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.
Sold for $275,000
$275,000
26 Pleasant St, Annapolis, MD 21401
2beds
972sqft
Townhouse
Built in 1940
864 Square Feet Lot
$278,200 Zestimate®
$283/sqft
$2,959 Estimated rent
Home value
$278,200
$259,000 - $298,000
$2,959/mo
Zestimate® history
Owner options
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$2,959/mo
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$2,959/mo
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$1,655/mo
Est. payment
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$1,655/mo
Est. payment
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List your homeWhat's special
Fenced backyardDining areaSpacious family roomTwo bedrooms
Zillow last checked:
Listing updated:
Listed by:
Matt Wyble 410-562-2325,
Next Step Realty
Bought with:
Bob Chew, 0225277244
Samson Properties
Kitty Papadopoulos, 5014235
Samson Properties
Source: Bright MLS,MLS#: MDAA2125926
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Dining room
- Level: Main
Kitchen
- Level: Main
Living room
- Level: Main
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Refrigerator, Washer, Dryer, Microwave, Oven/Range - Gas, Gas Water Heater
- Laundry: Dryer In Unit, Washer In Unit
Features
- Breakfast Area, Ceiling Fan(s), Combination Dining/Living, Open Floorplan
- Flooring: Carpet, Hardwood, Wood
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 972
- Total interior livable area: 972 sqft
- Finished area above ground: 972
- Finished area below ground: 0
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck
- Pool features: None
- Fencing: Chain Link
- Has view: Yes
- View description: Street
Lot
- Size: 864 sqft
- Features: Rear Yard
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020600003713100
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: Townhouse
- Architectural style: Traditional
- Property subtype: Townhouse
Materials
- Frame
- Foundation: Slab
Condition
- New construction: No
- Year built: 1940
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Location
- Region: Annapolis
- Subdivision: Annapolis
- Municipality: Annapolis
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Listing terms: Conventional,FHA,Cash,VA Loan
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 12/30/2025 | Sold | $275,000$283/sqft |
Source:  Bright MLS #MDAA2125926 Report a problem | ||
| 12/5/2025 | Contingent | $275,000$283/sqft |
Source: Bright MLS #MDAA2125926 Report a problem | ||
| 11/17/2025 | Price change | $275,000-8.3%$283/sqft |
Source: Bright MLS #MDAA2125926 Report a problem | ||
| 10/19/2025 | Price change | $299,900-7.7%$309/sqft |
Source: Bright MLS #MDAA2125926 Report a problem | ||
| 9/30/2025 | Price change | $324,900-7.1%$334/sqft |
Source: Bright MLS #MDAA2125926 Report a problem | ||
| 9/10/2025 | Listed for sale | $349,900+84.2%$360/sqft |
Source: Bright MLS #MDAA2125926 Report a problem | ||
| 3/29/2022 | Sold | $190,000+2.7%$195/sqft |
Source: Bright MLS #MDAA2020884 Report a problem | ||
| 2/9/2022 | Pending sale | $185,000$190/sqft |
Source: Bright MLS #MDAA2020884 Report a problem | ||
| 2/6/2022 | Listed for sale | $185,000+87.8%$190/sqft |
Source: Bright MLS #MDAA2020884 Report a problem | ||
| 5/12/2005 | Sold | $98,500+64.2%$101/sqft |
Source: Public Record Report a problem | ||
| 9/20/2002 | Sold | $60,000$62/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,747 +9.9% | $191,700 +10.2% |
| 2024 | $2,499 +11.5% | $173,900 +11.4% |
| 2023 | $2,242 +18.3% | $156,100 +16.1% |
| 2022 | $1,895 +19.2% | $134,467 +19.2% |
| 2021 | $1,590 +23.6% | $112,833 +23.7% |
| 2020 | $1,286 +0.5% | $91,200 |
| 2019 | $1,280 +2% | $91,200 +1.1% |
| 2018 | $1,255 +7.2% | $90,200 +0.6% |
| 2017 | $1,171 | $89,700 |
| 2016 | -- | $89,700 |
| 2015 | -- | $89,700 -3.5% |
| 2014 | -- | $93,000 |
| 2013 | -- | $93,000 |
| 2012 | -- | $93,000 -21.8% |
| 2011 | -- | $118,870 |
| 2010 | -- | $118,870 |
| 2009 | -- | $118,870 -11.3% |
| 2008 | -- | $133,950 +20.1% |
| 2007 | -- | $111,486 +25.2% |
| 2006 | -- | $89,023 +33.7% |
| 2005 | -- | $66,560 +0.7% |
| 2004 | -- | $66,080 +0.7% |
| 2003 | -- | $65,600 +0.7% |
| 2002 | -- | $65,120 |
| 2001 | -- | $65,120 |
Find assessor info on the county website
Neighborhood: 21401
Nearby schools
GreatSchools rating
- 5/10Annapolis Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 5/10Wiley H. Bates Middle SchoolGrades: 6-8Distance: 0.6 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 3.7 mi
Schools provided by the listing agent
- High: Annapolis
- District: Anne Arundel County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$278,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$278,200
- Maryland
- Anne Arundel County
- Annapolis
- 21401
- 26 Pleasant St
Nearby cities
Nearby zip codes
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