105 21ST AVENUE, St Pete Beach, FL 33706

• 5 beds |
• 4 baths |
• 2,765 sqft

Property Description

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 Status:

Active

Date Added:

June 26, 2026

Data Last Updated:

July 26, 2026 at 6:23PM

Listing Office:

EXP REALTY : 727-592-2286

Listing Agent:

Brandon Tecklenburg : 727-265-6269

MLS ID:

TB8520827

Interior

• General: Ceiling Fans(s)Stone Counters
• Rooms: Bonus Room
• Appliances: Disposal
• Laundry: Inside
• Flooring: Luxury VinylTile
• A/C: Central Air
• Heating: Central
• Fireplace: Wood BurningFireplace

Exterior

• General: BalconyFrench DoorsOutdoor ShowerRain Gutters
• Other Structures: Guest HouseEnclosedPatioCovered
• Parking: Garage Faces Rear

Construction

• Roofing: Metal
• Windows: Blinds
• General: FrameWood SidingTwoPillar/Post/Pier

Location

• Road/Access: Asphalt
• Originating MLS: Stellar MLS
• County: Pinellas

Lot

• Zoning: PHILLIPS DIVISION REV MAP BLK JLOT 6818-32-16-68634-010-0680
• Fencing: FencedVinyl

Utilities

• Utilities: Cable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple