104 Pine St, Chestertown, MD 21620
Property image
Property image
OFF MARKET

$350,000

Trulia Estimate
  • Studio
  • 2 Baths
  • 1,708 sqft (on 0.26 acres)

104 Pine St, Chestertown, MD 21620

Refinance Your Home
Currently Off Market - Sold Mar 22, 2022 for $275,000

Home Value

Trulia Estimate
$350K
Since last month
Decreased$4K (-1.1%)
Since last year
Increased$2K (+0.7%)
Since last sale
Increased$76K (+27.6%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$351K
August 2026$350K
July 2026$355K
June 2026$358K
May 2026$354K
April 2026$354K
March 2026$353K
February 2026$345K
January 2026$344K
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
205 Pine St, Chestertown, MD
0.18
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
304 Hadaway Dr, Chestertown, MD
0.13
Single-Family Home
$300,000
07/30/26
4
2
1,325
112 Elm St, Chestertown, MD
0.09
Single-Family Home
$249,000
06/12/26
3
1
1,356
109 Cedar St, Chestertown, MD
0.18
Single-Family Home
$318,000
08/14/26
3
2
1,397
111 Pine St, Chestertown, MD
0.07
Single-Family Home
$347,000
05/05/26
5
1
1,645
411 Greenwood Ave, Chestertown, MD
0.26
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
202 Pine St, Chestertown, MD
0.16
Single-Family Home
$222,000
09/08/26
3
1
1,341
204 Rolling Rd, Chestertown, MD
0.33
Single-Family Home
$340,000
03/19/26
3
2
2,296
224 Valley Rd, Chestertown, MD
0.31
Single-Family Home
$455,000
10/21/25
3
2
1,886
217 Philosophers Ter, Chestertown, MD
0.51
Single-Family Home
$370,000
05/01/26
3
1.5
1,404

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
106 Pine St, Chestertown, MD 21620
0.01
$299,100
3
1
1,376
Off Market
108 Pine St, Chestertown, MD 21620
0.03
$85,000
3
1
910
Recently Sold
112 Elm St, Chestertown, MD 21620
0.09
$249,000
3
1
1,356
Recently Sold
304 Hadaway Dr, Chestertown, MD 21620
0.13
$300,000
4
2
1,325
Recently Sold
111 Elm St, Chestertown, MD 21620
0.13
$257,200
3
1
1,275
Off Market
118 Elm St, Chestertown, MD 21620
0.13
$447,500
3
2.5
2,008
Off Market
201 Greenwood Ave, Chestertown, MD 21620
0.14
$495,000
4
3
3,984
Recently Sold
202 Pine St, Chestertown, MD 21620
0.16
$222,000
3
1
1,341
Recently Sold
205 Pine St, Chestertown, MD 21620
0.18
$297,900
3
1.5
2,212
Off Market
109 Cedar St, Chestertown, MD 21620
0.18
$318,000
3
2
1,397
Recently Sold
202 Valley Rd, Chestertown, MD 21620
0.26
$325,000
3
1
1,427
Recently Sold
411 Greenwood Ave, Chestertown, MD 21620
0.26
$415,000
3
2.5
1,676
Recently Sold

Local Information

  • Map ViewExplore the area around 104 Pine St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1956
0.26 acre lot
1,708 sqft
$205/sqft

About this House

This single-family home is located at 104 Pine St, Chestertown, MD. 104 Pine St is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 1,708 sqft of floor space. This property has a lot size of 0.26 acres and was built in 1956.
104 Pine St, Chestertown, MD 21620 is a studio, 2 bathroom, 1,708 sqft single-family home built in 1956. It last sold for $275,000 on Mar 22, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $350,000, with a rent estimate of $2,109/month.

Home Details for 104 Pine St

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Dec 5, 2023
Source: Bright MLS #MDKE2000414
ListingRemoved
Mar 22, 2022
Source: N/A
Sold
$275,000
Dec 3, 2021
Source: Bright MLS #MDKE2000414
Sold
$275,000
Sep 13, 2021
Source: Bright MLS #MDKE2000414
Pending
$274,900
Sep 1, 2021
Source: Bright MLS #MDKE2000414
PriceChange
$274,900
Price decreased by 4%

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
5MoM

Around this home

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 104 Pine St

  • What is 104 Pine St estimated to be worth?
    Trulia's estimated value for 104 Pine St in Chestertown, MD is $350,000.
  • What is the price history for 104 Pine St?
    104 Pine St in Chestertown, MD last sold for $275,000 in March 2022.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • How big is the lot at 104 Pine St?
    The lot at 104 Pine St in Chestertown, MD is about 0.26 acres (11,325 sq ft).

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