26 Pleasant St, Annapolis, MD 21401
Local realty services provided by:O'BRIEN REALTY ERA POWERED
26 Pleasant St,Annapolis, MD 21401
$299,900
- 2 Beds
- 1 Baths
- 972 sq. ft.
- Townhouse
- Active
Listed by:matthew p wyble
Office:next step realty, llc.
MLS#:MDAA2125926
Source:BRIGHTMLS
Price summary
- Price:$299,900
- Price per sq. ft.:$308.54
About this home
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.
Contact an agent
Home facts
- Year built:1940
- Listing ID #:MDAA2125926
- Added:54 day(s) ago
- Updated:November 04, 2025 at 02:46 PM
Rooms and interior
- Bedrooms:2
- Total bathrooms:1
- Full bathrooms:1
- Living area:972 sq. ft.
Heating and cooling
- Cooling:Central A/C
- Heating:Forced Air, Natural Gas
Structure and exterior
- Year built:1940
- Building area:972 sq. ft.
- Lot area:0.02 Acres
Schools
- High school:ANNAPOLIS
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$299,900
- Price per sq. ft.:$308.54
- Tax amount:$2,499 (2024)
New listings near 26 Pleasant St
- Coming Soon
$689,000Coming Soon3 beds 3 baths1208 Darlow Pl, ANNAPOLIS, MD 21409
MLS# MDAA2130398Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY 
$870,000Pending3 beds 2 baths1,445 sq. ft.76 East St, ANNAPOLIS, MD 21401
MLS# MDAA2129526Listed by: COLDWELL BANKER REALTY- Coming SoonOpen Sat, 10:30am to 4pm
$1,247,900Coming Soon5 beds 4 baths1635 Winchester Rd, ANNAPOLIS, MD 21409
MLS# MDAA2130382Listed by: EQUITY PROPERTY INVESTMENTS - New
$3,395,000Active4 beds 4 baths3,750 sq. ft.48a E Lake Dr, ANNAPOLIS, MD 21403
MLS# MDAA2130372Listed by: EXP REALTY, LLC - New
$685,000Active3 beds 4 baths3,193 sq. ft.39 Windwhisper Ln, ANNAPOLIS, MD 21403
MLS# MDAA2130334Listed by: HOMESMART - Coming Soon
$499,999Coming Soon2 beds 2 baths2612 Quiet Water Cv #24, ANNAPOLIS, MD 21401
MLS# MDAA2130328Listed by: NEXT STEP REALTY, LLC. - Coming Soon
$220,000Coming Soon1 beds 1 baths10-b Sandstone Ct, ANNAPOLIS, MD 21403
MLS# MDAA2130272Listed by: RE/MAX EXECUTIVE - New
$950,000Active4 beds 4 baths2,659 sq. ft.319 Epping Way, ANNAPOLIS, MD 21401
MLS# MDAA2129940Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$489,900Active2 beds 2 baths1,318 sq. ft.78 Old Mill Bottom Rd N #107, ANNAPOLIS, MD 21409
MLS# MDAA2130318Listed by: MCWILLIAMS/BALLARD, INC. - New
$1,975,000Active3 beds 3 baths3,884 sq. ft.2 Southgate Ave #10, ANNAPOLIS, MD 21401
MLS# MDAA2129932Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
Protect your home and budget with an American Home Shield© home warranty. Learn more© 2023 - 2025 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.