105 21ST AVENUE
St Pete Beach, FL 33706
$1,400,000
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 ...
Listing Courtesy of: EXP REALTY
727-592-2286
Buyer Represented by: COMPASS FLORIDA LLC
| Listing Id: | TB8520827 |
|---|---|
| List Price: | $1,500,000 |
| Close Price: | $1,400,000 |
| Close Date: | 2026-10-01 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 5 |
| Bathrooms Full: | 4 |
| Living Area: | 2,765 |
| Tax Annual Amount: | $14,667 |
| Lot Size Square Feet: | 5,001 |
| Lot Size Acres: | 0.11 |
| Waterfront?: | No |
| City: | St Pete Beach |
| County Or Parish: | Pinellas |
| Subdivision Name: | Phillips Div Rev Map |
| Postal Code: | 33706 |
| Year Built: | 1934 |
| Appliances: | Disposal |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 4 |
| Building Area Source: | Appraiser |
| Building Area Total: | 4377 |
| Building Area Units: | Square Feet |
| Carport Spaces: | 1 |
| Carport?: | Yes |
| Direction Faces: | South |
| Foundation Details: | Pillar/Post/Pier |
| Construction Materials: | Frame, Wood Siding |
| Cooling: | Central Air |
| Fireplace Features: | Wood Burning |
| Directions: | 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 |
| Elementary School: | Azalea Elementary-PN |
| Exterior Features: | Balcony, Outdoor Shower, Rain Gutters |
| Fencing: | Fenced, Vinyl |
| Flooring: | Luxury Vinyl, Tile |
| Furnished: | Furnished |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Heating: | Central |
| High School: | Boca Ciega High-PN |
| Interior Features: | Ceiling Fans(s), Stone Counters |
| Laundry Features: | Inside |
| Levels: | Two |
| Listing Contract Date: | 2026-08-05 |
| Ownership: | Fee Simple |
| Living Area Source: | Appraiser |
| Living Area Units: | Square Feet |
| Lot Features: | Historic District, Near Golf Course, Near Marina, Near Public Transit, Sidewalk |
| Lot Size Acres: | 0.11 |
| Lot Size Dimensions: | 50x100 |
| Postal Code Plus4: | 4103 |
| Middle Or Junior School: | Bay Point Middle-PN |
| MLS Area Major: | 33706 - Pass A Grille Bch/St Pete Bch/Treasure Isl |
| MLS Area Major: | 33706 - Pass a Grille Bch/St Pete Bch/Treasure Isl |
| Other Structures: | Guest House |
| Original List Price: | $1,400,000 |
| Parcel Number: | 18-32-16-68634-010-0680 |
| Parking Features: | Garage Faces Rear |
| Patio And Porch Features: | Covered, Enclosed, Patio |
| Pets Allowed: | Yes |
| Stories Total: | 2 |
| Township: | 32 |
| Road Surface Type: | Asphalt |
| Roof: | Metal |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected |
| Water Source: | Public |
| Public Survey Range: | 16 |
| Public Survey Section: | 18 |
| Window Features: | Blinds |
| Additional Lease Restrictions: | Can be leased less than 30 days 3 times per year, after that 30 day minimum rentals |
| Additional Rooms: | Bonus Room |
| Alternate Key Folio Num: | 183216686340100680 |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | Yes |
| Building Area Total Srch Sq M: | 406.64 |
| Calculated List Price By Calcula: | 542.50 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/TB8520827?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/TB8520827?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | Yes |
| Flood Zone Code: | AE |
| Flood Zone Date: | 2021-08-24 |
| Flood Zone Panel: | 12103C0278H |
| Garage Dimensions: | 26x17 |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 256.88 |
| Lot Size Square Meters: | 465 |
| Minimum Lease: | 1 Month |
| Month To Month Or Weekly Yn: | Yes |
| Num Times per Year: | 12 |
| Realtor Info: | As-Is |
| Room Count: | 3 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Association 2 Yn: | 0 |
| Attribution Contact: | 727-592-2286 |
| Originating System Name : | Stellar MLS |
| Dock Yn: | No |
| In Law Suite Description: | 2+ Bathrooms, 2+ Bedrooms |
| In Law Suite Yn: | Yes |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-06-25 |
| Fireplace?: | Yes |
Mortgage Calculator
Copyright 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. Information deemed reliable but is not guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of My Florida Regional MLS DBA Stellar MLS. Real estate listings held by brokerage firms other than the owner of this page include the name of the listing broker. Information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This site will be monitored for 'scraping' and any use of search facilities of data on the site other than by a consumer looking to purchase real estate is prohibited. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on October 16, 2026 02:36 AM - ET
Based on information submitted to the MLS GRID as of October 16, 2026 02:36 AM - ET. 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. Properties displayed may be listed or sold by various participants in the MLS. Some listings have been excluded from this website.
IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.
Property Last Updated: October 16, 2026 02:36 AM - ET
