105 21st Avenue

The 1934 Historic Pineapple House is on the market and should be on your radar! This rare 92-year-old coastal compound in the heart of Pass-a-Grille is a one-of-a-kind property offering the perfect blend of historic island charm and modern updates with a beautifully renovated 3-bedroom, 2-bath main residence plus a second-story 2-bedroom, 2-bath guest house, separated by a large solid wood and insulated conjoining door that offers the new buyer the option of having a 5-bedroom, 4-bath with two kitchens and two indoor laundry locations with endless possibilities for extended family, guests, or additional income potential. No Pass-a-Grille parking problem here, as the home has a side-by-side two-vehicle parking garage and a two-vehicle carport. Rich in character, the main home features soaring tongue-and-groove ceilings, exposed wood beams, original hardwood floors, and abundant natural light throughout. The updated kitchen offers shaker cabinetry, stone countertops, and stainless steel appliances and leads into the living spaces designed for relaxed coastal living. The spacious second-floor primary suite is timeless and serves as a private retreat with a spa-inspired bath and connecting bonus room perfect for a home office or coffee/wine bar. The additional guest bedrooms provide comfort for family and guests. The attached guest house has been thoughtfully updated, maintaining its timeless coastal character, offering a full kitchen, spacious living area, two bedrooms, and two full baths. The exterior is private, and a covered entertainment area boasts a large kitchen counter, flat screen TV, and power and gas line to add an outdoor refrigerator and gas grill, perfect for gathering after a day at the beach. Located just steps from the sugar-sand beaches of Pass-a-Grille, boutique shopping, waterfront dining, marinas, and historic 8th Avenue, this exceptional property offers a rare opportunity to own one of the area’s classic island homes. Whether you’re searching for a primary residence, a vacation retreat, or an investment with exceptional flexibility, this unique coastal compound truly has it all. The 2/2 guest quarters are currently rented for $3000 a month, plus the renter pays utilities. The main house rents monthly between $6,000 and $15,000 a month depending on the season. 24-hour notice for showings as the property is currently occupied. Currently July, August, December 2026, and January and March-April 14, 2027, are rented.