144 Charles St, Annapolis, MD 21401
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Property image
OFF MARKET

144 Charles St
Annapolis, MD 21401

  • 4 Beds
  • 3.5 Baths
  • 2,089 sqft

$1,448,600

Trulia Estimate
as of Jul 29, 2026

$1,448,600

Trulia Estimate
as of Jul 29, 2026
4 Beds
3.5 Baths
2,089 sqft

Local Information

  • Map ViewExplore the area around 144 Charles St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Living Area
2,089 sqft
Price/Sqft
$693
Parking
Open Parking

About this House

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.
144 Charles St, Annapolis, MD 21401 is a 4 bedroom, 4 bathroom, 2,089 sqft single-family home built in 1900. It last sold for $1,425,000 on Apr 29, 2025 (6% above the $1,350,000 asking price). It is currently off market. The Trulia Estimate is $1,448,600, with a rent estimate of $4,578/month.

Home Details for 144 Charles St

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 13Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Basement, Dining Room, Family Room, Kitchen, Laundry
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2089 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Natural Gas Available, Sewer Available, Water AvailableAppliances: Disposal, Dryer, Oven/Range - Gas, Refrigerator, Washer, Dishwasher, Gas Water HeaterDishwasherDisposalDryerLaundry: Upper Level,Washer In Unit,Dryer In Unit,Has Laundry,Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Radiator,Natural GasHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Radiator
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Wood FramesDoor: French DoorsFlooring: Hardwood, Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Hardwood, Ceramic Tile, Wood
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: Deck, PatioOther Structures: Above Grade, Below GradeExterior: Extensive Hardscape, LightingNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: On Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2089 Square Feet

Property Information

Year Built
Year Built: 1900Year Renovated: 2023
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Twin/Semi-DetachedArchitecture: Traditional
Building
Construction Materials: Other, Wood SidingNot a New ConstructionAttached To Another Structure
Property Information
Condition: ExcellentIncluded in Sale: Sonos Sound System, Wall Mounted Tvs, Security SystemParcel Number: 020600002422507

Price & Status

Price
List Price: $1,350,000
Status Change & Dates
Off Market Date: Tue Apr 29 2025Possession Timing: Seller Rent Back, Negotiable, Close Of Escrow

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: ANNAPOLISCommunity: Historic District
School Information
Elementary School District: Anne Arundel County Public SchoolsJr High / Middle School District: Anne Arundel County Public SchoolsHigh School District: Anne Arundel County Public Schools

Building

Building Area
Building Area: 2689 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1980 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2106388Municipality: AnnapolisAbove Grade Unfinished Area: 2089
Last check for updates: 37 minutes ago
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, (443) 685-4043, Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS, MLS#MDAA2106388

Price History for 144 Charles St

DatePriceEventSource
04/29/2025$1,425,000Sold
Bright MLS #MDAA2106388
04/10/2025$1,350,000PendingBright MLS #MDAA2106388
04/04/2025$1,350,000Listed For SaleBright MLS #MDAA2106388
12/07/2020$819,093Sold
N/A
06/24/2020$819,093Sold
N/A
05/27/2020$839,000PendingAgent Provided
02/26/2020$839,000Listed For SaleAgent Provided
03/25/2015$700,000Sold
N/A
01/30/2015$719,900PendingAgent Provided
10/08/2014$719,900Listed For SaleAgent Provided
06/28/2011$639,000Sold
N/A
06/08/2011$689,900Listed For SaleAgent Provided
04/29/2011$689,900ListingRemovedAgent Provided
03/15/2011$689,900Listed For SaleAgent Provided
12/04/2010$699,900ListingRemovedAgent Provided
10/30/2010$699,900PriceChange
Agent Provided
10/10/2010$699,890PriceChange
Agent Provided
09/08/2010$699,900PriceChange
Agent Provided
08/27/2010$739,900PriceChange
Agent Provided
06/27/2010$779,800PriceChange
Agent Provided
04/08/2010$779,900Listed For SaleAgent Provided
02/26/1999$325,000Sold
N/A

Market trends in Annapolis

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$632K
$6.37KMoM
Sale-to-List Price
100.0%
Price per sq ft
$319
$6MoM
Available listings
357
21MoM
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Property Tax and Assessment

