Property
ActiveResidential
1/60
$1,500,000

105 21ST AVENUE

St Pete Beach, FL 33706
5
Beds
4
Baths
2,765
SqFt
0.11
Acres
STELLAR
#TB8520827
Updated: Jun 30, 2026, 6:38pm

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.
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Included Appliances
Disposal

Property Details

Interior
Additional Rooms
Bonus Room
Appliances
Disposal
Bathrooms Total Decimal
4
Building Area Total
4377
Cooling
Central Air
Fireplace Features
Wood Burning
Flooring
Luxury VinylTile
Furnished
Furnished
Heating
Central
Interior Features
Ceiling Fan(s)Stone Counters
Laundry Features
Inside
Living Area
2765
Rooms Total
3
Window Features
Blinds
Construction
Building Area Source
Appraiser
Building Area Units
Square Feet
Construction Materials
Wood FrameWood Siding
Direction Faces
South
Foundation Details
Pillar/Post/Pier
Levels
Two
Living Area Source
Appraiser
Living Area Units
Square Feet
Num Timesper Year
12
Roof
Metal
Stories Total
2
Year Built
1934
Site & Exterior
Carport Spaces
Yes
Covered Spaces
3
Exterior Features
BalconyFrench DoorsOutdoor ShowerRain Gutters
Fencing
FencedVinyl
Flood Zone Code
AE
Garage Dimensions
26x17
Garage Spaces
2
I D X Participation
Yes
Lot Features
Historic DistrictNear Golf CourseNear MarinaNear Public TransitSidewalk
Lot Size Acres
0.11
Lot Size Area
5001
Lot Size Dimensions
50 x 100
Lot Size Square Feet
5001
Lot Size Units
Square Feet
Other Structures
Guest House
Parking Features
Garage Faces Rear
Patio And Porch Features
CoveredEnclosedPatio
Public Survey Range
16
Public Survey Section
18
Road Surface Type
Asphalt
Sewer
Public Sewer
Total Acreage
0 to less than 1/4
Utilities
Cable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
Water Source
Public
Financials
Calculated List Price By Calculated Sq Ft
542.5
Contract Status Change Date
2026-06-26
Current Price
1500000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
1 Month
Owner Name
PINEAPPLE HOUSE PAG LLC
Ownership
Fee Simple
Parcel Number
183216686340100680
Public Survey Township
32
Tax Annual Amount
14666.84
Tax Block
J
Tax Book Number
3-38
Tax Legal Description
PHILLIPS DIVISION REV MAP BLK J, LOT 68
Tax Lot
68
Tax Year
2025

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
Can be leased less than 30 days 3 times per yearafter that 30 day minimum rentals
Lease Restrictions
Yes
M L S Area Major
33706 - Pass a Grille Bch/St Pete Bch/Treasure Isl
Pets Allowed
Yes
Subdivision Name
PHILLIPS DIV REV MAP
Schools
Ratings
Elementary
Azalea Elementary-PN
Middle
Bay Point Middle-PN
High
Boca Ciega High-PN
Listing provided courtesy of STELLAR via IDX. Updated: Jun 30, 2026, 6:38pm.
Brandon Tecklenburg

Listing Agent

EXP REALTY

Call Agent