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Longboat Key, FL Homes for Sale in a Senior Community

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  • /59

    $2,100,000

    • 2 Beds
    • 2 Baths
    • 1,485 Sq Ft

    2295 Gulf of Mexico Dr Unit 83S, Longboat Key, FL 34228

    Imagine waking up each morning to the gentle sound of waves and a breathtaking view of the Gulf from every room in your home. This stunning 2-bedroom, 2-bathroom residence offers just that, with a 35-foot lanai that perfectly frames the spectacular scenery. Recently remodeled, this home embodies luxury, comfort, and style. The interior of this residence is nothing short of remarkable. Light-toned

    Agent Photo

    Peter Ingrasselino

    DEAL HOUSE REALTY LLC

    (941) 451-5590

    2295 Gulf of Mexico Dr Unit 83S, Longboat Key, FL 34228
  • /17

    $109,000

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    85 Twin Shores Blvd, Longboat Key, FL 34228

    Location, location location! This flood impacted mobile home is being sold AS-IS, and is your opportunity to own a slice of paradise with PRIVATE BEACH ACCESS, MARINA ACCESS, community saltwater pool and more. Ready to enjoy million dollar sunsets without the typical million dollar Longboat Key price tag? Twin Shores is a secret gem of Longboat Key- the community spans from the Gulf to the Bay.

    Erica Smentowski KELLER WILLIAMS ON THE WATER S

    85 Twin Shores Blvd, Longboat Key, FL 34228
  • /34

    $385,000

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

    564 Spanish Dr N, Longboat Key, FL 34228

    Fantastic value! Fabulous lake view. This is an opportunity to purchase in this old Florida-style community of Spanish Main Yacht Club. A blank canvas ready for you. Customize this villa to reflect your style, taste and needs. The lovely neighborhood of Spanish Main welcomes you home with villa living at its best. This home has a large dining/great room combo that opens onto an expansive lanai

    Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

    564 Spanish Dr N, Longboat Key, FL 34228
  • /45

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft

    655 Spanish Way, Longboat Key, FL 34228

    Amazing views! This villa is positioned to provide gorgeous, elongated views of the Spanish Main community lake. The vistas from almost every room are spectacular. Have your morning coffee, evening beverages with gorgeous sunsets or simply relax as you enjoy shimmering waters. The lake is home to turtles, an abundance of fish, and beautiful Florida birds and you watch it all from your new home.

    Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

    655 Spanish Way, Longboat Key, FL 34228
  • /9

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,427 Sq Ft

    594 Spanish Dr S, Longboat Key, FL 34228

    Welcome to this 2-bedroom, 2-bath villa located in the highly desirable 55+ community of Spanish Main Yacht Club on the north end of Longboat Key. Offering the perfect blend of privacy, potential, and location, this villa is ideal as a full-time residence, seasonal getaway, or investment opportunity. Enjoy exclusive access to the community’s private marina and secluded beach, just a short stroll

    Amber Lynch COMPASS FLORIDA LLC

    594 Spanish Dr S, Longboat Key, FL 34228
  • /27

    $359,000

    • 2 Beds
    • 2 Baths
    • 1,087 Sq Ft

    669 Spanish Dr N Unit 21, Longboat Key, FL 34228

    Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. This 2-bedroom, 2-bath villa-style condo offers 1700 SqFt of interior living space, 1087 of it under air, with endless potential to make it your dream home.This stand-alone condo has undergone FEMA-approved storm mitigation, including new electrical

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    669 Spanish Dr N Unit 21, Longboat Key, FL 34228
  • /16

    $399,500

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft

    730 Spanish Dr S Unit 99, Longboat Key, FL 34228

    Now is the time to buy this beautiful home in Spanish Main Yacht Club at an exceptionally low price. This 2 bedroom, 2 bathroom villa is being renovated to code after Hurricane Helene and the attractive price reflects that it will not be ready to inhabit until estimated mid-summer 2025. Once you move in, you will enjoy Spanish Main's low-maintenance Longboat Key lifestyle with many restaurants

    Bill Anderson MICHAEL SAUNDERS & COMPANY

    730 Spanish Dr S Unit 99, Longboat Key, FL 34228
  • /17

    $90,000

    • 2 Beds
    • 2 Baths
    • 852 Sq Ft

    73 Twin Shores Blvd, Longboat Key, FL 34228

    NEW PRICE...INCREDIBLE VALUE!! Here's your chance to own a slice of paradise at an unbeatable price. Listed well below land value due to damage from Hurricane Helene, this property offers amazing potential in a highly sought-after 55+ Beach-to-Bay community. Perfect for investors, snowbirds, or anyone ready to create their dream coastal retreat. Whether you bring in a new manufactured home or

    Mary Moore WAGNER REALTY

    73 Twin Shores Blvd, Longboat Key, FL 34228
  • /24

    $250,000

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    3710 Gulf of Mexico Dr Unit A20, Longboat Key, FL 34228

    WELCOME TO PARADISE! Gulfshore of Longboat Key has it all - private, pristine sand beach, combined with the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large heated community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit A20, Longboat Key, FL 34228
  • /32

