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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, 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 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, 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 private and a covered entertainment area boasts a large kitchen counter, flat screen tv, and power and gas line to add outdoor refrigerator and 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, vacation retreat, or an investment with exceptional flexibility, this unique coastal compound truly has it all. The 2/2 guest quarters is currently rented for $3000 a month plus renter pays utilities. Main house rents monthly between $6000 to $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, March-April 14, 2027 are rented.

5 Beds ⋅ 4 Baths ⋅ Phillips Div Rev Map SubDv. ⋅ 33706 Zip Code

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, 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 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, 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 private and a covered entertainment area boasts a large kitchen counter, flat screen tv, and power and gas line to add outdoor refrigerator and 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, vacation retreat, or an investment with exceptional flexibility, this unique coastal compound truly has it all. The 2/2 guest quarters is currently rented for $3000 a month plus renter pays utilities. Main house rents monthly between $6000 to $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, March-April 14, 2027 are rented.

105 21st Avenue, St Pete Beach

$875,000

This exceptional building lot places you just three homes from the powder-soft white sands and shimmering Gulf waters — a location where the rhythm of the tide becomes part of everyday life. Currently situated on the property is a well-maintained duplex along with a separate outbuilding, offering immediate income potential while you design and plan your custom coastal retreat. Whether you choose to continue generating revenue or move forward with new construction right away, the flexibility here is rare and valuable. Imagine waking to salt-tinged breezes, strolling barefoot to the shoreline for morning walks, and ending each day with spectacular Gulf sunsets just steps from your door. Nestled on a desirable, quiet block yet moments from the charm of local cafés, boutiques, and waterfront dining, this property represents more than a homesite — it’s a chance to create a legacy residence in one of Florida’s most treasured beach communities. Build boldly. Live beautifully. Embrace the lifestyle only Pass-a-Grille can offer. Note: Directly across the street, the seller also owns a one-bedroom timeshare at Camelot By The Sea, which includes year-round access to the resort’s pool, hot tub, sauna, shuffleboard courts, and outdoor grilling area. If of interest, the seller may consider transferring the timeshare to a buyer by separate agreement, offering convenient guest overflow accommodations and resort-style amenities just steps away.

4 Beds ⋅ 2 Baths ⋅ Phillips Div Rev Map SubDv. ⋅ 33706 Zip Code

This exceptional building lot places you just three homes from the powder-soft white sands and shimmering Gulf waters — a location where the rhythm of the tide becomes part of everyday life. Currently situated on the property is a well-maintained duplex along with a separate outbuilding, offering immediate income potential while you design and plan your custom coastal retreat. Whether you choose to continue generating revenue or move forward with new construction right away, the flexibility here is rare and valuable. Imagine waking to salt-tinged breezes, strolling barefoot to the shoreline for morning walks, and ending each day with spectacular Gulf sunsets just steps from your door. Nestled on a desirable, quiet block yet moments from the charm of local cafés, boutiques, and waterfront dining, this property represents more than a homesite — it’s a chance to create a legacy residence in one of Florida’s most treasured beach communities. Build boldly. Live beautifully. Embrace the lifestyle only Pass-a-Grille can offer. Note: Directly across the street, the seller also owns a one-bedroom timeshare at Camelot By The Sea, which includes year-round access to the resort’s pool, hot tub, sauna, shuffleboard courts, and outdoor grilling area. If of interest, the seller may consider transferring the timeshare to a buyer by separate agreement, offering convenient guest overflow accommodations and resort-style amenities just steps away.

104 18th Avenue, St Pete Beach

$875,000

Remarkable opportunity on one of the most sought-after blocks in Pass-a-Grille. This exceptional building lot places you just three homes from the powder-soft white sands and shimmering Gulf waters — a location where the rhythm of the tide becomes part of everyday life. Currently situated on the property is a maintained and occupied duplex along with a separate outbuilding, offering immediate income potential while you design and plan your custom coastal retreat. Whether you choose to continue generating revenue or move forward with new construction right away, the flexibility here is rare and valuable. Imagine waking to salt-tinged breezes, strolling barefoot to the shoreline for morning walks, and ending each day with spectacular Gulf sunsets just steps from your door. Nestled on a desirable, quiet block yet moments from the charm of local cafés, boutiques, and waterfront dining, this property represents more than a homesite — it’s a chance to create a legacy residence in one of Florida’s most treasured beach communities. Build boldly. Live beautifully. Embrace the lifestyle only Pass-a-Grille can offer.

Phillips Div Rev Map SubDv. ⋅ 33706 Zip Code

Remarkable opportunity on one of the most sought-after blocks in Pass-a-Grille. This exceptional building lot places you just three homes from the powder-soft white sands and shimmering Gulf waters — a location where the rhythm of the tide becomes part of everyday life. Currently situated on the property is a maintained and occupied duplex along with a separate outbuilding, offering immediate income potential while you design and plan your custom coastal retreat. Whether you choose to continue generating revenue or move forward with new construction right away, the flexibility here is rare and valuable. Imagine waking to salt-tinged breezes, strolling barefoot to the shoreline for morning walks, and ending each day with spectacular Gulf sunsets just steps from your door. Nestled on a desirable, quiet block yet moments from the charm of local cafés, boutiques, and waterfront dining, this property represents more than a homesite — it’s a chance to create a legacy residence in one of Florida’s most treasured beach communities. Build boldly. Live beautifully. Embrace the lifestyle only Pass-a-Grille can offer.

104 18th Avenue, St Pete Beach