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Longboat Key Homes & Condos

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Longboat Key

Take a ride on Gulf of Mexico Drive, Cortez south to St. Armand's Circle, and you will understand why Longboat Key is a destination for travelers and called home by many.  Spanning Manatee and Sarasota County, Longboat Key is a barrier island between Sarasota Bay and the turquoise waters of the Gulf of Mexico.  Longboat Key is home to 2 championship golf courses at Longboat Key Club.  Waterfront Homes, Boating Communities, Condos - you will find it all here.  Longboat Key living is truly paradise.

 

New Listings

615 Dream Island Road Unit 304, Longboat Key image
615 Dream Island Road Unit 304, Longboat Key — 615 $840,000

Welcome to Longboat Key! Twelve miles of beaches have helped to make this a luxury Gulf Coast resort community. This beautifully updated 2-bedroom, 2-bathroom, 1,293 sf...

  • 2 Beds
  • 2 Baths
  • Harbour Villa Club At The Bucc SubDv.
  • 34228 Zip Code
4500 Gulf Of Mexico Drive Unit PH4, Longboat Key image
4500 Gulf Of Mexico Drive Unit PH4, Longboat Key — G $875,000

Windward Bay is a beautiful waterfront condo property located in Longboat Key, Florida. This 2 bedroom, 2 bath condo sits directly on the water’s edge of sparkling Saraso...

  • 2 Beds
  • 2 Baths
  • Windward Bay SubDv.
  • 34228 Zip Code
505 Forest Way Unit 6, Longboat Key image
505 Forest Way Unit 6, Longboat Key — 505 $640,000

This meticulously maintained condo in Cedars East is being offered FULLY furnished, and is a turn-key income producing property just across the street from Gulf-front bea...

  • 2 Beds
  • 2.5 Baths
  • Cedars East SubDv.
  • 34228 Zip Code
1904 Harbourside Drive Unit 204, Longboat Key image
1904 Harbourside Drive Unit 204, Longboat Key — Fairway Bay/1904 $1,195,000

From its full list of updates to its amenity-rich lifestyle, this 3BR/3BA corner townhouse in Fairway Bay presents an unparalleled opportunity complemented by a sought-af...

  • 3 Beds
  • 3 Baths
  • Fairway Bay SubDv.
  • 34228 Zip Code
605 Spanish Drive N, Longboat Key image
605 Spanish Drive N, Longboat Key $699,900

PROFESSIONAL PICTURES COMING SOON! Enjoy the natural setting from this well-appointed and updated private stand-alone Villa in the exclusive neighborhood of Spanish Main...

  • 2 Beds
  • 2 Baths
  • Spanish Main Yacht Club SubDv.
  • 34228 Zip Code
3633 Fair Oaks Place, Longboat Key image
3633 Fair Oaks Place, Longboat Key $1,925,000

Enjoy Sunsets and a lifestyle of luxury on Longboat Key in this maintenance-free courtyard-style home in Queens Harbour. One of the most sought-after communities on Longb...

  • 3 Beds
  • 3.5 Baths
  • Bay Isles SubDv.
  • 34228 Zip Code
601 Longboat Club Road Unit 302S, Longboat Key image
601 Longboat Club Road Unit 302S, Longboat Key — Longboat Key Towers $1,750,000

Within the gates of the Longboat Key Club Islandside, the beach is your backyard, and the golf course is in your front yard. This residence is a WOW! When you enter thi...

  • 2 Beds
  • 2 Baths
  • Longboat Key Towers SubDv.
  • 34228 Zip Code
4350 Chatham Drive Unit 108, Longboat Key image
4350 Chatham Drive Unit 108, Longboat Key — E / 4350 $749,000 ▼

Rare opportunity! Beautifully updated and furnished ground-floor end-unit with tranquil harbor views and fabulous beach resort lifestyle. Enjoy carefree coastal living wi...

  • 2 Beds
  • 2 Baths
  • Longboat Harbour North SubDv.
  • 34228 Zip Code
3080 Grand Bay Boulevard Unit 522, Longboat Key image
3080 Grand Bay Boulevard Unit 522, Longboat Key — Grand Bay 5 $989,000

Grand Bay, turn-key furnished and move-in ready, or renovate and make it your own. Beautiful bay views from the large, wrap around terrace and an amenity rich community,...

