109 Sheaffer Rd, Chestertown, MD 21620
OFF MARKET

$567,700

Trulia Estimate
  • Studio
  • 2 Baths
  • 2,630 sqft (on 1.03 acres)

109 Sheaffer Rd, Chestertown, MD 21620

Est. Refi. Payment $3,341/mo*
Refinance Your Home
Currently Off Market - Sold Oct 1, 1999 for $32,000

Home Value

Trulia Estimate
$568K
Since last month
Increased$11K (+2%)
Since last year
Decreased$12K (-2%)
Since last sale
Increased$536K (+1,675%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$568K
August 2026$568K
July 2026$557K
June 2026$577K
May 2026$571K
April 2026$571K
March 2026$570K
February 2026$560K
January 2026$563K
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
136 Hilltop Dr, Chestertown, MD
0.21
Single-Family Home
$376,000
05/19/26
3
2
1,432
118 Grant Ct, Chestertown, MD
0.38
Single-Family Home
$460,000
06/29/26
3
2
1,664
206 Flyway Ln, Chestertown, MD
0.37
Single-Family Home
$512,500
04/08/26
4
3.5
3,000
216 Blakefield Dr, Chestertown, MD
0.53
Single-Family Home
$552,000
04/17/26
4
3
2,400
247 Blakefield Dr, Chestertown, MD
0.68
Single-Family Home
$435,000
12/16/25
3
3
2,500
307 Rosin Dr, Chestertown, MD
1.77
Single-Family Home
$150,000
03/18/26
3
3
2,816
221 Dutchess Rd, Chestertown, MD
1.80
Single-Family Home
$228,000
07/13/26
3
1.5
2,260
119 Darden Rd, Chestertown, MD
1.70
Single-Family Home
$270,000
03/18/26
3
2
1,424
302 Rosin Dr, Chestertown, MD
1.77
Single-Family Home
$550,000
12/05/25
5
4
3,877
128 Edmore Rd, Chestertown, MD
1.86
Single-Family Home
$392,500
10/30/25
4
2
2,568

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 Sheaffer Rd, Chestertown, MD 21620
0.07
$524,700
4
2.5
2,864
Off Market
317 Union Church Rd, Chestertown, MD 21620
0.14
$730,200
4
3.5
2,512
Off Market
130 Sheaffer Rd, Chestertown, MD 21620
0.20
$457,900
4
2
1,766
Off Market
136 Hilltop Dr, Chestertown, MD 21620
0.21
$376,000
3
2
1,432
Recently Sold
126 Hilltop Dr, Chestertown, MD 21620
0.27
$520,700
3
2.5
2,733
Off Market
209 Myers Rd, Chestertown, MD 21620
0.32
$448,000
3
2
1,846
Off Market
118 Grant Ct, Chestertown, MD 21620
0.38
$460,000
3
2
1,664
Recently Sold
206 Flyway Ln, Chestertown, MD 21620
0.37
$512,500
4
3.5
3,000
Recently Sold
109 Grant Ct, Chestertown, MD 21620
0.43
$417,900
3
2
1,344
Off Market
148 Grant Ct, Chestertown, MD 21620
0.49
$463,700
3
2
1,664
Off Market
216 Blakefield Dr, Chestertown, MD 21620
0.53
$552,000
4
3
2,400
Recently Sold
209 Blakefield Dr, Chestertown, MD 21620
0.55
$441,200
3
2
-
Off Market

Local Information

  • Map ViewExplore the area around 109 Sheaffer Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2000
1.03 acre lot
2,630 sqft
$216/sqft
Garage

About this House

This single-family home is located at 109 Sheaffer Rd, Chestertown, MD. 109 Sheaffer Rd is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 2,630 sqft of floor space. This property has a lot size of 1.03 acres and was built in 2000.
109 Sheaffer Rd, Chestertown, MD 21620 is a studio, 2 bathroom, 2,630 sqft single-family home built in 2000. It last sold for $32,000 on Oct 1, 1999. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $567,700, with a rent estimate of $3,298/month.

Home Details for 109 Sheaffer Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 1.03 acres

Price and Tax history

DateEventPrice
Oct 1, 1999
Source: N/A
Sold
$32,000

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 109 Sheaffer Rd

  • What is 109 Sheaffer Rd estimated to be worth?
    Trulia's estimated value for 109 Sheaffer Rd in Chestertown, MD is $567,700.
  • What is the price history for 109 Sheaffer Rd?
    109 Sheaffer Rd in Chestertown, MD last sold for $32,000 in October 1999.
  • 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 109 Sheaffer Rd have a pool?
    Yes, 109 Sheaffer Rd in Chestertown, MD has a pool.
  • How big is the lot at 109 Sheaffer Rd?
    The lot at 109 Sheaffer Rd in Chestertown, MD is about 1 acre.

Explore by feature - Air Conditioning

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 109 Sheaffer Rd

Skip to last item
Skip to first item

Homes for sale near 109 Sheaffer Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item