Longboat Key, FL Homes

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  $2,400,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228

  Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2025, fee for each 30 day interest is

  Michael Moulton MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228
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  /15

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228

  Longboat Key vacation rental! You will love this wonderfully updated and tastefully furnished two-bedroom, two-bath third-floor condominium at the Beach Harbor Club. Located mid-key, this is a great resort-style community with deeded beach access just across the Gulf of Mexico, a beautiful heated community pool, access to the Bay for fishing and kayaking, and community grills and shuffleboard!

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
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  $340,000 Sold Nov 25, 2025

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 747 Sq Ft
  • Built 1969

  Last Sold Summary

  • $455/SF
  • 0 Days On Market

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228
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  /38

  Est $1,579,615 Not Listed For Sale

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

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228
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  /42

  $1,050,000

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft

  615 Dream Island Place Unit 105, Longboat Key, FL 34228

  Welcome to Paradise Found at Harbour Villa Club, a waterfront luxury condo that is truly a slice of heaven on earth. This stunning property offers breathtaking views of the glistening water and is situated in a prime location that is peaceful, serene, and truly one-of-a-kind. A true Longboat Key gem. As you step inside this luxurious fully renovated (2025) condo, you'll be greeted by a spacious

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  615 Dream Island Place Unit 105, Longboat Key, FL 34228
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  /35

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228

  2-bed, 2-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 211, Longboat Key, FL 34228
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  /2

  $1,190,000 Sold Sep 05, 2025

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,721 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $691/SF
  • 51 Days On Market

  Current Estimated Value $1,144,229

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /66

  Est $894,620 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  /17

  $275,000

  2600 Harbourside Dr Unit P-03, Longboat Key, FL 34228

  Easy in and out and close to parking! This 48 x 20 foot slip at Longboat Key Club Moorings is located on the north side of P-dock. 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 includes restaurants,

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit P-03, Longboat Key, FL 34228
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  /40

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • House for Rent

  573 Spanish Dr N, Longboat Key, FL 34228

  NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL ($4,600/MONTH). LEASE -3 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

  Norma Mladineo COLDWELL BANKER REALTY

  573 Spanish Dr N, Longboat Key, FL 34228
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  /2

  $1,750,000 Sold Oct 27, 2025

  6011 Emerald Harbor Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $907/SF
  • 0 Days On Market

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  6011 Emerald Harbor Dr, Longboat Key, FL 34228
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  /47

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 657 Sq Ft

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228
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  /94

  $549,900

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228

  Make your dreams come true with this beautiful waterfront condominium located at the popular Longboat Harbour resort! Enjoy gorgeous views of the water the moment you step in. This newly renovated 2BD/2BA second floor unit offers a roomy open floor plan with plenty of natural light, is being sold turnkey furnished. New Luxury Vinyl flooring and hurricane windows has been installed throughout. The

  Sandi Layfield MICHAEL SAUNDERS & COMPANY

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228
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  /12

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Condo for Rent

  540 Neptune Ave Unit 7, Longboat Key, FL 34228

  Iconic... Gulf Key.This immaculate, newly renovated two-bedroom, two-bath villa is just a three-minute walk to the beach. Gulf Key invites you to slow down, breathe in the salt air, and truly unwind. It’s classic clay tile roof and stucco exterior reflect understated elegance and the essence of an OLD Florida lifestyle. With only 10 units, Gulf Key offers peace and privacy in a stellar

  Pamala Casey CASEY REALTY CORPORATION

  540 Neptune Ave Unit 7, Longboat Key, FL 34228
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  /2

  $357,000 Sold Dec 19, 2025

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 837 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $427/SF
  • 22 Days On Market

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228
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  /52

  Est $793,644 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /90

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 2,317 Sq Ft

  690 Jungle Queen Way, Longboat Key, FL 34228

  LONGBOAT KEY HOME WITH WATER VIEWS. BEST PRICE PER SQ FT! Attention boating enthusiasts! Sailboat waterfront home in Longboat Key with Florida's favorite southern exposure. Park your boat on the stationary, or floating dock with a boat lift, 10,000 pounds boat lift, NEW seawall 125 ft., stainless ladder and fillet station. The outdoor kitchen is paved with a cedar pergola, a firepit, kitchen

  Reeny Kaney RE/MAX ALLIANCE GROUP

  690 Jungle Queen Way, Longboat Key, FL 34228
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  /83

  $25,000 per month

  • 1 Bed
  • 1.5 Baths
  • 1,721 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /2

  $1,000,000 Sold Jul 01, 2025

  230 Sands Point Rd Unit 3501, Longboat Key, FL 34228

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

  Last Sold Summary

  • 13% Below List Price
  • $1,333/SF
  • 58 Days On Market

  Current Estimated Value $995,406

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  230 Sands Point Rd Unit 3501, Longboat Key, FL 34228
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  /28

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 720 Sq Ft

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228
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  /48

