SoldDec 30, 2025

Listed by Matt Wyble

Bought with Bob Chew

Source: Bright MLS #MDAA2125926

26 Pleasant Street, Annapolis, MD, 21401

$275,000

2
1
972 sq. ft.
864 sq. ft.

Townhouse

30+ days on the market

Sold: Dec 30, 2025

What's around 26 Pleasant Street

About this property

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.

Looking for more information on 26 Pleasant Street?

Explore comparables, sales history and growth for this property.
Learn more

Contact

Similar properties sold nearby

SoldSep 4, 2026
$540,000
1006 Dreams Landing Way
Parole MD 21401
2
2
Townhouse
Listing courtesy of Cummings & Co. Realtors and Long & Foster Real Estate, Inc.
SoldSep 1, 2026
$475,000
2627 Compass Drive
Parole MD 21401
2
2
2
Townhouse
Listing courtesy of Rosendale Realty and Berkshire Hathaway HomeServices PenFed Realty
SoldJul 31, 2026
$540,000
2607 Compass Drive
Parole MD 21401
2
3
2
Townhouse
Listing courtesy of Academy Realty Inc. and REMAX Distinctive New Home Team | Baltimore

Other properties sold by Next Step Realty, LLC.

SoldSep 4, 2026
$899,000
6456 Meadowlark Drive
Dunkirk MD 20754
5
5
22
Single-Family
Listing courtesy of RE/MAX One and Next Step Realty, LLC.
SoldSep 4, 2026
$2,300,000
104 Bellehahn Court
Arnold MD 21146
6
7
9
Single-Family
Listing courtesy of Next Step Realty, LLC. and Engel & Völkers Annapolis
SoldSep 3, 2026
$224,500
905 Hanover Street
Salisbury MD 21801
3
2
2
Single-Family
Listing courtesy of Campos International Group and Next Step Realty, LLC.

Browse properties sold in nearby areas

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Next Step Realty, LLC. participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

© 2026 RateMyAgent