Location: Phillips Div Rev Map, St Pete Beach
Do Not Show Listings
105 21ST AVE, ST PETE BEACH, FL 33706
$1,500,00011 Days on yellowkey MLS ID: TB8520827
INCREASED by $100,000 (7.1%) on 06/30/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2765 Built: 1934 Tax: $14,667 (2025)Community: Phillips Div Rev MapSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,667
Elementary School: Azalea Elementary-PN
High School: Boca Ciega High-PN
Tax Year: 2025
Middle School: Bay Point Middle-PN
Remarks: 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.
Listing is courtesy of: EXP REALTY (727-592-2286)
Listing Agent: Brandon Tecklenburg (727-265-6269)
1801 PASS A GRILLE WAY, ST PETE BEACH, FL 33706
$10,000,000120 Days on yellowkey MLS ID: TB8481141
Bed: 5 Bath: 5.5 Gar: 7 Liv Area Sq Ft: 5497 Built: 2019 Tax: $28,379 (2025)Community: Phillips Div Rev MapSpa: YesSingle Family
Taxes:$28,379
Remarks: *Interior and construction photos are available upon request, after a proof of funds or pre approval letter* One of the best, strongest homes ever constructed in Pass A Grille Beach. This waterfront fortress sits on an oversized lot with amazing views of the intra-coastal waterway, perfect for sunrises and sunsets. This entire home is a custom masterpiece that was thoughtfully built. It is a wonderful blend of modern clean lines and coastal warmth. The location could not be more perfect. You can walk 600 ft to the beautiful sands of Pass A Grille Beach but also enjoy a private waterfront backyard, facing East for shaded afternoons complete with heated saltwater pool and spa. The backyard features a PGA putting green and new turf throughout the property. It is the ONLY home in Pass A Grille in the No Wake Zone that has a wide open water view! For boating, no bridges to the Gulf of America, straight shot south, less than a mile away. You are minutes from the interstate if you wish to travel, or you can walk to local shops and restaurants. With a south side street to access your driveway, you have plenty of private parking for guests. This property has many features that are unique to the area, that may not be able to be duplicated ever again.
Listing is courtesy of: ROCK REAL ESTATE (813-951-0453)
Listing Agent: Abigail Kotchman (813-951-0453)
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