  $335,000

  • 2 Beds
  • 2 Baths
  • 1,278 Sq Ft

  534 Sutton Place Unit 534, Longboat Key, FL 34228

  GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience island living on Longboat Key. Ideally located just steps from private Gulf Beach access, this 2 bedroom, 2 bathroom condo offers both comfort and convenience for your winter getaway or year-round living. The spacious, open-concept living and dining area flows seamlessly into

  Tanner Frey KELLER WILLIAMS ON THE WATER S

  534 Sutton Place Unit 534, Longboat Key, FL 34228
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  /31

  $10,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /2

  $600,000 Sold Dec 08, 2025

  780 Jungle Queen Way, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 1,242 Sq Ft
  • Built 1962

  Last Sold Summary

  • 29% Below List Price
  • $483/SF
  • 207 Days On Market

  Last Listing Agent Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  780 Jungle Queen Way, Longboat Key, FL 34228
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  /43

  Est $659,993 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
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  /53

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228

  A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seaplace with no shared walls, offering unparalleled privacy and tranquility. Fully remodeled in 2019, the home features a designer kitchen with quartz countertops, custom cabinetry and premium appliances, seamlessly complemented by elegant soft grey laminate hardwood flooring throughout. A spacious lanai spans

  Rita Pogany PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228
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  /69

  $25,000 per month

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

  690 Old Compass Rd, Longboat Key, FL 34228

  Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

  Teresa Ribaudo JENNETTE PROPERTIES INC

  690 Old Compass Rd, Longboat Key, FL 34228
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  /2

  $275,000 Sold Jun 16, 2025

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • 23 Days On Market

  Current Estimated Value $269,983

  Last Listing Agent Jessica Hurley PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228
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  /78

  Est $745,142 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft

  4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /48

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,491 Sq Ft

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228

  Ultra-luxury, fully remodeled Gulf-front residence on Longboat Key. This sixth-floor, move-in ready condominium at Islands West showcases imported Italian cabinetry, level 5 drywall, Carrara marble flooring, aqua quartz countertops and steam shower. All-new hurricane-impact windows and doors, including floor-to-ceiling glass in both bedrooms, frame sweeping water views and a desirable southern

  Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228
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  /52

  $19,975 per month

  • 4 Beds
  • 4 Baths
  • 4,236 Sq Ft
  • House for Rent

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228

  Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows

  Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /2

  $738,000 Sold Oct 14, 2025

  5055 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 1973

  Last Sold Summary

  • 33% Below List Price
  • $497/SF
  • 186 Days On Market

  Last Listing Agent Bo Fuller FULLER GROUP

  5055 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  /25

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 676 Sq Ft

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228
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  /66

  $1,065,000

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228

  Bring your boat to Longboat Key. Fully furnished second floor corner unit with boat dock and stunning views of the Sarasota Bay in beautiful Harbor Villa Club. This beautifully renovated 2-bedroom, 2-bathroom condo is an incredible opportunity to live right on the Sarasota bay with 180 degree breathtaking water views. This single level, corner unit has plenty of natural light and has been updated

  Greg Orquera ORQUERA FLORIDA INVESTMENTS

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228
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  /73

  $10,000 per month

  • 6 Beds
  • 5.5 Baths
  • 4,676 Sq Ft
  • House for Rent

  614 Norton St, Longboat Key, FL 34228

  Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle.Key Features:-Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the

  Miranda Platt, PA RELAX REALTY GROUP INC

  614 Norton St, Longboat Key, FL 34228
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  /2

  $310,000 Sold Apr 14, 2025

  549 Sutton Place, Longboat Key, FL 34228

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1972

  Last Sold Summary

  • 22% Below List Price
  • $308/SF
  • 89 Days On Market

  Current Estimated Value $314,758

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  549 Sutton Place, Longboat Key, FL 34228
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  /56

  Est $662,501 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228
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  /67

  $1,695,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  3060 Grand Bay Blvd Unit 154, Longboat Key, FL 34228

  Under contract-accepting backup offers. Beautifully renovated and offered turnkey furnished, this 3BR/3.5BA residence is perfectly positioned on the 5th floor of Building I in Grand Bay on Longboat Key. A private elevator opens to an elegant, open layout with new wood floors, architectural details, and recessed lighting. Walls of glass frame sweeping views of Sarasota Bay and the Harbourside golf

  Bruce Myer COLDWELL BANKER REALTY

  3060 Grand Bay Blvd Unit 154, Longboat Key, FL 34228
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  /56

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Condo for Rent

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228

  Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right behind the

  Jorge Perez ROI AVE LLC

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228
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  /2

  $1,825,000 Sold Aug 26, 2025

  3322 Bayou Rd, Longboat Key, FL 34228

  • 5 Beds
  • 3 Baths
  • 3,441 Sq Ft
  • Built 1982

  Last Sold Summary

  • 20% Below List Price
  • $530/SF
  • 111 Days On Market

  Current Estimated Value $1,826,128

  Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  3322 Bayou Rd, Longboat Key, FL 34228
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  /51

  Est $321,818 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 741 Sq Ft

  104 Twin Shores Blvd, Longboat Key, FL 34228

  104 Twin Shores Blvd, Longboat Key, FL 34228

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