Timeless Elegance in the Heart of Historic Annapolis. Tucked away on one of Annapolis’ most charming streets, this circa-1900 home blends historic character with thoughtful, high-end renovations. Painted deep navy cedar shingles with crisp white trim, this unique home sits gracefully along a brick-paved sidewalk, just steps from the waterfront, the U.S. Naval Academy, and downtown’s best restaurants, coffee shops, and boutiques. Inside, a sense of history lingers with colonial heart pine hardwood floors, original brickwork, and detailed millwork, while modern updates bring effortless style. The family room, with its bay window and plantation shutters, offers a bright, inviting space. Beyond it, the dining room, anchored by custom built-ins that discreetly house a wet bar, wine and beverage refrigerators, and an ice maker is ideal for entertaining. The gourmet kitchen, a showpiece, balancing warmth and sophistication with marble counters, brass and leather hardware, and a custom hood set into an old brick chimney—now framing a Wolf gas range. A paneled Sub-Zero refrigerator and Bosch dishwasher blend seamlessly into the cabinetry. French doors open to a large private brick patio, where lush landscaping creates a peaceful retreat with plenty of room to entertain or relax with close friends and family. The primary suite on the second floor features an en-suite bath, with a dual sink, a make up vanity and a large walk in shower. The laundry room is also conveniently located on this level, along with a second full bath and bedroom. The third floor offers two additional bedrooms connected by a Jack-and-Jill bath. Registered in both the Annapolis and National Historic Districts, this home is a rare blend of period charm and modern ease—a place where history meets everyday comfort in the most effortless way.
Sold for $1,425,000
$1,425,000
144 Charles St, Annapolis, MD 21401
4beds
2,089sqft
Single Family Residence
Built in 1900
1,980 Square Feet Lot
$1,448,600 Zestimate®
$682/sqft
$3,859 Estimated rent
Home value
$1,448,600
$1.35M - $1.56M
$3,859/mo
Zestimate® history
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List your homeWhat's special
Original brickworkCharming streetsCustom built-insFrench doorsPrivate brick patioDual sinkDetailed millwork
Zillow last checked:
Listing updated:
Listed by:
Kate Hopkins 410-703-8502,
Coldwell Banker Realty,
Listing Team: Let's Move Crew, Co-Listing Team: Let's Move Crew,Co-Listing Agent: Elizabeth S Montaner 443-871-1143,
Coldwell Banker Realty
Bought with:
Kristen Boyer, 680858
Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS,MLS#: MDAA2106388
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Primary bedroom
- Features: Flooring - HardWood, Attached Bathroom, Window Treatments, Ceiling Fan(s)
- Level: Upper
Bedroom 2
- Features: Flooring - HardWood, Built-in Features, Window Treatments
- Level: Upper
Bedroom 3
- Features: Flooring - HardWood, Window Treatments, Attached Bathroom
- Level: Upper
Bedroom 4
- Features: Flooring - HardWood, Attached Bathroom, Window Treatments
- Level: Upper
Primary bathroom
- Features: Double Sink, Bathroom - Walk-In Shower, Flooring - Ceramic Tile, Flooring - Tile/Brick, Built-in Features
- Level: Upper
Bathroom 1
- Level: Main
Bathroom 2
- Features: Flooring - Ceramic Tile, Flooring - Tile/Brick, Bathroom - Tub Shower
- Level: Upper
Bathroom 3
- Features: Jack and Jill Bathroom, Bathroom - Stall Shower, Built-in Features, Flooring - Ceramic Tile, Flooring - Tile/Brick
- Level: Upper
Basement
- Features: Basement - Unfinished
- Level: Lower
Dining room
- Features: Flooring - HardWood, Built-in Features, Wet Bar, Window Treatments
- Level: Main
Family room
- Features: Flooring - HardWood, Window Treatments, Ceiling Fan(s), Recessed Lighting
- Level: Main
Kitchen
- Features: Attached Bathroom, Breakfast Bar, Built-in Features, Countertop(s) - Quartz, Dining Area, Flooring - HardWood, Eat-in Kitchen, Kitchen - Gas Cooking, Lighting - Ceiling
- Level: Main
Laundry
- Level: Upper
Heating
- Radiator, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Disposal, Dryer, Oven/Range - Gas, Refrigerator, Washer, Dishwasher, Gas Water Heater
- Laundry: Upper Level, Washer In Unit, Dryer In Unit, Has Laundry, Laundry Room
Features
- Breakfast Area, Built-in Features, Crown Molding, Dining Area, Kitchen - Gourmet, Primary Bath(s), Upgraded Countertops
- Flooring: Hardwood, Ceramic Tile, Wood
- Doors: French Doors
- Windows: Wood Frames
- Basement: Unfinished
- Has fireplace: No
Interior area
- Total structure area: 2,689
- Total interior livable area: 2,089 sqft
