blvd Unit 515, Longboat Key, FL 34228

  Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and

  Bruce Myer COLDWELL BANKER REALTY

  3080 Grand Bay Blvd Unit 515, Longboat Key, FL 34228
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  /31

  $5,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

  AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
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  $1,425,000 Sold Mar 26, 2026

  1445 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,859 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $767/SF
  • 177 Days On Market

  Current Estimated Value $1,462,206

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  Est $2,289,713 Not Listed For Sale

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1982

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

  Last Sold Summary

  • 16% Below List Price
  • $2,113/SF
  • 6 Days On Market

  • Last Sold Price $2,712,500
  • Dec 29, 2023

  Last Listing Agent Ian Addy, PA Michael Saunders
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  $485,000

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  605 Sutton Place Unit 102, Longboat Key, FL 34228

  Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  605 Sutton Place Unit 102, Longboat Key, FL 34228
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  /31

  $9,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

  Available March 2026. Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a

  Shaun Cumston STERLING REALTY

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
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  $1,400,000 Sold Dec 03, 2025

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 6 Days On Market

  Current Estimated Value $1,395,424

  Last Listing Agent Ellen Kirkegaard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /29

  Est $1,196,339 Not Listed For Sale

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,859 Sq Ft
  • Built 1982

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  Last Sold Summary

  • $646/SF
  • 155 Days On Market

  • Last Sold Price $1,200,000
  • May 22, 2024

  Last Listing Agent Jonathan Fox Michael Saunders

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