  • 2 Beds
  • 2 Baths
  • Grand Bay SubDv.
  • 34228 Zip Code
700 Lyons Lane, Longboat Key image
700 Lyons Lane, Longboat Key $4,100,000

CASUAL ELEGANCE best describes this LUXURY, WATERFRONT HOME on LONGBOAT KEY! The BEST OF ALL WORLDS with EXPANSIVE BAY VIEWS in the front, DEEP WATER BOATING in the back ...

  • 4 Beds
  • 3.5 Baths
  • Sleepy Lagoon SubDv.
  • 34228 Zip Code
4401 Gulf Of Mexico Drive Unit 201, Longboat Key image
4401 Gulf Of Mexico Drive Unit 201, Longboat Key — N/A $1,175,000

SUNSETS AND SALTSPRAY...Sound a little like YOUR PIECE OF PARADISE...and that's exactly what it could be!!! Located ON the white sand beaches of LONGBOAT KEY this amazing...

  • 2 Beds
  • 2 Baths
  • Longboat Harbour Towers SubDv.
  • 34228 Zip Code
4425 Gulf Of Mexico Drive Unit 102E, Longboat Key image
4425 Gulf Of Mexico Drive Unit 102E, Longboat Key — Laplaya $569,000

Bright and sunny 2 bedroom & 1 bathroom, end unit at LaPlaya Gulf Front Condominium. Great Home Away from Home ! Just few steps from the door you will enjoy 200 feet of s...

  • 2 Beds
  • 1 Baths
  • La Playa SubDv.
  • 34228 Zip Code
2425 Gulf Of Mexico Drive Unit 8F, Longboat Key image
2425 Gulf Of Mexico Drive Unit 8F, Longboat Key — Sea Gate $1,999,000

These beach and water views seem to go on forever. This 8th floor 2 bedroom 2 bath home puts you just high enough to get the incredible water views yet low enough to sti...

  • 2 Beds
  • 2 Baths
  • Sea Gate Club SubDv.
  • 34228 Zip Code
5444 Gulf Of Mexico Drive, Longboat Key image
5444 Gulf Of Mexico Drive, Longboat Key $7,850,000

Stunning contemporary bayfront home on Longboat Key with unrivalled panoramic penthouse like views of Sarasota Bay, downtown Sarasota, and nature preserve. Adjacent to a...

  • 5 Beds
  • 5 Baths
  • Cedar Woodlands SubDv.
  • 34228 Zip Code
501 Harbor Gate Way, Longboat Key image
501 Harbor Gate Way, Longboat Key $2,995,000

One or more photo(s) has been virtually staged. Discover next-level grandeur, serenity and privacy in this 3BR plus den/office, 3,662+/- sq.-ft. canal-front residence in ...

  • 3 Beds
  • 3.5 Baths
  • Bay Isles SubDv.
  • 34228 Zip Code
565 Sanctuary Drive Unit B505, Longboat Key image
565 Sanctuary Drive Unit B505, Longboat Key — Sanctuary $2,575,000

Opportunity to own a fifth floor Gulf front Sanctuary residence ready to be remolded to your personal specs. The condominium floor plan features 3 bedroom, 2 1/2 baths w...

  • 3 Beds
  • 2.5 Baths
  • Sanctuary SubDv.
  • 34228 Zip Code
3532 Fair Oaks Lane, Longboat Key image
3532 Fair Oaks Lane, Longboat Key $1,800,000

Spacious and comfortable in coveted Queens Harbour. Located behind the gates of Longboat Key's Bay Isles section, this Taylor Woodrow built Essex model centers around a p...

  • 4 Beds
  • 4.5 Baths
  • Queens Harbour (F/K/A Manchester Bay) SubDv.
  • 34228 Zip Code
4725 Gulf Of Mexico Drive Unit 213, Longboat Key image
4725 Gulf Of Mexico Drive Unit 213, Longboat Key — 13 $869,000

Don’t miss the opportunity to own this 2 bedroom vacation getaway, which earned over $63K in gross income for 2021, at the popular beachside community of Sand Cay. This f...

  • 2 Beds
  • 2 Baths
  • Sand Cay A Condominium SubDv.
  • 34228 Zip Code
519 Rountree Drive, Longboat Key image
519 Rountree Drive, Longboat Key $2,595,000

BUILD YOUR DREAM HOME! At the top of any Florida waterfront property wish list, are locations with Gulf views, convenient beach access and private boat docks. 519 Rountre...

