Longboat Key, FL Homes for Sale under $500,000

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  /13

  $265,000

  26OO Harbourside Dr Unit O-06, Longboat Key, FL 34228

  A great view of the bay and city skyline along with easy boat access! This 50 x 20 foot slip at Longboat Key Club Moorings is located on the south side of O-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

  Jennifer Wilson LBRE LLC

  26OO Harbourside Dr Unit O-06, Longboat Key, FL 34228
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  /58

  $475,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  3240 Gulf of Mexico Dr Unit B104, Longboat Key, FL 34228

  Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from

  Laura Rode KW COASTAL LIVING III

  3240 Gulf of Mexico Dr Unit B104, Longboat Key, FL 34228
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  /17

  $265,000

  $35K PRICE DROP

  2600 Harbourside Dr Unit Q-08, Longboat Key, FL 34228

  A fantastic view of the city skyline from the 48 x 21 foot slip at Longboat Key Club Moorings! 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, shopping (close to Publix, CVS, and

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit Q-08, Longboat Key, FL 34228
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  /20

  $500,000

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

  A 100 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, extra wide finger pier, and deep water. Huge turning radius, with easy access slip with the views to match 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,

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit B-13, Longboat Key, FL 34228
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  /24

  $348,000

  $21K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 657 Sq Ft

  2850 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Own your slice of paradise on Longboat Key with this charming 1-bedroom, 1-bath condo located at 2850 Gulf of Mexico Dr Unit 5. Just directly across from public beach access, this 657 sq ft ground-floor unit is perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  2850 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
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  /72

  $435,000

  • 2 Beds
  • 2 Baths
  • 1,326 Sq Ft

  554 Spanish Dr S, Longboat Key, FL 34228

  Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and

  Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  554 Spanish Dr S, Longboat Key, FL 34228
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  /53

  $349,900

  $120K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 883 Sq Ft

  600 Sutton Place Unit 101, Longboat Key, FL 34228

  Waterfront condo with Sarasota Bay views!Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, this exceptional community offers the ultimate coastal lifestyle in an unbeatable location. Current owners have never had water intrusion from any hurricanes.This spacious ground-floor corner residence features an

  Jill Baldwin MARINA PARK REALTY LLC

  600 Sutton Place Unit 101, Longboat Key, FL 34228
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  /21

  $250,000

  $19K PRICE DROP

  2800 Harbourside Dr Unit M-03, Longboat Key, FL 34228

  45 x 20 Boat Slip on M-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline, close to parking for easy access. LBK Club membership is optional. 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, Marina village that includes

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit M-03, Longboat Key, FL 34228
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  /23

  $339,000

  2800 Harbourside Dr Unit F-06, Longboat Key, FL 34228

  Slip F-06 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 70 X 26, and a usable beam of 23 feet and a 32 FT long finger pier. This location provides close proximity to parking with a view of the west side of the marina and golf courses. The Longboat Key Club Moorings Marina is a World Class deep

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit F-06, Longboat Key, FL 34228
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  /20

  $300,000

  2800 Harbourside Dr Unit E-12, Longboat Key, FL 34228

  Spacious E-dock! Slip E-12, a 60 ft x 21 ft. slip in the marina. Plenty of deep water and cool breezes. LBKC Membership is required. A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit E-12, Longboat Key, FL 34228
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  /59

  $479,000

  $44K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 882 Sq Ft

  779 Saint Judes Dr N, Longboat Key, FL 34228

  PRICED TO SELL ! Coastal Elegance Meets Effortless Island Living in Longboat KeyExperience the ultimate Gulf Coast lifestyle in this beautifully maintained 2-bedroom, 1.5-bath canal-front residence, perfectly positioned within one of Longboat Key's most desirable waterfront communities.Whether you're searching for a full-time sanctuary or a refined seasonal retreat, this exceptional

  Alessandro Rosa BROKERS REAL ESTATE GROUP INC

  779 Saint Judes Dr N, Longboat Key, FL 34228
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  /40

  $349,000

  $47K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  541 Spanish Dr N Unit 5, Longboat Key, FL 34228

  1 Block from private beach, completely remodeled 1100 sq ft modernized condo with open concept and lot of windows. Custom kitchen, completely gutted and new insulation and drywall. Custom glass-walls, 3 A/C zones. Villa is in 55 plus community with private beach and marina, clubhouse, shuffle board, in peaceful LongBoat Key.

