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

$1,450,800

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,089 sqft

144 Charles St, Annapolis, MD 21401

Refinance Your Home
Currently Off Market - Sold Apr 29, 2025 for $1,425,000

Home Value

Trulia Estimate
$1.45M
Since last month
Decreased$9K (-0.6%)
Since last year
Increased$37K (+2.6%)
Since last sale
Increased$27K (+1.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +104% in the last 10 years
MonthEstimated value
2026
August 2026$1.45M
August 2026$1.45M
July 2026$1.46M
June 2026$1.45M
May 2026$1.44M
April 2026$1.44M
March 2026$1.44M
February 2026$1.43M
January 2026$1.41M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
12 Union St, Annapolis, MD
0.10
Single-Family Home
$1,260,000
09/10/26
4
2
2,265
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 home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
142 Charles St, Annapolis, MD 21401
0.00
$1,570,700
5
2.5
2,914
Off Market
140 Charles St, Annapolis, MD 21401
0.01
$1,206,300
3
2.5
1,635
Off Market
138 Charles St, Annapolis, MD 21401
0.02
$1,418,800
4
3
3,100
Off Market
192 Duke Of Gloucester St, Annapolis, MD 21401
0.03
$1,950,000
6
4
3,415
For Sale
196 Duke Of Gloucester St, Annapolis, MD 21401
0.03
$1,991,200
4
3.5
2,288
Off Market
3413 Halifax Ct, Pasadena, MD 21122
0.07
$449,000
3
2.5
1,800
For Sale
11705 Cheviot Ct, Upper Marlboro, MD 20772
0.07
$499,900
5
3
2,888
For Sale
8904 Ballard Ln, Clinton, MD 20735
0.07
$579,000
4
3
2,250
For Sale
8227 White Star Xing, Pasadena, MD 21122
0.07
$485,000
3
2.5
2,332
For Sale
510 Wilson Bridge Dr #6711-C-1, Oxon Hill, MD 20745
0.07
$99,900
1
1
684
For Sale
1118 Spalding Dr #33, Bel Air, MD 21014
0.07
$285,000
2
2
1,330
For Sale

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

Single-Family Home
Built in 1900
2,089 sqft
$694/sqft
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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,450,800, with a rent estimate of $4,694/month.
Last check for updates: about 5 hours 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

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

Price and Tax history

DateEventPrice
Apr 29, 2025
Source: Bright MLS #MDAA2106388
Sold
$1,425,000
Apr 10, 2025
Source: Bright MLS #MDAA2106388
Pending
$1,350,000
Apr 4, 2025
Source: Bright MLS #MDAA2106388
Listed For Sale
$1,350,000
Dec 7, 2020
Source: N/A
Sold
$819,093
Jun 24, 2020
Source: N/A
Sold
$819,093

Market trends in Annapolis

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$643K
$1KMoM
Sale-to-List Price
100.0%
Price per sq ft
$331
$6MoM
Available listings
344
11MoM

Around this home

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.
  • Trulia User
    "Very dog friendly neighborhood. But not a lot of green space other than other peoples’ yards. "
    0
    Flag
  • 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
  • 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
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  • 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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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

Frequently asked questions about 144 Charles St

  • What is 144 Charles St estimated to be worth?
    Trulia's estimated value for 144 Charles St in Annapolis, MD is $1,450,800.
  • What is the price history for 144 Charles St?
    144 Charles St in Annapolis, MD last sold for $1,425,000 in April 2025.
  • Is Annapolis a buyer's or seller's market?
    Annapolis is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Annapolis?
    The median sale price in Annapolis is $643K. That is down $1K from the prior month.
  • Does 144 Charles St have air conditioning?
    Yes, 144 Charles St in Annapolis, MD has air conditioning.
  • Does 144 Charles St have laundry facilities?
    Yes, 144 Charles St in Annapolis, MD has in-unit laundry.

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