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

$335,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,616 sqft (on 0.30 acres)

206 Pine St, Chestertown, MD 21620

Refinance Your Home
Currently Off Market - Sold Sep 7, 2021 for $260,000

Home Value

Trulia Estimate
$335K
Since last month
Decreased$3K (-0.9%)
Since last year
Decreased$500 (-0.1%)
Since last sale
Increased$77K (+29.4%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$337K
August 2026$335K
July 2026$340K
June 2026$343K
May 2026$340K
April 2026$340K
March 2026$338K
February 2026$333K
January 2026$330K
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
0.04
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
202 Pine St, Chestertown, MD
0.04
Single-Family Home
$222,000
09/08/26
3
1
1,341
303 E Campus Ave, Chestertown, MD
0.29
Single-Family Home
$364,000
01/16/26
3
2
1,532
224 Valley Rd, Chestertown, MD
0.18
Single-Family Home
$455,000
10/21/25
3
2
1,886
109 Cedar St, Chestertown, MD
0.23
Single-Family Home
$318,000
08/14/26
3
2
1,397
112 Elm St, Chestertown, MD
0.16
Single-Family Home
$249,000
06/12/26
3
1
1,356
204 Rolling Rd, Chestertown, MD
0.27
Single-Family Home
$340,000
03/19/26
3
2
2,296
202 Valley Rd, Chestertown, MD
0.07
Single-Family Home
$325,000
06/17/26
3
1
1,427
411 Greenwood Ave, Chestertown, MD
0.22
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
217 Philosophers Ter, Chestertown, MD
0.31
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
202 Valley Rd, Chestertown, MD 21620
0.07
$325,000
3
1
1,427
Recently Sold
202 Pine St, Chestertown, MD 21620
0.04
$222,000
3
1
1,341
Recently Sold
205 Pine St, Chestertown, MD 21620
0.04
$297,900
3
1.5
2,212
Off Market
206 Valley Rd, Chestertown, MD 21620
0.10
$590,000
4
2
2,869
Recently Sold
201 Greenwood Ave, Chestertown, MD 21620
0.08
$495,000
4
3
3,984
Recently Sold
306 Cedar St, Chestertown, MD 21620
0.13
$312,800
4
2
1,404
Off Market
118 Elm St, Chestertown, MD 21620
0.12
$447,500
3
2.5
2,008
Off Market
303 Cedar St, Chestertown, MD 21620
0.14
$325,000
3
2.5
2,577
Recently Sold
307 Cedar St, Chestertown, MD 21620
0.17
$308,800
3
1
1,472
Off Market
101 School Rd, Chestertown, MD 21620
0.18
$364,200
3
1.5
1,424
Off Market
112 Elm St, Chestertown, MD 21620
0.16
$249,000
3
1
1,356
Recently Sold
224 Valley Rd, Chestertown, MD 21620
0.18
$457,400
3
2
1,886
Off Market

Local Information

  • Map ViewExplore the area around 206 Pine St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
0.3 acre lot
1,616 sqft
$208/sqft

About this House

Beautifully maintained brick home located 1-2 blocks from Washington College. Freshly painted inside with gleaming wood floors throughout most of the house. Kitchen has new vinyl flooring. There is a huge family room addition at the rear of the house. Living room and dining room combine to make for a very spacious living area. Large floored attic. The covered side porch is perfect for relaxing!
206 Pine St, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 1,616 sqft single-family home built in 1955. It last sold for $260,000 on Sep 7, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $335,400, with a rent estimate of $1,892/month.

Home Details for 206 Pine St

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other, Brick

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price and Tax history

DateEventPrice
Sep 7, 2021
Source: Bright MLS #MDKE2000260
Sold
$260,000
Aug 15, 2018
Source: N/A
Sold
$184,500
Jun 24, 2018
Source: Agent Provided
Pending
$184,500
Jun 1, 2018
Source: Agent Provided
Listed For Sale
$184,500
Feb 12, 2003
Source: N/A
Sold
$144,500

Market trends in Chestertown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
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 206 Pine St

  • What is 206 Pine St estimated to be worth?
    Trulia's estimated value for 206 Pine St in Chestertown, MD is $335,400.
  • What is the price history for 206 Pine St?
    206 Pine St in Chestertown, MD last sold for $260,000 in September 2021.
  • 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.
  • Does 206 Pine St have air conditioning?
    Yes, 206 Pine St in Chestertown, MD has air conditioning.
  • Does 206 Pine St have laundry facilities?
    Yes, 206 Pine St in Chestertown, MD has in-unit laundry.

Explore by feature - Air Conditioning

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