Maryland
Annapolis
26 PLEASANT ST

$349,900

26 PLEASANT ST, Annapolis, MD 21401

2 beds |
1 bath |
972 sqft

Town Home
Built in 1940
871sqft lot
—— car garage
$360/sqft
Listed 2 days ago

Property Description

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.

Listing Status:: Active
Date Added:: September 11, 2025 at 05:00AM
Listing Office:: Next Step Realty, LLC. : 4439012200
Listing Agent:: Matthew P Wyble : 4105622325
MLS ID:: MDAA2125926

General: Breakfast AreaCeiling Fan(s)Combination Dining/LivingFloor Plan - OpenWood Floors
Rooms: Living RoomDining RoomKitchen
Appliances: RefrigeratorWasherDryerBuilt-In MicrowaveOven/Range - Gas
Laundry: Dryer In UnitWasher In Unit
Flooring: CarpetHardwood
A/C: Central A/C
Heating: Forced AirNatural Gas
Disability Feature: None

This listing courtesy of Matthew P Wyble, Next Step Realty, LLC.

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Annapolis Elementary School

180 Green St, Annapolis, MD, 21401

Grades PK-5

0.55 miles away

Mary Moss at Adams Academy

245 Clay St, Annapolis, MD, 21401

Grades 7-9

0.25 miles away

Annapolis High School

2700 Riva Rd, Annapolis, MD, 21401

Grades 9-12

3.66 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.