Back 26 Pleasant Street
Off Market

26 Pleasant Street

Annapolis MD 21401

2
1
972 sq. ft.
864 sq. ft.
Townhouse
Last sold for $275,000
Matt WybleMatt Wyble, last sold this property on 30 December 2025 after 110 days on market.

Overview

NEW PRICE! Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife. Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025. Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft area for an office or guest space. Don’t miss your chance to own an Annapolis gem with walkable lifestyle perks and a track record of short-term rental success.

Features

2 bedrooms
1 bathroom
972 sq. ft. floor area
864 sq. ft. lot size
Townhouse

Estimated Value

Based on this property and similar 2 bedroom townhouses sold in Annapolis over the last 12 months, the estimated median property value of 26 Pleasant Street is $477.5k.

Median value
$477.5k
Estimated value range
$245k - $865k
Median days on market
12
Estimated value trend
6%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Annapolis. 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 26 Pleasant Street

2025
Sold
$275,000
30 Dec 2025 by Matt Wyble, of Next Step Realty, LLC.
2022
Sold
$190,000
29 Mar 2022 by Tony Annello, of Keller Williams Gateway LLC

Happy sellers in Annapolis

96%
96% of sellers in Annapolis reported that their sale price either exceeded or met their price expectations.

Annapolis stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 13 reviews in Annapolis over the last 12 months.

Local market activity for 2 bedroom townhouses in Annapolis

In the last 12 months, 48 two-bedroom townhouses similar to 26 Pleasant Street, have been sold.

This represents a 7% increase in two-bedroom townhouses sales when compared to the previous 12 months.

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