
144 Charles St Annapolis, MD 21401
Downtown Annapolis NeighborhoodHighlights
- Gourmet Kitchen
- Traditional Architecture
- No HOA
- Deck
- Solid Hardwood Flooring
- 1-minute walk to Davidsonville Park
About This Home
As of April 2025Timeless 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.
Last Agent to Sell the Property
Coldwell Banker Realty License #634990 Listed on: 04/04/2025

Townhouse Details
Home Type
- Townhome
Est. Annual Taxes
- $11,366
Year Built
- Built in 1900 | Remodeled in 2023
Lot Details
- 1,980 Sq Ft Lot
- West Facing Home
- Extensive Hardscape
- Historic Home
- Property is in excellent condition
Parking
- On-Street Parking
Home Design
- Semi-Detached or Twin Home
- Traditional Architecture
- Wood Siding
Interior Spaces
- Property has 3 Levels
- Built-In Features
- Crown Molding
- Wood Frame Window
- French Doors
- Family Room
- Dining Room
- Unfinished Basement
Kitchen
- Gourmet Kitchen
- Breakfast Area or Nook
- Gas Oven or Range
- Dishwasher
- Upgraded Countertops
- Disposal
Flooring
- Solid Hardwood
- Ceramic Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- En-Suite Primary Bedroom
- En-Suite Bathroom
Laundry
- Laundry Room
- Laundry on upper level
- Dryer
- Washer
Outdoor Features
- Deck
- Patio
- Exterior Lighting
Utilities
- Central Air
- Radiator
- Natural Gas Water Heater
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 020600002422507
Community Details
Overview
- No Home Owners Association
- Historic District Subdivision
Pet Policy
- Pets Allowed
Ownership History
Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Purchase Details
Similar Homes in Annapolis, MD
Home Values in the Area
Average Home Value in this Area
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Deed | $1,425,000 | Allied Title | |
Deed | $1,425,000 | Allied Title | |
Warranty Deed | -- | None Listed On Document | |
Deed | $819,093 | Liberty Title And Escrow Co | |
Deed | $700,000 | First American Title Ins Co | |
Deed | $639,000 | -- | |
Deed | $639,000 | Mid Maryland Title Co Inc | |
Deed | $639,000 | -- | |
Deed | -- | -- | |
Deed | $325,000 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Previous Owner | $560,000 | New Conventional | |
Previous Owner | $280,500 | New Conventional | |
Previous Owner | $310,000 | New Conventional | |
Previous Owner | $310,000 | New Conventional |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
04/29/2025 04/29/25 | Sold | $1,425,000 | +5.6% | $682 / Sq Ft |
04/10/2025 04/10/25 | Pending | -- | -- | -- |
04/04/2025 04/04/25 | For Sale | $1,350,000 | +64.8% | $646 / Sq Ft |
06/26/2020 06/26/20 | Sold | $819,093 | -2.4% | $394 / Sq Ft |
05/27/2020 05/27/20 | Pending | -- | -- | -- |
05/25/2020 05/25/20 | For Sale | $839,000 | +2.4% | $403 / Sq Ft |
03/31/2020 03/31/20 | Off Market | $819,093 | -- | -- |
02/26/2020 02/26/20 | For Sale | $839,000 | +19.9% | $403 / Sq Ft |
03/16/2015 03/16/15 | Sold | $700,000 | -2.8% | $337 / Sq Ft |
01/27/2015 01/27/15 | Pending | -- | -- | -- |
10/07/2014 10/07/14 | For Sale | $719,900 | -- | $346 / Sq Ft |
Tax History Compared to Growth
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $11,366 | $867,467 | -- | -- |
2024 | $11,366 | $790,933 | $0 | $0 |
2023 | $10,259 | $714,400 | $557,100 | $157,300 |
2022 | $10,062 | $714,133 | $0 | $0 |
2021 | $20,117 | $713,867 | $0 | $0 |
2020 | $10,062 | $713,600 | $557,100 | $156,500 |
2019 | $18,503 | $677,233 | $0 | $0 |
2018 | $8,914 | $640,867 | $0 | $0 |
2017 | $7,696 | $604,500 | $0 | $0 |
2016 | -- | $587,933 | $0 | $0 |
2015 | -- | $571,367 | $0 | $0 |
2014 | -- | $554,800 | $0 | $0 |
Agents Affiliated with this Home
-
Seller's Agent in 2025
Kate Hopkins
Coldwell Banker (NRT-Southeast-MidAtlantic)
(410) 703-8502
3 in this area
45 Total Sales
-
Seller Co-Listing Agent in 2025
Liz Montaner
Coldwell Banker (NRT-Southeast-MidAtlantic)
(443) 871-1143
16 in this area
103 Total Sales
-
Buyer's Agent in 2025
Kristen Boyer
BHHS PenFed (actual)
(443) 685-4043
2 in this area
61 Total Sales
-
J
Seller's Agent in 2020
Jenna Smith
Redfin Corp
-
Seller Co-Listing Agent in 2020
Ben Garner
Cummings & Co Realtors
(240) 216-7841
564 Total Sales
-
Buyer's Agent in 2020
HUNTER MESSINEO
Blackwell Real Estate, LLC
(443) 574-7500
16 Total Sales
Map
Source: Bright MLS
MLS Number: MDAA2106388

APN: 06-000-02422507
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