Search

Nearby Properties

105 21ST AVE,  ST PETE BEACH, FL 33706

MLS# TB8520827.  5 beds.  4.0 baths.  Single Family Home.  Active

$14,667 in taxes (2025)

$1,500,000   Increased by $100,000 (6.7%)

 

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.

Quick Info:

  • Listing is courtesy Of: EXP REALTY ((727-592-2286))
  • Listing Agent: Brandon Tecklenburg ((727-265-6269))
  • Days on yellowkey: 11
  • Property Type: Single Family Home
  • Beds: 5
  • Baths: 4.0
  • Living Area Square Feet: 2765
  • Built 1934
  • Taxes: $14,667 (2025)
  • Garage Spaces:2 ()
  • Square Feet: 4377
  • Fees: $0
  • Pinellas County
  • Terms: Cash, Conventional
  • Subdivision Info:
  • Occupancy Information: Tenant
  • Community:
  • Membership Purchase Required:
  • Development Name:
  • Subdivision Name: PHILLIPS DIV REV MAP
  • Complex Name:

Interior Details:

  • Interior Levels:
  • Stories:
  • Bedroom Description:
  • Master Bathroom Description:
  • Interior Features: Ceiling Fans(s), Stone Counters
  • Dining Description:
  • Floor:
  • Cooling:
  • Heating:
  • Equipment/Appliances:
  • Other Rooms:
  • Windows Treatment:
  • Cable Available
  • Water Utility:

Exterior/Other Details:

  • Design:
  • Design Description:
  • Guest House Living Area:
  • Guest House Description:
  • Efficiency:
  • Unit Floor Location:
  • Guest House Description:
  • Garage Description:
  • Carport Spaces: 1
  • Carport Description:
  • Parking Description: Garage Faces Rear
  • Pool Description:
  • Pool Dimensions:
  • Lot:
  • Front Exposure:
  • Exterior Features: Balcony, French Doors, Outdoor Shower, Rain Gutters
  • Roof Description:
  • Security:
  • Sprinkler:
  • Sewer Description:
  • Miscellaneous:
  • View:
  • Waterfront Front:
  • Waterfront Description:
  • Water Access:

History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
6/30/2026Sale3TB8520827Price Change$1,500,0007.14%342.7004MLS
6/26/2026Sale0TB8520827listed for sale$1,400,000-319.8537MLS




Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.