- Finished area above ground: 2,089
- Finished area below ground: 0
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Patio
- Exterior features: Extensive Hardscape, Lighting
- Pool features: None
Lot
- Size: 1,980 sqft
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020600002422507
- Zoning: RESIDENTIAL
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
- Attached to another structure: Yes
Materials
- Other, Wood Siding
Condition
- Excellent
- New construction: No
- Year built: 1900
- Major remodel year: 2023
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Available, Natural Gas Available, Sewer Available, Water Available
Community & neighborhood
Location
- Region: Annapolis
- Subdivision: Historic District
- Municipality: Annapolis
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 4/29/2025 | Sold | $1,425,000+5.6%$682/sqft |
Source:  Bright MLS #MDAA2106388 Report a problem | ||
| 4/10/2025 | Pending sale | $1,350,000$646/sqft |
Source: Bright MLS #MDAA2106388 Report a problem | ||
| 4/4/2025 | Listed for sale | $1,350,000+64.8%$646/sqft |
Source: Bright MLS #MDAA2106388 Report a problem | ||
| 12/7/2020 | Sold | $819,093$392/sqft |
Source: Public Record Report a problem | ||
| 6/24/2020 | Sold | $819,093-2.4%$392/sqft |
Source: Agent Provided Report a problem | ||
| 5/27/2020 | Pending sale | $839,000$402/sqft |
Source: Monument Sotheby's International Realty #MDAA426006 Report a problem | ||
| 2/26/2020 | Listed for sale | $839,000+19.9%$402/sqft |
Source: Monument Sotheby's International Realty #MDAA426006 Report a problem | ||
| 3/25/2015 | Sold | $700,000-2.8%$335/sqft |
Source: Public Record Report a problem | ||
| 1/30/2015 | Pending sale | $719,900$345/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8475115 Report a problem | ||
| 10/8/2014 | Listed for sale | $719,900+12.7%$345/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8475115 Report a problem | ||
| 6/28/2011 | Sold | $639,000-7.4%$306/sqft |
Source: Public Record Report a problem | ||
| 6/8/2011 | Listed for sale | $689,900$330/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA7551605 Report a problem | ||
| 4/29/2011 | Listing removed | $689,900$330/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA7551605 Report a problem | ||
| 3/15/2011 | Listed for sale | $689,900-1.4%$330/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA7551605 Report a problem | ||
| 12/4/2010 | Listing removed | $699,900$335/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 10/30/2010 | Price change | $699,900+0%$335/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 10/10/2010 | Price change | $699,8900%$335/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 9/8/2010 | Price change | $699,900-5.4%$335/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 8/27/2010 | Price change | $739,900-5.1%$354/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 6/27/2010 | Price change | $779,8000%$373/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 4/8/2010 | Listed for sale | $779,900+140%$373/sqft |
Source: NRT MidAtlantic #AA7300805 Report a problem | ||
| 2/26/1999 | Sold | $325,000$156/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $12,431 +9.4% | $867,467 +9.7% |
| 2024 | $11,366 +10.8% | $790,933 +10.7% |
| 2023 | $10,259 +2% | $714,400 +0% |
| 2022 | $10,062 +0% | $714,133 +0% |
| 2021 | $10,058 0% | $713,867 +0% |
| 2020 | $10,062 +5.3% | $713,600 |
| 2019 | $9,556 +7.2% | $713,600 +11.3% |
| 2018 | $8,914 +13% | $640,867 +6% |
| 2017 | $7,889 | $604,500 +2.8% |
| 2016 | -- | $587,933 +2.9% |
| 2015 | -- | $571,367 +3% |
| 2014 | -- | $554,800 |
| 2013 | -- | $554,800 |
| 2012 | -- | $554,800 -8.5% |
| 2011 | -- | $606,490 +0.2% |
| 2010 | -- | $605,220 +0.2% |
| 2009 | -- | $603,950 +0.2% |
| 2008 | -- | $602,680 +16.4% |
| 2007 | -- | $517,892 +19.6% |
| 2006 | -- | $433,106 +24.3% |
| 2005 | -- | $348,320 +13.6% |
| 2004 | -- | $306,632 +15.7% |
| 2003 | -- | $264,946 +18.7% |
| 2002 | -- | $223,260 +6.5% |
| 2001 | -- | $209,676 |
Find assessor info on the county website
Neighborhood: 21401
Nearby schools
GreatSchools rating
- 5/10Annapolis Elementary SchoolGrades: PK-5Distance: 0.2 mi
- 5/10Wiley H. Bates Middle SchoolGrades: 6-8Distance: 0.8 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 4 mi
Schools provided by the listing agent
- 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
$1,448,600
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Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,448,600
- Maryland
- Anne Arundel County
- Annapolis
- 21401
- 144 Charles St
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