  • 3 Beds
  • 2 Baths
  • Longboat Key Estates SubDv.
  • 34228 Zip Code
5440 Gulf Of Mexico Drive, Longboat Key image
5440 Gulf Of Mexico Drive, Longboat Key $5,050,000

Wonderful opportunity on beautiful Longboat Key. Tranquil, peaceful, private setting next to Durante Park. Building land for 6 homes with deeded beach access to the wo...

  • Cedar Woodlands SubDv.
  • 34228 Zip Code
536 General Harris Street, Longboat Key image
536 General Harris Street, Longboat Key $2,395,000

A once in a lifetime opportunity to own a unique property on Longboat Key, which is an exclusive island that spans almost 11 miles on the beautiful sparkling shores of th...

  • Sleepy Lagoon Add SubDv.
  • 34228 Zip Code
2600 Harbourside Drive Unit Q-1, Longboat Key image
2600 Harbourside Drive Unit Q-1, Longboat Key $250,000

Enjoy all the amenities of the private Longboat Key Club as a Club Member at this 45 x 21 ft slip. Direct access to Sarasota Bay and the ICW. The deep water marina is as ...

  • Bay Isles SubDv.
  • 34228 Zip Code
583 Spanish Drive S Unit 129, Longboat Key image
583 Spanish Drive S Unit 129, Longboat Key $895,000

Looking for a piece of paradise on the Suncoast of Florida? Don’t miss the opportunity to own this rare standalone villa that lives like a single-family private home, in ...

  • 2 Beds
  • 2 Baths
  • Spanish Main Yacht Club SubDv.
  • 34228 Zip Code
4325 Gulf Of Mexico Drive Unit 304, Longboat Key image
4325 Gulf Of Mexico Drive Unit 304, Longboat Key $1,300,000

Welcome to Tiffany Plaza, a mid-rise with only 41 units. Spectacular full Gulf views from all common areas, including master bedroom. This spacious open floor plan has th...

  • 3 Beds
  • 2.5 Baths
  • Tiffany Place SubDv.
  • 34228 Zip Code
3414 Fair Oaks Lane, Longboat Key image
3414 Fair Oaks Lane, Longboat Key $2,295,000

Revel in the spaciousness, spectacular lifestyle and serenity of golf course and bay views in this sprawling 4BR/4BA home in Corey’s Landing, a sought-after, maintenance-...

  • 4 Beds
  • 4 Baths
  • Coreys Landing SubDv.
  • 34228 Zip Code
597 Bayview Drive, Longboat Key image
597 Bayview Drive, Longboat Key $2,750,000

Lush tropical flora and fauna embrace exceptional quality and comfort on a superb waterfront location. Presenting a remarkable renovation, this casually sophisticated Key...

  • 3 Beds
  • 3 Baths
  • Bayview Estates SubDv.
  • 34228 Zip Code
2600 Harbourside Drive Unit L-08, Longboat Key image
2600 Harbourside Drive Unit L-08, Longboat Key $475,000

One of the best views from this slip in the marina is this 82 ft x 26 ft slip. Finger pier is 32 ft. Enjoy all the amenities of the private Longboat Key Club as a Yacht C...

  • Bay Isles SubDv.
  • 34228 Zip Code
2045 Gulf Of Mexico Drive Unit M1-112, Longboat Key image
2045 Gulf Of Mexico Drive Unit M1-112, Longboat Key — 2045 $1,750,000

This beautiful & bright updated three bedroom, two bath condominium with direct gulf views is coming furnished with the exclusion of art work & pictures. Located on the f...

  • 3 Beds
  • 2 Baths
  • Seaplace SubDv.
  • 34228 Zip Code
5442 Gulf Of Mexico Dr, Longboat Key image
5442 Gulf Of Mexico Dr, Longboat Key $13,850,000

Stunning contemporary spectacular bayfront estate on Longboat Key with unrivalled panoramic penthouse like views of Sarasota Bay, Anna Maria, and even downtown Sarasota....

  • 5 Beds
  • 5 Baths
  • Cedar Woodlands SubDv.
  • 34228 Zip Code
701 Penfield Street, Longboat Key image
701 Penfield Street, Longboat Key $1,499,000 ▼

Perfectly situated in the coveted Sleepy Lagoon north Longboat Key community, you will find this hidden waterfront gem with loads of curb appeal located on a deep water c...

