105 21ST AVENUE, ST PETE BEACH, FL, 33706
Active38 days on marketListed Jun 26, 2026MLS #TB8520827
About this home
105 21ST AVENUE
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.
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
2,765
Sqft
0.11 ac
Lot size
2
Garage
1934
Year built
Two
Levels
$542
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$10,039 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$10,039/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs St Pete Beach actives
$542 vs $509
Days on market
38 vs 85 typical
Where $542/sqft sits among the 177 St Pete Beach actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Pass-a-grille Beach
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know St Pete Beach. See the full St Pete Beach guide →
Pass-a-grille Beach — neighborhood snapshot
Population
824
Median age
61
Median income
$106,407
Median home value
$748,033
Avg household
2
Households w/ children
66%
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The St Pete Beach market
$679K → $589K
St Pete Beach median sold, yr/yr
93.3%
Sale-to-list ratio (12 mo)
86 of 177
St Pete Beach actives have cut their price
Median sold price, St Pete Beach, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 233% above the ST PETE BEACH 33706 median. See the full St Pete Beach market guide →
Paper trail
This home's history
Reality check
What actually sold near 105 21ST AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$1,914,000
106 19TH AVENUE · same community
2 bd · 2 ba · 2,135 sqft · $896/sqft · 137 DOM
Sold · Dec ’25$3,430,000
2003 GULF WAY · same community
4 bd · 3.5 ba · 2,006 sqft · $1,710/sqft · 9 DOM
Sold · Jun ’26$875,000
104 18TH AVENUE · same community
4 bd · 2 ba · 1,218 sqft · $718/sqft · 29 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 105 21ST AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 105 21ST AVENUE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
105 21ST AVENUE FAQs
What would the monthly payment be for 105 21ST AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $10,039/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 105 21ST AVENUE?+
The most recent tax bill on record (2025) was $14,667. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 105 21ST AVENUE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in St Pete Beach?+
At $1,500,000, this home is listed about 150% above the St Pete Beach median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 105 21ST AVENUE?+
Boca Ciega High School (high), Bay Point Middle School (middle), Azalea Elementary School (elementary) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$1,500,000 runs 233% above the ST PETE BEACH 33706 median — but at 2,765 sqft it's also nearly twice the size of the typical St Pete Beach listing.
02Move-in furnished
The furniture conveys — a genuine head start for a second home or rental, and one less five-figure line item after closing.
03Strong assigned schools
Boca Ciega High School, Bay Point Middle School, Azalea Elementary School — Azalea Elementary School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of EXP REALTY · Brandon Tecklenburg. MLS #TB8520827.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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