108 Pine Chip Rd, Chestertown, MD 21620
OFF MARKET

$264,700

Trulia Estimate
  • Studio
  • 1 Bath
  • 1,054 sqft (on 0.46 acres)

108 Pine Chip Rd, Chestertown, MD 21620

Est. Refi. Payment $1,592/mo*
Refinance Your Home
Currently Off Market - Sold Mar 5, 1986 for $15,000

Home Value

Trulia Estimate
$265K
Since last month
Decreased$12K (-4.3%)
Since last year
Decreased$7K (-2.6%)
Since last sale
Increased$248K (+1,656%)
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 +66% in the last 10 years
MonthEstimated value
2026
August 2026$263K
August 2026$263K
July 2026$275K
June 2026$278K
May 2026$276K
April 2026$274K
March 2026$282K
February 2026$269K
January 2026$268K
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
200 Fey Rd, Chestertown, MD
0.08
Single-Family Home
$375,000
10/10/25
3
2
1,572
225 Duke Of Kent St, Chestertown, MD
0.13
Single-Family Home
$395,000
11/10/25
3
2.5
1,850
221 Old Bridge Rd, Chestertown, MD
0.32
Single-Family Home
$359,900
11/24/25
3
2
1,851
209 Rivershore Rd, Chestertown, MD
0.15
Single-Family Home
$790,000
09/23/25
2
1.5
1,401
154 Longfellow Dr, Chestertown, MD
0.81
Single-Family Home
$300,000
05/27/26
3
1
1,408
513 Round Top Rd, Chestertown, MD
0.95
Single-Family Home
$220,000
04/14/26
4
1
1,248
211 Richard Dr, Chestertown, MD
0.65
Single-Family Home
$327,500
03/04/26
3
2
1,598
517 Round Top Rd, Chestertown, MD
0.97
Single-Family Home
$289,000
08/21/26
3
1
1,248
521 N Kent St, Chestertown, MD
0.68
Single-Family Home
$365,000
07/22/26
3
2
1,934
200 David Dr, Chestertown, MD
0.74
Single-Family Home
$390,000
10/28/25
2
1,885

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
112 Pine Chip Rd, Chestertown, MD 21620
0.02
$346,100
3
1
1,248
Off Market
200 Fey Rd, Chestertown, MD 21620
0.08
$391,700
3
2
1,572
Off Market
249 Duke Of Kent St, Chestertown, MD 21620
0.14
$149,500
3
2
1,556
Off Market
241 Duke Of Kent St, Chestertown, MD 21620
0.12
$394,700
3
2
1,494
Off Market
225 Duke Of Kent St, Chestertown, MD 21620
0.13
$395,000
3
2.5
1,850
Recently Sold
312 Princess Anne Dr, Chestertown, MD 21620
0.18
$466,900
4
2.5
1,848
Off Market
209 Rivershore Rd, Chestertown, MD 21620
0.15
$826,500
2
1.5
1,401
Off Market
209 Princess Anne Dr, Chestertown, MD 21620
0.20
$425,800
3
2
1,776
Off Market
216 Princess Anne Dr, Chestertown, MD 21620
0.24
$426,100
3
2
1,568
Off Market
101 Rivershore Rd, Chestertown, MD 21620
0.23
$1,133,900
3
2
1,968
Off Market
201 Princess Anne Dr, Chestertown, MD 21620
0.24
$415,600
3
2
2,092
Off Market
East St, Chestertown, MD 21620
0.23
$75,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 108 Pine Chip 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
1970
Lot Size
0.46 acres
Living Area
1,054 sqft
Price/Sqft
$251

About this House

This single-family home is located at 108 Pine Chip Rd, Chestertown, MD. 108 Pine Chip Rd is in Chestertown, MD and in ZIP code 21620. This property has 1 bathroom and approximately 1,054 sqft of floor space. This property has a lot size of 0.46 acres and was built in 1970.
108 Pine Chip Rd, Chestertown, MD 21620 is a studio, 1 bathroom, 1,054 sqft single-family home built in 1970. It last sold for $15,000 on Mar 5, 1986. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $264,700, with a rent estimate of $1,898/month.

Home Details for 108 Pine Chip Rd

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 1
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Mar 5, 1986
Source: N/A
Sold
$15,000

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 108 Pine Chip Rd

  • What is 108 Pine Chip Rd estimated to be worth?
    Trulia's estimated value for 108 Pine Chip Rd in Chestertown, MD is $264,700.
  • What is the price history for 108 Pine Chip Rd?
    108 Pine Chip Rd in Chestertown, MD last sold for $15,000 in March 1986.
  • 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 108 Pine Chip Rd?
    The lot at 108 Pine Chip Rd in Chestertown, MD is about 0.46 acres (20,020 sq ft).

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