105 21ST AVENUE, Saint Pete Beach, FL, 33706
About This Home
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.
Getting Around
Somewhat Walkable
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1934
Materials
- Foundation: Pillar/Post/Pier
- Roof: Metal
- Construction materials: Wood Frame,Wood Siding
Type & Style
- Home type: SingleFamily
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Disposal
- Laundry features: Inside
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
Features
- Ceiling Fan(s),Stone Counters
- Door features: French Doors,Outdoor Shower
- Flooring: Luxury Vinyl,Tile
- Fireplace features: Wood Burning
- Fireplace: Yes
Heating & Cooling
- Heating features: Central
- Cooling features: Central Air
Interior Area
- Total structure area: 4,377
- Total interior livable area: 2,765 sqft
Kitchen
- Level: First
- Area: 116.96
- Dimensions: 13.6x8.6
Living Room
- Level: First
- Area: 202.64
- Dimensions: 13.6x14.9
Primary Bedroom
- Features: Bath With Whirlpool,En Suite Bathroom,Built-in Closet
- Level: Second
- Area: 654.5
- Dimensions: 38.5x17
Property
Details
- Parcel number: 183216686340100680
- Special condition: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered,Enclosed,Patio
- Exterior features: Balcony,Outdoor Shower,Rain Gutters
- Fencing: Fenced,Vinyl
Lot
- Lot size: 5,001 sqft
- Features: Historic District,Near Golf Course,Near Marina,Near Public Transit,Sidewalk
- Lot size dimensions: 50 x 100
Parking
- Total spaces: 3
- Parking features: Garage Faces Rear
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 3
- Carport: Yes
- Carport spaces: 1
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Coastal Flooding
- Hurricane
- Lightning
- Cold Wave
- Tornado
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters in Pinellas County and Florida
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $7,584 | $91,008 |
| Home Insurance * | $1,619 | $19,428 |
| Property Taxes | $2,009 | $24,108 |
| Electricity | $278 | $3,339 |
| Total | $11,490 | $137,880 |
Income You'd Need if You Spent...
Florida FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-08-11 | Listed for sale | $1,500,000 |
| 2026-08-06 | Contingent | $1,500,000 |
| 2026-06-30 | Price change | $1,500,000 |
| 2026-06-26 | Listed for sale | $1,400,000 |
| 2026-05-17 | Price change | $6,000 |
| 2026-03-13 | Price change | $6,500 |
| 2025-10-24 | Listed for rent | $7,000 |
| 2024-09-28 | Listing removed | $15,000 |
| 2024-09-01 | Listed for rent | $15,000 |
| 2024-08-17 | Listing removed | -- |
| 2024-06-20 | Price change | $5,000 |
| 2024-05-05 | Price change | $5,500 |
| 2024-04-22 | Price change | $5,750 |
| 2024-02-11 | Listed for rent | $6,000 |
| 2023-04-07 | Listing removed | -- |
| 2023-02-24 | Price change | $5,500 |
| 2022-11-09 | Price change | $6,000 |
| 2022-10-20 | Price change | $6,500 |
| 2022-09-04 | Price change | $6,000 |
| 2022-08-11 | Price change | $6,250 |
| 2022-07-11 | Price change | $6,500 |
| 2022-06-27 | Price change | $7,000 |
| 2022-05-25 | Price change | $7,500 |
| 2022-05-03 | Price change | $8,000 |
| 2022-04-07 | Listed for rent | $7,000 |
| 2019-11-12 | Sold | $740,000 |
| 1995-06-08 | Sold | $185,000 |
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