3/166 Pleasant Avenue

Portland ME 04103

835 sq. ft.

Condo

Last sold for $432,501

Christopher Davis, last sold this property on 27 February 2026 after -187 days on market.

Overview

Tucked into a quiet, tree-lined pocket of Deering Center, this sun-drenched two-bedroom, one-bath condo lives inside the historic Captain Matthews House—a home that feels storied, warm, and timeless the moment you step inside. Situated on the second floor, the space is filled with natural light thanks to oversized east- and south-facing windows. The kitchen and bathroom have been thoughtfully updated, blending classic character with modern comfort, and a heat pump ensures cool, easy living during Maine's warm summer months. The HOA covers heat and hot water, laundry is conveniently located on the first floor, and—rare for the neighborhood—this unit includes two private off-street parking spaces. Step outside and you're moments from everything that makes this area so special: peaceful walks through Evergreen Cemetery and Baxter Woods, plus some of Portland's most beloved local stops. Morning pastries at Norimoto Bakery, sandwiches from Pats Meat Market and Deli, coffee at Rambler Café, and pizza nights at Noble Pizzeria & BBQ—all just steps away. Offered for the first time in 25 years, this is a rare opportunity to own a piece of Deering Center history, where walkability, charm, and community come together beautifully.

Features

2 bedrooms

1 bathroom

835 sq. ft. floor area

Condo

Estimated Value

Based on this property and similar 2 bedroom condos sold in Portland over the last 12 months, the estimated median property value of 3/166 Pleasant Avenue is $410k.

Median value

$410k

Estimated value range

$295k - $661k

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Portland. 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 3/166 Pleasant Avenue

2026

Sold

$432,501

27 Feb 2026 by Christopher Davis, of Real Broker

Happy sellers in Portland

We have insufficient information to provide an overview of customer satisfaction for Portland. Viewing the agent profiles, reviews and sales for Portland can provide insights for this location.