105 21st Ave

Off Market

105 21st Ave

St. Pete Beach FL 33706

4377 sq. ft.

5001 sq. ft.

Single-Family

Last sold for $1,400,000

Brandon Tecklenburg, last sold this property on 01 October 2026 after 96 days on market.

Overview

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.

Features

5 bedrooms

4 bathrooms

3 carspaces

1 carport space

2 garage spaces

4377 sq. ft. floor area

5001 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in St. Pete Beach over the last 12 months, the estimated median property value of 105 21st Ave is $2.4m.

Median value

$2.4m

Estimated value range

$940k - $11m

Median days on market

100

Estimated value trend

78%

increase over the last 12 months

Average days on market is based on recent, comparable sales in St. Pete Beach. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 105 21st Ave

2026

Sold

$1,400,000

01 Oct 2026 by Brandon Tecklenburg, of EXP REALTY

2019

Sold

$740,000

08 Nov 2019 by Joan Walker, of SUNSHINE PROFESSIONAL REALTY

Happy sellers in St. Pete Beach

72%

72% of sellers in St. Pete Beach reported that their sale price either exceeded or met their price expectations.

St. Pete Beach stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 34 reviews in St. Pete Beach over the last 12 months.

Local market activity for 5 bedroom single-family properties in St. Pete Beach

In the last 12 months, 18 five-bedroom single-family properties similar to 105 21st Ave, have been sold.

This represents a 111% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in St. Pete Beach for a market analysis.

Jane McCroary

at REMAX Action First | St Petersburg

(201 reviews)

Get a market analysis

Anthony Russano, Jr

at TREASURE ISLAND REALTY LLC

(83 reviews)

Get a market analysis

Carol Giovannoni

at REMAX Preferred | St Pete Beach

(50 reviews)

Get a market analysis

Zach Sherf

at REMAX Advantage Realty | Baltimore

(44 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in St. Pete Beach

Jane McCroary

Sellers who recommend Jane McCroary have praised them for being local expert, responsive, clear communication, supportive, reliable, detail-oriented, and dedicated

5 (201 reviews)
15 Reviews in St. Pete Beach
12 Sales in St. Pete Beach

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Anthony Russano, Jr

Sellers who recommend Anthony Russano, Jr have praised them for being local expert, clear communication, supportive, reliable, great negotiation, responsive, and friendly

5 (83 reviews)
6 Reviews in St. Pete Beach
9 Sales in St. Pete Beach

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Carol Giovannoni

Sellers who recommend Carol Giovannoni have praised them for being local expert, clear communication, responsive, supportive, reliable, stress-free process, and trustworthy