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  541 Spanish Dr N Unit 5, Longboat Key, FL 34228
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  /19

  $425,000

  2600 Harbourside Dr Unit B-06, Longboat Key, FL 34228

  A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit B-06, Longboat Key, FL 34228
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  /21

  $270,000

  $5K PRICE DROP

  2600 Harbourside Dr Unit H-09, Longboat Key, FL 34228

  Many boaters feel H-dock is the best dock in the marina; convenient to the showers, and the marina village and office. Slip is at the seawall with easy in/out access. A 55 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit H-09, Longboat Key, FL 34228
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  /20

  $330,000

  2800 Harbourside Dr Unit M-10, Longboat Key, FL 34228

  A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit M-10, Longboat Key, FL 34228
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  /15

  $300,000

  2600 Harbourside Dr Unit I-09, Longboat Key, FL 34228

  The middle pier, right in front at Longboat Key Club! I-09, a 60 ft x 21 ft. slip in the marina. This is the only north-south pier in the marina; plenty of deep water and cool breezes. 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

  2600 Harbourside Dr Unit I-09, Longboat Key, FL 34228
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  /20

  $270,000

  $5K PRICE DROP

  • Land
  • 1,100 Sq Ft
  • $10,692,000 per Acre

  2600 Harbourside Dr Unit H-10, Longboat Key, FL 34228

  One of two slips for sale side by side...right up front. Perfect for your fleet! A 55 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit H-10, Longboat Key, FL 34228
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  /20

  $350,000

  • 1,155 Sq Ft

  2600 Harbourside Dr Unit C-04, Longboat Key, FL 34228

  Unique with a 42 ft long finger pier and is nicely protected on the west bank at Longboat Key Club Moorings from this 55 ft x 21 ft. slip in the marina. Enjoy all the amenities of the private Longboat Key Club as a Club Member. 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

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit C-04, Longboat Key, FL 34228
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  /77

  $389,000

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft

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

  Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seaoats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized

  Len Scavron LEN SCAVRON

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
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  /19

  $300,000

  2600 Harbourside Dr Unit H-05, Longboat Key, FL 34228

  The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Nicely manicured lawn fronts the area at the slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much as a resort as any other neighborhood on the island, thanks to individual slip ownership, a

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit H-05, Longboat Key, FL 34228
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  /35

  $350,000

  • 2 Beds
  • 2 Baths
  • 1,429 Sq Ft

  597 Spanish Dr N Unit 12, Longboat Key, FL 34228

  Enjoy the Florida lifestyle in this beautifully renovated 2-bedroom + den, 2-bath villa in the highly desirable Spanish Main Yacht Club on Longboat Key. Offering 1,429 sq. ft. of move-in-ready living space, this home features ceramic tile flooring throughout, an open-concept living and dining area, and a bright Florida room ideal for relaxing or entertaining. The den includes a closet, making it

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  597 Spanish Dr N Unit 12, Longboat Key, FL 34228
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  /17

  $425,000

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228

  Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and

  Brooke Moran DALTON WADE INC

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228
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  /17

  $275,000

  2600 Harbourside Dr Unit H-04, Longboat Key, FL 34228

  A favorite dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Easy access on and off the water to this H-dock slip. 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

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit H-04, Longboat Key, FL 34228
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  /43

  $475,000

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228

  Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer

  Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

  6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228
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  /18

  $300,000

  $25K PRICE DROP

  2800 Harbourside Dr Unit E-16, Longboat Key, FL 34228

  A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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

  Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit E-16, Longboat Key, FL 34228

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