  • 2 Beds
  • 2 Baths
  • Sleepy Lagoon SubDv.
  • 34228 Zip Code
3320 Gulf Of Mexico Drive Unit 208-C, Longboat Key image
3320 Gulf Of Mexico Drive Unit 208-C, Longboat Key — Bldg C $714,900

Beautiful Longboat Key with its famous beaches and relaxed lifestyle awaits you ! This 2nd Floor corner end unit offers the clear beautiful views of water. Enjoy this fr...

  • 2 Beds
  • 2 Baths
  • Longboat Arms SubDv.
  • 34228 Zip Code
2151 Gulf Of Mexico Drive Unit 4, Longboat Key image
2151 Gulf Of Mexico Drive Unit 4, Longboat Key — 2 $4,200,000 ▼

Year-round blue skies, turquoise waters and spectacular sunsets are the main attractions at this beachfront condominium on Longboat Key. Tucked away on nearly six acres o...

  • 3 Beds
  • 3.5 Baths
  • En Provence SubDv.
  • 34228 Zip Code
741 Saint Judes Drive S Unit 1, Longboat Key image
741 Saint Judes Drive S Unit 1, Longboat Key — 747 $799,900 ▲

This Pet Friendly Villa on Longboat Key’s Sarasota Bay features sweeping views to the south and east for stunning sunrises. Sparkling Quartz counters. Upgrades include po...

  • 2 Beds
  • 2 Baths
  • Saint Judes Apts Unit 3 Condo Association Inc SubDv.
  • 34228 Zip Code
537 Spinnaker Lane, Longboat Key image
537 Spinnaker Lane, Longboat Key $2,375,000 ▼

Your Boating to Beach paradise house awaits you in one of the most sought-after neighborhoods "Country Club Shores" on Longboat Key. This charming home has a smart 3 bedr...

  • 3 Beds
  • 3 Baths
  • Country Club Shores SubDv.
  • 34228 Zip Code
3320 Gulf Of Mexico Drive Unit 303-C, Longboat Key image
3320 Gulf Of Mexico Drive Unit 303-C, Longboat Key — N/A $625,000

Beautifully remodeled condo in a prime location on pristine shores of Longboat Key, Florida's exclusive Gulf Coast Island. Beautifully finished & furnished, move-in ready...

  • 2 Beds
  • 2 Baths
  • Longboat Arms SubDv.
  • 34228 Zip Code
3806 Gulf Of Mexico Drive Unit C404, Longboat Key image
3806 Gulf Of Mexico Drive Unit C404, Longboat Key — C/3806 $895,000

Sitting on top of the world in Paradise awaits you here. Wonderful water views are available from every room of this well-appointed penthouse which has two garden rooftop...

  • 2 Beds
  • 2 Baths
  • Beach Harbor Club SubDv.
  • 34228 Zip Code
816 Jungle Queen Way, Longboat Key image
816 Jungle Queen Way, Longboat Key $1,695,000

Fourth home in from Sarasota Bay, this turnkey furnished residence on the Longboat Key’s north end is move-in ready. You will love the convenience of moving right in to e...

  • 3 Beds
  • 2 Baths
  • Longboat Key SubDv.
  • 34228 Zip Code
2333 Gulf Of Mexico Drive Unit 1C2, Longboat Key image
2333 Gulf Of Mexico Drive Unit 1C2, Longboat Key — Building 1 $4,895,000 ▼

With the splendor of stunning Gulf of Mexico views, the amenities of a world-class resort, and the space and comfort that lives like a sprawling, luxury single-family hom...

  • 4 Beds
  • 4.5 Baths
  • Vizcaya At Longboat Key SubDv.
  • 34228 Zip Code
846 Evergreen Way, Longboat Key image
846 Evergreen Way, Longboat Key — N/A $619,900 ▼

New price, new opportunity! The Longboat Key lifestyle can be yours. First time on the market in over 27 Years. Well-loved and cared for Townhome in Cedars East Fitness ...