Year2025
Tax$12,431
Assessment$867,467
Home facts updated by county records

Comparable Sales for 144 Charles St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
90 Charles St, Annapolis, MD
0.11
Single-Family Home
$1,050,000
06/17/26
3
2.5
1,950
146 Duke Of Gloucester St, Annapolis, MD
0.13
Single-Family Home
$1,399,900
09/29/25
4
3.5
3,042
146 Prince George St, Annapolis, MD
0.28
Single-Family Home
$1,650,000
10/14/25
4
2.5
2,550
60 Cornhill St, Annapolis, MD
0.14
Single-Family Home
$1,650,000
07/30/25
3
3.5
1,806
168 Green St, Annapolis, MD
0.16
Single-Family Home
$1,098,000
01/05/26
3
2.5
1,922
163 Prince George St, Annapolis, MD
0.25
Single-Family Home
$1,325,000
05/27/26
3
2.5
2,434
199 Prince George St, Annapolis, MD
0.23
Single-Family Home
$834,750
10/29/25
3
3
1,770
254 King George St, Annapolis, MD
0.35
Single-Family Home
$1,930,000
07/09/26
4
3
2,877
115 Charles St, Annapolis, MD
0.07
Single-Family Home
$830,000
11/10/25
3
1.5
1,491

Nearby homes

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Assigned Schools

These are the assigned schools for 144 Charles St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Annapolis

At least 470 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 83 % Say car is needed

  • 75 % Say there's holiday spirit

  • 73 % Say parking is easy

  • 73 % Say there are sidewalks

  • 70 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 68 % Say kids play outside

