105 21st Ave,ST PETE BEACH, FL 33706
ST PETE BEACH, FL 33706
Description
Under contract-accepting backup offers. 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.
Details
| MLS # | TB8520827 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | For-sale |
| Status | Active Under Contract |
| Year | 1934 |
| Days On Site | 79 |
| Listing Provided By | EXP REALTY | Brandon Tecklenburg |
Features
| Bed(s) | 5 |
|---|---|
| Bath(s) | 4 Total |
| SQ Feet | 2,765 |
| Garage | 2 |
| Car Port | Yes |
| Story(s) | 2 |
| Acreage | 0.11 |
| Golf Course | Yes |
Taxes
| Property | 14666 |
|---|
Area Information
| State | FL |
|---|---|
| County | Pinellas |
| City | ST PETE BEACH |
| Zip Code | 33706 |
| Area | 33706 Pass a Grille Bch | St Pete Bch | Treasure Isl |
| Community Name | PHILLIPS DIV REV MAP |
| School District | Boca Ciega High-PN |
| Elementary School | Azalea Elementary-PN |
| High School | Boca Ciega High-PN |
| Listing VS Median (in PHILLIPS DIV REV MAP) | |
Price: $1,500,000 low | high Med: $2,200 sqft: 2,765 low | high Med: 780 $ / sqft: $542 low | high Med: $3 On site: 79 low | high Med: 120 | |
Market Activity 33706
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Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 13, 2026 at 12:44:21 PM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
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Learn More About This Property
| State | FL |
|---|---|
| County | Pinellas |
| City | ST PETE BEACH |
| Zip Code | 33706 |
| Area | 33706 Pass a Grille Bch | St Pete Bch | Treasure Isl |
| Community Name | PHILLIPS DIV REV MAP |
| School District | Boca Ciega High-PN |
| Elementary School | Azalea Elementary-PN |
| High School | Boca Ciega High-PN |
| Listing VS Median (in PHILLIPS DIV REV MAP) | |
Price: $1,500,000 low | high Med: $2,200 sqft: 2,765 low | high Med: 780 $ / sqft: $542 low | high Med: $3 On site: 79 low | high Med: 120 | |
 | $2,300,000109 14th AveSt Pete Beach, FL 33706 |
 | $1,700,0001304 Pass A Grille WaySt Pete Beach, FL 33706 |
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
