301 Pine Tree Rd, Chestertown, MD 21620
OFF MARKET

301 Pine Tree Rd
Chestertown, MD 21620

  • Studio
  • 1 Bath
  • 1,208 sqft (on 0.69 acres)

$185,100

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $1,141/mo*
Refinance Your Home

$185,100

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $1,141/mo*
Refinance Your Home
Studio
1 Bath
1,208 sqft
(on 0.69 acres)

Home Value

Trulia Estimate
$185K
Since last month
Decreased$1K (-0.6%)
Since last year
Increased$15K (+8.8%)
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 +32% in the last 10 years
MonthEstimated value
2026
August 2026$185K
July 2026$186K
June 2026$182K
May 2026$180K
April 2026$162K
March 2026$175K
February 2026$158K
January 2026$164K
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
108 Springbrook Ln, Millington, MD
0.20
Single-Family Home
$475,900
04/17/26
3
2
1,677
101 Pine Tree Rd, Chestertown, MD
0.50
Single-Family Home
$480,000
05/04/26
4
2
1,848
105 Pearl Creek Ln, Chestertown, MD
0.41
Single-Family Home
$459,000
03/27/26
3
2.5
1,961
2032 Pondtown Rd, Chestertown, MD
0.71
Single-Family Home
$365,000
05/29/26
3
2
1,120
1904 Pondtown Rd, Chestertown, MD
0.73
Single-Family Home
$247,500
08/10/26
3
1
1,967
2101 Dudley Corners Rd, Crumpton, MD
1.24
Single-Family Home
$250,000
10/30/25
2
1
1,200
102 Pine St, Crumpton, MD
1.38
Single-Family Home
$339,900
08/17/26
3
2
1,250
2010 McGinnes Rd, Chestertown, MD
1.41
Single-Family Home
$354,900
11/10/25
3
1
1,253
2405 McGinnes Rd, Chestertown, MD
0.94
Single-Family Home
$3,319,000
02/06/26
2
1,428
1517 Dudley Corners Rd, Millington, MD
0.77
Single-Family Home
$220,000
05/18/26
6
3
2,948

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
305 Pine Tree Rd, Chestertown, MD 21620
0.03
$272,500
2
1
826
Off Market
206 Springbrook Ln, Millington, MD 21651
0.16
$449,600
3
2
1,680
Off Market
200 Ashley Ln, Chestertown, MD 21620
0.19
$475,400
3
1.5
1,656
Off Market
108 Springbrook Ln, Millington, MD 21651
0.20
$475,900
3
2
1,677
Recently Sold
340 Pine Tree Rd, Chestertown, MD 21620
0.26
$248,400
Studio
-
1,080
Off Market
204 Spring Rd, Millington, MD 21651
0.31
$190,500
Studio
1
759
Off Market
Par 113 Spring Rd, Millington, MD 21651
0.33
-
-
-
-
Off Market
136 Pearl Creek Ln, Chestertown, MD 21620
0.36
-
3
2.5
1,460
Off Market
105 Pearl Creek Ln, Chestertown, MD 21620
0.41
$459,000
3
2.5
1,961
Recently Sold
224 Spring Rd, Millington, MD 21651
0.43
-
-
-
-
Off Market
112 Pine Tree Rd, Chestertown, MD 21620
0.46
-
-
-
-
Off Market
101 Pine Tree Rd, Chestertown, MD 21620
0.50
$480,000
4
2
1,848
Recently Sold

Local Information

  • Map ViewExplore the area around 301 Pine Tree Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Lot Size
0.69 acres
Living Area
1,208 sqft
Price/Sqft
$153
Parking
Garage

About this House

This single-family home is located at 301 Pine Tree Rd, Chestertown, MD. 301 Pine Tree Rd is in Chestertown, MD and in ZIP code 21620. This property has 1 bathroom and approximately 1,208 sqft of floor space. This property has a lot size of 0.69 acres and was built in 1950.
301 Pine Tree Rd, Chestertown, MD 21620 is a studio, 1 bathroom, 1,208 sqft single-family home built in 1950. It is currently off market. The Trulia Estimate is $185,100, with a rent estimate of $1,852/month.

Home Details for 301 Pine Tree Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price and Tax history

YearProperty taxTax assessment
2025
$1,754
$179,800
Home facts updated by county records

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 301 Pine Tree Rd

  • What is 301 Pine Tree Rd estimated to be worth?
    Trulia's estimated value for 301 Pine Tree Rd in Chestertown, MD is $185,100.
  • 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.
  • What are the closest schools to 301 Pine Tree Rd?
    The closest schools to 301 Pine Tree Rd in Chestertown, MD are Queen Anne's County High School (rated 7/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).
  • How big is the lot at 301 Pine Tree Rd?
    The lot at 301 Pine Tree Rd in Chestertown, MD is about 0.69 acres (30,056 sq ft).
  • Does 301 Pine Tree Rd have a garage?
    Yes, 301 Pine Tree Rd in Chestertown, MD has a garage.

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