    $385,000

    • 2 Beds
    • 1 Bath
    • 680 Sq Ft

    3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228

    BEAUTIFULLY REMODLED: This home is the epitome of simple elegance. It has been remodeled to create a home that is open and full of light. It features a large Living Room with a wall-mounted TV and a fireplace; a kitchen that has all new cabinets and granite counter tops; two Bedrooms and a full Bath with a step-in shower. Grayhawk windows were installed three years ago. In addition, there is

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228
  • /31

    $115,000

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    96 Main Street Dr, Longboat Key, FL 34228

    Location! Location! And excellent value. Live in paradise on Longboat Key with the Bay and Marina on one side and the beach/gulf on the other side. Deeded beach access and private marina with 16 boat slips. This property is being sold as-is and is offered well below its taxable land value. I have done the homework for you to add a new modular home, elevated to approximately 9 feet with potential

    Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

    96 Main Street Dr, Longboat Key, FL 34228
  • /57

    $1,549,900

    • 3 Beds
    • 3 Baths
    • 2,051 Sq Ft

    1465 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

    SPECIAL HOLIDAY PRICING. Indulge in the ultimate coastal escape with this rare 3-bedroom, 3-full-bath, turnkey furnished Gulf-front residence—perfectly positioned next door to the St. Regis on Longboat Key. Wake up to sweeping Gulf views, stroll along the pristine shoreline, and relax in a beautifully maintained, amenity-rich environment designed for effortless beach living. Located within the

    Lori Carey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1465 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
  • /25

    $159,000

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    3710 Gulf of Mexico Dr Unit D19, Longboat Key, FL 34228

    FANTASTIC OPPORTUNITY to own a home in a beach-to-bay community. Gulfshore of Longboat Key has it all -- private, pristine sand beach, on the Gulf of Mexico, a marina (needs to be repaired) on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit D19, Longboat Key, FL 34228
  • /30

    $199,900

    • 1 Bed
    • 1 Bath
    • 482 Sq Ft

    31 Twin Shores Blvd, Longboat Key, FL 34228

    HUGE PRICE REDUCTION: Twin Shores Beach and Marina, on Longboat Key, is a unique community. It extends from the Gulf of Mexico to Sarasota Bay. It features a private, pristine sand beach on the Gulf of Mexico with its clear turquoise waters and a marina on Sarasota Bay. Facilities include a clubhouse, a well-maintained campus and very reasonable HOA fees. Truly, Twin Shores is a remnant of Old

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    31 Twin Shores Blvd, Longboat Key, FL 34228
  • /12

    $1,000,000

    • 2 Beds
    • 2 Baths
    • 1,399 Sq Ft

    957 Spanish Dr N, Longboat Key, FL 34228

    LONGBOAT KEY WATERFRONT CONDO. UNOBSTRUCTED VIEW OF THE BAY. PEACEFUL LOCATION. BEAUTIFUL MARBLE FLOORS. A STAND ALONE CONDO UNATTACHED. LOCATED IN THE SOUGHT AFTER SPANISH MAIN YACHT CLUB ASSOCIATION. ALL THE AMENITIES INCLUDING DOCKAGE, POOL, CLUBHOUSE AND MUCH MORE.

    Daniel Novak PRIME TIME REAL ESTATE INC

    957 Spanish Dr N, Longboat Key, FL 34228
  • /67

    $1,540,000

    • 2 Beds
    • 2 Baths
    • 1,458 Sq Ft

    603 Longboat Club Rd Unit 602N, Longboat Key, FL 34228

    Experience the ultimate in luxury living with this stunning 2-bedroom, 2-bathroom condo in the most prestigious area of Longboat Key Club. Enjoy the best of both worlds with breathtaking views of the Gulf on one side and Sarasota Bay and the LBK Golf Course on the other, all from your dual-sided balcony.This fully furnished, turnkey condo is move-in ready or perfect for generating rental

    Tina Napoli COLDWELL BANKER REALTY

    603 Longboat Club Rd Unit 602N, Longboat Key, FL 34228
  • /18

    $199,999

    • 2 Beds
    • 1 Bath
    • 680 Sq Ft

    3710 Gulf of Mexico Dr Unit E3, Longboat Key, FL 34228

    JUST ELEVATED! Gulfshore of Longboat Key, Inc. offers it all. It extends from the Gulf of Mexico to Sarasota Bay. It has approximately 450- 500 feet of frontage on the Gulf, a marina on Sarasota Bay, a large heated community pool, fabulous club house with a commercial kitchen and much more. It is one of the best kept secrets on Longboat. Truly, Gulfshore is a remnant of Old Florida that is

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit E3, Longboat Key, FL 34228

Home Trends in Longboat Key, FL

Housing Trends

Median Sale Price
$2,000,000
Median Single Family Sale Price
$2,000,000
Median 2 Bedroom Sale Price
$1,620,000
Median 1 Bedroom Sale Price
$1,000,000
Average Price Per Sq Ft
$1,138
Number of Homes for Sale
24
Last 12 months Home Sales
166
Months of Supply
1.70
Median List Price
$1,725,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
488%
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