  • 66 % Say streets are well-lit

  • 65 % Say it's quiet

  • 63 % Say there's wildlife

  • 57 % Say it's walkable to restaurants

  • 57 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Shannon Chatlos
    "If you like coastal living and a laid-back lifestyle, and are willing to pay for it, this a wonderful place to live."
    0
    Flag
  • Sylvie Bracke
    "It’s a very dog friendly place - I just can’t help wondering why some people don’t clean up after their pets? It’s a nice neighborhood with high end properties & I don’t get that dissonance."
    0
    Flag
  • Erin
    "Safe. On water. Paths in woods. Friendly. Dog play area. Lots of open spaces. Areas are walkable, clean. "
    0
    Flag
  • Halljanie68
    "Community Pool convenient shopping. Easy access to major routes 50/95 Easy access to downtown Annapolis "
    0
    Flag
  • Sheila Wilson
    "A lot of traffic on forest drive very hard to come onto the street. It need a red light or stop sign. Before a serious accident happens. People speed over 40mph"
    0
    Flag
  • Diana H.
    "I’m not sure, I don’t own a dog. Plenty walk by my dead end street house daily though and the neighborhood seems safe for both dogs and owners. "
    0
    Flag
  • Paul Eric Watson
    "Love the urban feel. Lots of history and near the water is a bonus. Very walkable and always something going on. "
    5
    Flag
  • Trulia User
    "Access to Route 50, the Bay Bridge, and Sandy Point State Park. Thirty minutes to Baltimore. Forty minutes to Washington D.C."
    2
    Flag
  • Trulia User
    "It’s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "It’s a tad busy commute rush hour traffic is something to consider small town lots of people takes about 10-15 min or so to get from one side of town to the other without traffic "
    1
    Flag
  • Trulia User
    "Great school public and private well maintained parks great public libraries close downtown Annapolis shopping for everything is conveniently close "
    0
    Flag
  • Trulia User
    "Lots of families with dogs. Poop bag stations throughout the neighborhood. Lots of woods to walk thru and sidewalks too. "
    1
    Flag
  • Trulia User
    "Nothing is special about my neighborhood. So quiet and nobody talks to anybody. The play area was demolished so no kids can hang out to play."
    4
    Flag
  • Trulia User
    "This is an excellent neighborhood for families and the neighbors are wonderful. Cape St. John gives you access to everything in Annapolis with the tranquility of living along the river."
    0
    Flag
  • Trulia User
    "While Truxton is dog friendly it would be nice to have a dedicated dog park closer than Quiet Waters. "
    0
    Flag
  • Trulia User
    "Wonderful family neighborhood. This neighborhood is very convenient to Hway 50 and all of the Annapolis area. The people here are terrific neighbors."
    0
    Flag
  • Trulia User
    "Good to walk. And parks are nice to play with kids. Stores are close by. And dog walkers all around. "
    0
    Flag
  • Trulia User
    "Summer beach parties, puppy happy hours, annual sock burning, lots of parks and the people are wonderful!"
    0
    Flag
  • Trulia User
    "the history Open napolis is amazing the people around here are kind and friendly and the schools are phenomenal"
    0
    Flag
  • Singletonad
    "the public school system in Annapolis needs to get significantly stronger overall. The private school system here is quite reliable."
    0
    Flag
  • Keren_molina
    "Lovely place and definitely good place to live and have a dog and a lot sores to go buy stuff ..........."
    5
    Flag
  • Singletonad
    "There is no community dog run here and no sidewalks so it can feel awkward letting your dog poop in someone else's yard even if you pick it up. The vast majority of neighbors are dog friendly, but not all, and that is their perogative."
    0
    Flag
  • Bgonos7
    "A lot of space to walk and nearby parks. Nice area and everyone is dog friendly for the most part. A lot of Neighbors have dogs "
    0
    Flag
  • Raddisob07
    " N/A school are great parking is great close to everything ppl are friendly and been living in Annapolis all my life "
    4
    Flag
  • Tery_hodges
    "I walk my son to elementary school. We can walk to many restaurants and “tourist” shops but do have to drive to get to a grocery store."
    2
    Flag
  • Stephanie.ward0715
    "I've been around this area for years. People are friendly and always willing to help each other. The restaurant's and shopping are also a plus. Everything you are looking for is 5 minutes away."
    0
    Flag
  • Raddisob07
    "None that I know of. The community should definitely do more collaborative events at least at least Quarterly they are family friendly."
    5
    Flag
  • Stella
    "Feel good living here Parking so easy Location very good Many things nearby Old town and new town "
    3
    Flag
  • Jennifer B.
    "It's super quiet and funny, I've leving here for 1 year and I feel safe my neighbors are nice.. Down town is amazing.. ❤️ "
    0
    Flag
  • Kwisniewski805
    "Holiday events and many boating events. There are street fairs, food markets, holiday markets. Community is very close. "
    0
    Flag
  • Cara M. E.
    "I teach at a school that is less than 10 minutes from my house. But there are times that Forest Dr gets incredibly backed up, or there is an accident that causes the road to be shut down. "
    1
    Flag
  • Beth S.
    "Bad area is close by, so kids need to understand boundaries. Private schools are important here, so save your money. Sports are good here, with lots of good coaching."
    0
    Flag
  • Linda D.
    "I've been visiting a dear close friend - helping them recuperate from serious surgery. traffic is atrocious- I miss living in the rural countryside area!"
    0
    Flag
  • Liza
    "The schools in Annapolis are not as good as they are in Severna Park which is where I grew up originally. But Annapolis has many great amenities including local places to eat and shop."
    0
    Flag
  • Rodwellsantos6
    "I like it this community is pretty good as so matters fact for elders we looking to buy in this areas I don’t know frankly about this gorgeous homes we will see."
    0
    Flag
  • Jeffrey H.
    "Lived here for 4 years. Loved the area, including the park across the street. Hate the maintenance of the building including the attention to detail of maintenance of property. "
    0
    Flag
  • jfh4k0
    "Local traffic is not too bad. Beach traffic and rush hour traffic to DC and Baltimore is pretty terrible. "
    2
    Flag
  • Nadja Maril
    "I lived in this neighborhood over 20 years and walk downtown with my dog every morning for coffee. On pretty days we visit City Dock and admire the views and the boats."
    1
    Flag
  • Markkimethanmolly
    "We’ve lived here for 18 years, and everyone is very friendly. Our neighborhood is very safe and quiet."
    0
    Flag
  • Debwill64
    "There is a bus stop close enough to walk to but I have to drive to DC. The bus only goes to Annapolis and maybe Baltimore, not sure though."
    0
    Flag

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Homes for sale near 144 Charles St

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Off Market Homes Near 144 Charles St

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information