Longboat Key, FL Homes

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  $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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  /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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  $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 $268,345

  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 $728,418 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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  /35

  $1,299,000

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

  1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it

  Roger Pettingell COLDWELL BANKER REALTY

  1055 Gulf of Mexico Dr Unit 504, 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

  Current Estimated Value $725,322

  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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  /72

  $1,999,000

  • 3 Beds
  • 3 Baths
  • 2,122 Sq Ft

  775 Longboat Club Rd Unit 203, Longboat Key, FL 34228

  Welcome to your dream beachfront retreat, nestled behind the exclusive gates of the prestigious Longboat Key Club. This exquisite 3-bedroom, 3-bathroom Gulf-front residence captures breathtaking, unobstructed views of the sparkling turquoise waters of the Gulf from every room—an ever-changing canvas of sunlight, sea, and sky. From the moment you enter, you're greeted by expansive walls of glass

  Courtney Tarantino COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 203, Longboat Key, FL 34228
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  /69

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  Booking Now for the 2027 Season! Completely Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, 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 $306,787

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  549 Sutton Place, Longboat Key, FL 34228
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  /56

  Est $655,920 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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  /44

  $949,900

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

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors

  Donna Wrobel BERKSHIRE HATHAWAY HOMESERVICE

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /35

  $7,100 per month

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

  AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai

  Brenda Cozy COLDWELL BANKER REALTY

  3440 Gulf of Mexico Dr Unit 9, 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 $1,826,134

  Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  3322 Bayou Rd, Longboat Key, FL 34228
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  /51

  Est $336,278 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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  /52

  $975,000

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228

  Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228
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  /42

  $10,000 per month

  • 3 Beds
  • 3 Baths
  • 1,744 Sq Ft
  • House for Rent

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228

  Available beginning June 1st, 2026. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of

  Michael Cella CELLA'S REAL ESTATE INC

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /65

  $1,195,000 Sold Mar 10, 2025

  3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,555 Sq Ft
  • Built 1988

  Last Sold Summary

  • $468/SF
  • 30 Days On Market

  Current Estimated Value $1,128,292

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228
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  /42

  Est $348,048 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 809 Sq Ft

  102 Twin Shores Blvd, Longboat Key, FL 34228

  102 Twin Shores Blvd, Longboat Key, FL 34228
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  /76

  $2,790,000 Open House 2/15

  • 5 Beds
  • 5 Baths
  • 4,510 Sq Ft

  3408 Fair Oaks Ln, Longboat Key, FL 34228

  Elegant 5BR/5BA home in the gated community of Corey’s Landing within Bay Isles on Longboat Key. With over 4,500 sq ft, this spacious two-story residence offers open living areas, soaring ceilings, and refined design for both comfort and style. The light-filled great room with 22-ft ceilings opens to a gourmet kitchen with stone countertops, breakfast bar, and stainless-steel appliances. The

  Bruce Myer COLDWELL BANKER REALTY

  3408 Fair Oaks Ln, Longboat Key, FL 34228
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  /57

  $11,500 per month

  • 3 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • House for Rent

  2254 Harbour Court Dr, Longboat Key, FL 34228

  Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2254 Harbour Court Dr, Longboat Key, FL 34228
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  /2

  $1,025,000 Sold Feb 14, 2025

  1485 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,551 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $661/SF
  • 32 Days On Market

  Current Estimated Value $959,983

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  1485 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /60

  Est $738,505 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228
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  /55

  $3,245,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,330 Sq Ft

  5382 Sandhamn Place, Longboat Key, FL 34228

  Custom Key West inspired residence in the exclusive, gated enclave of Sandhamn Place. Perfectly positioned to capture the essence of coastal living, the property boasts direct Intracoastal Waterway access, expansive water vistas, and a deeded deep-water boat dock and lift on Sarasota Bay—an extraordinary combination of luxury and lifestyle. With over 5,000 sq. ft. of living and entertaining space

  Nora Johnson MICHAEL SAUNDERS & COMPANY

  5382 Sandhamn Place, Longboat Key, FL 34228
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  /40

  $12,000 per month

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

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

  Available for 2026 and 2027 Season!! Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
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  /2

  $2,200,000 Sold Jan 19, 2026

  548 Ketch Ln, Longboat Key, FL 34228

  • 2 Beds
  • 3 Baths
  • 2,273 Sq Ft
  • Built 1972

  Last Sold Summary

  • $968/SF
  • 0 Days On Market

  Last Listing Agent Kathy Callahan MICHAEL SAUNDERS & COMPANY

  548 Ketch Ln, Longboat Key, FL 34228
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  /53

  Est $642,690 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 896 Sq Ft

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228
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  /49

  $3,275,000

  • 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 turn-key furnished 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

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  595 Bowsprit Ln, Longboat Key, FL 34228
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  /59

  $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**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 section of Bay Isles, this

  Jennifer LeBlanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  /37

  $765,000 Sold Mar 13, 2025

  3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Built 1995

  Last Sold Summary

  • $600/SF
  • 7 Days On Market

  Current Estimated Value $725,602

  Last Listing Agent Lee Mirman INVESTMENTS IN SARASOTA

  3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228
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  /80

  Est $2,869,265 Not Listed For Sale

  • 2 Beds
  • 4.5 Baths
  • 2,965 Sq Ft

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228
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  /18

  $2,845,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,130 Sq Ft

  640 Lyons Ln, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Under Construction. Welcome to 640 Lyons Lane — a rare opportunity to purchase a brand-new, fully constructed home on one of North Longboat Key’s most distinctive streets. With homes on only one side and protected wetlands on the other, this location offers unmatched privacy, tranquil views, and a true coastal retreat. This listing includes a

  Adrian Johnson SEA BREEZE REAL ESTATE LLC

  640 Lyons Ln, Longboat Key, FL 34228
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  /13

  $3,000 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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  /2

  $760,000 Sold Jan 16, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $650/SF
  • 19 Days On Market

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228
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  /75

  Est $3,898,205 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,122 Sq Ft

  4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /38

  $1,149,000

  • 3 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces

  Ryan Ackerman COLDWELL BANKER REALTY

  350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228
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  /68

  $29,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • House for Rent

  591 Putting Green Ln, Longboat Key, FL 34228

  LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin

  Teresa Ribaudo JENNETTE PROPERTIES INC

  591 Putting Green Ln, Longboat Key, FL 34228
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  /2

  $2,700,400 Sold Jan 15, 2026

  598 Lyons Ln, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,276 Sq Ft
  • Built 2021

  Last Sold Summary

  • 8% Below List Price
  • $1,186/SF
  • 35 Days On Market

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  598 Lyons Ln, Longboat Key, FL 34228
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  /63

  Est $847,715 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,224 Sq Ft

  2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

  2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

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