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105 21st Avenue

Saint Petersburg Beach, FL 33706
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Bed 5

Bed

Bath 4

Bath

SqFt2,765

Sqft

Acres0.11

Acre(Lot)

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 t ongue-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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,400,000

AD Id : 86499471

MLS Id : MFRTB8520827

Beds : 5

Lot Size : 0.11 Acre

Living Area Size : 2,765

Year Built : 1934

Garage : 2

County : Pinellas

Subdivision: Phillips Div Rev Map

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Map

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Feature Features

  • Bedroom Information

    Total Bedroom: 5

    Bathroom Information

    Total Baths: 4 Full Baths: 4

    Interior Features

    Ceiling Fans(s), Stone Counters Roof: Metal Appliances: Disposal Laundry Features: Inside

    Roofing Information

    Metal
  • Flooring Information

    Flooring: Luxury Vinyl, Tile Construction Materials: Frame, Wood Siding
  • Heating & Cooling

    Heating: Central Cooling: Central Air WaterSource: Public

  • Building Information

    Year Built: 1934
  • Exterior Features

    Balcony, French Doors, Outdoor Shower, Rain Gutters Construction Materials: Frame, Wood Siding Foundation Details: Pillar/Post/Pier

  • Lot Information

    Lot Dimensions: 50x100 Lot Description: Historic District, Near Golf Course, Near Marina, Near Public Transit, Sidewalk Lot Square Feet: 5001 Lot Acres: 0.11 Lot Size (SqMt): 465

    Property Information

    Property Type: Residential Sub Type: Single Family Residence

  • Listing Price Information

    Original List Price:$1400000

  • Tax Information

    Tax Block: J Tax Book Number: 3-38 Tax Lot: 68 Tax Legal Description: PHILLIPS DIVISION REV MAP BLK J, LOT 68 Annual Tax: $14666.84 Tax Year: 2025 Parcel Number: 18-32-16-68634-010-0680

  • Parking Information

    Garage Faces Rear

    Garage Information

    Has Garage: Yes Garage Space: 2 Garage Dimensions: 26x17

  • School Information

    Elementary School: Azalea Elementary-PN Junior High School: Bay Point Middle-PN Senior High School: Boca Ciega High-PN
  • Utility Information

    Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected Sewer: Public Sewer Water Source: Public
  • Location Information

    Subdivision: PHILLIPS DIV REV MAP City: ST PETE BEACH Direction: From Gulf Blvd heading south, GUlf Blvd turns into Pass a Grille way. At the stop sign, turn right onto 21st Ave property will be on the right
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ByOwner last updated this listing 06/27/2026 @ 18:20

MLS: MFRMLS #TB8520827 LISTED BY: Brandon Tecklenburg, EXP REALTY 727-592-2286 SOURCE: MFRMLS (My Florida Regional MLS DBA Stellar MLS) (Listings courtesy of MFRMLS (My Florida Regional MLS DBA Stellar MLS) as distributed by MLS GRID)

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