About Home value Property history Tax history Market statistics Schools Neighborhood Places of interest

26 Pleasant St, Annapolis, MD 21401

$275,000

Last sold 12/30/2025 after 111 Days

2
bed
1
bath
972
Sqft ($283/Sqft)

Townhouse not for sale

About 26 Pleasant St

Property type Townhouse

Neighborhood

Year built 1940

HOA fee $0/month

Lot size 864 Sqft

Movoto estimate

Rental estimate

Property description

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.

Listed by

Listing Agent - Matthew P Wyble

Listing Office - Next Step Realty, LLC.

Source: Bright MLS

MLS#MDAA2125926 • last updated 10 months ago

Movoto checked Bright MLS for data 6 minutes ago

Overview
Cooling/AC	Central A/C, Electric
Heating	Natural Gas
Levels/Style	Traditional
Type	Residential
Virtual Tour	N/A
Status	Closed
SqFt	972
Lot Size (SqFt)	864
Lot Size (Acres)	0.02
County Tax	1216, Annually
City/ Town Tax	1283
Tax: Assessed Value	191700
Annual Property Tax	2499
Year Built	1940
Municipality	Annapolis
New Construction (Y/N)	N
Foreclosure (Y/N)	N

Interior
Total # of Bathrooms	1
# Full Baths	1
Total # of Bedrooms	2
Other Room(s)	Living Room, Dining Room, Kitchen
Appliances	Refrigerator, Washer, Dryer, Built-In Microwave, Oven/Range - Gas
Interior Features	Breakfast Area, Ceiling Fan(s), Combination Dining/Living, Floor Plan - Open, Wood Floors
Accessibility Features	None

Exterior
Construction	Frame
Foundation	Slab
Parking Desc	On Street
Existing Structures	Above Grade, Below Grade, Deck(s)
Lot Desc	Rear Yard
Fencing	Chain Link

Amenities / Utilities
Sewer/ Septic	Public Sewer
Pool	No Pool

Location
View	Street
Subdivision	ANNAPOLIS
Water Source	Public
Senior Community (Y/N)	N
High School	ANNAPOLIS
School District	ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Directions	GPS
Zoning	R

$293K

Range: $269K-$318K

Last 30 days

Rental est.: $1,843/month

• Gross rent multiplier: 12.4

Lower your payment with the loan terms that fit you.

Jan 2026
Public Records
Jan 29, 2026 Sold
$275,000
Dec 2025
MLS # MDAA2125926
Dec 30, 2025 Sold
$275,000
Dec 5, 2025 Active
—
Nov 17, 2025 Price Change
$275,000 (-8.3%)
Oct 18, 2025 Price Change
$299,900 (-7.7%)
Sep 29, 2025 Price Change
$324,900 (-7.1%)
Sep 10, 2025 Listed
$349,900 (+84.2%)
Apr 2022
Public Records
Apr 6, 2022 Sold
$190,000
Mar 2022
MLS # MDAA2020884
Mar 29, 2022 Sold
$190,000 (+2.7%)
Feb 9, 2022 Pending
—
Feb 5, 2022 Listed
$185,000 (+87.8%)
May 2005
Public Records
May 12, 2005 Sold
$98,500 (+64.2%)
Sep 2002
Public Records
Sep 20, 2002 Sold
$60,000

Year Property taxes Tax assessment
2025
$2,747 +22.5%

$191,700 +10.24%
2023
$2,242 +18.3%

$173,900 +29.33%
2022
$1,895 +51.0%

$134,467 +19.17%
2018
$1,255 +7.2%

$112,833 +25.79%
2017
$1,171

$89,700

26 Pleasant St
$275K
Annapolis
—
21401
$719K +3% y/y
Annapolis
$695K 0% y/y

No chart available

Statistics calculated by Movoto

	Est. value	Bed/bath	Sqft	mi
40 Pleasant St, Annapolis, MD 21401	$291,800	3/1	910	0
24 Pleasant St, Annapolis, MD 21401	$308,000	—/1	840	0
38 Pleasant St, Annapolis, MD 21401	$291,900	2/1	840	0
36 Pleasant St, Annapolis, MD 21401	$258,000	—/1	912	0.01
34 Pleasant St, Annapolis, MD 21401	$299,200	—/1	972	0.01
32 Pleasant St, Annapolis, MD 21401	$281,700	—/2	984	0.01
30 Pleasant St, Annapolis, MD 21401	$318,700	3/1	840	0.01
28 Pleasant St, Annapolis, MD 21401	$255,900	1/1	816	0.02

Estimated values are based on public record data and automated valuation models. Values are not guaranteed and may not reflect current market conditions.