  • 2 Beds
  • 2.5 Baths
  • Cedars East SubDv.
  • 34228 Zip Code
2039 Gulf Of Mexico Drive Unit G3-103, Longboat Key image
2039 Gulf Of Mexico Drive Unit G3-103, Longboat Key — G3 $499,900

This 2-bedroom & 1.5 bath condo is located G3 building ground floor unit 103. The unit is being offered as Turnkey furnished. AC 2022 Hot water Heater 2020. This condo wo...

  • 2 Beds
  • 1.5 Baths
  • Seaplace SubDv.
  • 34228 Zip Code
2800 Harbourside Drive Unit E-10, Longboat Key image
2800 Harbourside Drive Unit E-10, Longboat Key $263,000

60' x 20' boat slip at The Longboat Key Club Moorings Marina. As one of the finest protected deep water yacht marinas on the West Coast of Florida, only a select few ha...

  • Longboat Key Moorings SubDv.
  • 34228 Zip Code
3060 Grand Bay Boulevard Unit 1101, Longboat Key image
3060 Grand Bay Boulevard Unit 1101, Longboat Key — 3060 $4,999,999 ▼

One or more photo(s) has been virtually staged. RARE OPPORTUNITY Top of The World PENTHOUSE. Boasting an astounding 5,300 square feet of wraparound terrace space and floo...

  • 4 Beds
  • 5.5 Baths
  • Grand Bay SubDv.
  • 34228 Zip Code
525 Channel Lane, Longboat Key image
525 Channel Lane, Longboat Key $925,000

Make this south Longboat Key Bungalow home yours and be located close to St. Armands Circle (just 2 miles away) as well as all Sarasota has to offer including Marina Jac...

  • 2 Beds
  • 2 Baths
  • New Pass Shores SubDv.
  • 34228 Zip Code
2004 Harbourside Drive Unit 1701, Longboat Key image
2004 Harbourside Drive Unit 1701, Longboat Key — Fairway Bay 2 $985,000 ▼

A significant reduction in the price makes this property the least expensive townhouse in all of Bay Isles.***NEW PRICE $998,000*** Beautiful totally updated end unit Fa...

  • 2 Beds
  • 2 Baths
  • Fairway Bay SubDv.
  • 34228 Zip Code
540 Harbor Cove Circle, Longboat Key image
540 Harbor Cove Circle, Longboat Key $3,600,000

Build your dream home on this oversized waterfront lot in the exclusive gated neighborhood of Bay Isles Harbor Section! This neighborhood definitely has the boater in mi...

  • Bay Isles SubDv.
  • 34228 Zip Code
500 Harbor Cove Circle, Longboat Key image
500 Harbor Cove Circle, Longboat Key $7,000,000

Pre-Construction. To be built. Located in the exclusive Harbor Section of Bay Isles right across the street from the new St. Regis. The new tropical modern residence will...

  • 5 Beds
  • 5.5 Baths
  • Bay Isles SubDv.
  • 34228 Zip Code
2089 Gulf Of Mexico Drive Unit 204, Longboat Key image
2089 Gulf Of Mexico Drive Unit 204, Longboat Key — 2089 $1,999,000

Your piece of paradise has just arrived on the market on beautiful Longboat Key! This exquisitely renovated and redesigned residence has an open kitchen and living area d...

  • 2 Beds
  • 2.5 Baths
  • Seaplace SubDv.
  • 34228 Zip Code
435 L Ambiance Drive Unit G601, Longboat Key image
435 L Ambiance Drive Unit G601, Longboat Key — 000 $6,880,000

Ready for instant enjoyment and to create memories for a lifetime. It’s all about the view and unparalleled location! Choice Southwest Corner residence @ 435 L’Ambiance...

  • 3 Beds
  • 3 Baths
  • L'Ambiance SubDv.
  • 34228 Zip Code
641 Fox Street, Longboat Key image
641 Fox Street, Longboat Key $550,000

Build your dream home in "The Village" on Longboat Key. 50-by-105, vacant land on the corner of Fox Street and Poinsettia Avenue. The island lifestyle awaits you, with ac...

  • Long Beach SubDv.
  • 34228 Zip Code
656 Tarawitt Drive, Longboat Key image
656 Tarawitt Drive, Longboat Key $1,300,000

Act fast, this is the only open lot in longboat key with direct water access under 3.6 million dollars! Bring your boat and dock it next to your custom dream home! This...

  • Longboat Key SubDv.
  • 34228 Zip Code
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