105 Sheaffer Rd, Chestertown, MD 21620
Property image
Property image
OFF MARKET

105 Sheaffer Rd
Chestertown, MD 21620

  • 4 Beds
  • 2.5 Baths
  • 1,784 sqft (on 1.03 acres)

$441,200

Trulia Estimate
as of Jul 31, 2026

$441,200

Trulia Estimate
as of Jul 31, 2026
4 Beds
2.5 Baths
1,784 sqft
(on 1.03 acres)

Local Information

  • Map ViewExplore the area around 105 Sheaffer 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
2015
Lot Size
1.03 acres
Living Area
1,784 sqft
Price/Sqft
$247
Parking
Garage

About this House

Situated in The Grove", a spectacular community, this 4 bedroom farmhouse has an open floor plan that adds to the relaxed atmosphere of the home. The kitchen has stainless-steel appliances and a soapstone countertop. NEST thermostats keep the indoors comfy, and the utility bills reasonable. The crawl space underneath the house is encapsulated, the walls are insulated, and there is a dehumidifier to keep things dry. Outside you can enjoy a patio that can be used to view over an acre of rolling lawn, along with a picturesque 12' x 24' shed. If the shed space isn't enough, there is an attached 2 car garage to store everything from riding mowers, to toys, or even cars.
105 Sheaffer Rd, Chestertown, MD 21620 is a 4 bedroom, 3 bathroom, 1,784 sqft single-family home built in 2015. It last sold for $351,000 on Mar 22, 2021. It is currently off market. The Trulia Estimate is $441,200, with a rent estimate of $2,860/month.

Home Details for 105 Sheaffer Rd

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Vinyl
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 1.03 acres

Price History for 105 Sheaffer Rd

DatePriceEventSource
03/16/2023ListingRemovedBright MLS #MDQA146472
03/22/2021$351,000Sold
N/A
03/08/2021$330,000PendingBright MLS #MDQA146472
02/10/2021ListingRemovedLocal MLS
01/26/2021$330,000ContingentBright MLS #MDQA146472
01/22/2021$330,000Listed For SaleBright MLS #MDQA146472
10/24/2019$298,000Sold
N/A
08/09/2019$295,000PendingAgent Provided
07/30/2019$295,000PriceChange
Agent Provided
07/29/2019$305,000PriceChange
Agent Provided
07/18/2019$329,000PriceChange
Agent Provided
07/10/2019$349,000Listed For SaleAgent Provided
06/18/2015$271,300Sold
N/A
03/28/2015$268,900PendingAgent Provided
02/11/2015$268,900Listed For SaleAgent Provided
07/07/2014$40,000Sold
N/A
03/06/2014$54,900PendingAgent Provided
01/19/2013$54,900PriceChange
Agent Provided
01/04/2013$60,000PendingToActiveAgent Provided
11/25/2012$60,000PendingAgent Provided
08/30/2012$60,000Listed For SaleAgent Provided

Market trends in Chestertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM
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Property Tax and Assessment

Year2025
Tax$3,252
Assessment$338,900
Home facts updated by county records

Comparable Sales for 105 Sheaffer Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
136 Hilltop Dr, Chestertown, MD
0.24
Single-Family Home
$376,000
05/19/26
3
2
1,432
118 Grant Ct, Chestertown, MD
0.37
Single-Family Home
$460,000
06/29/26
3
2
1,664
216 Blakefield Dr, Chestertown, MD
0.51
Single-Family Home
$552,000
04/17/26
4
3
2,400
206 Flyway Ln, Chestertown, MD
0.41
Single-Family Home
$512,500
04/08/26
4
3.5
3,000
247 Blakefield Dr, Chestertown, MD
0.66
Single-Family Home
$435,000
12/16/25
3
3
2,500
107 Dutchess Rd, Chestertown, MD
1.68
Single-Family Home
$290,000
08/13/25
3
2
1,380
114 Ryan Ct, Chestertown, MD
1.91
Single-Family Home
$355,000
08/12/25
2
2
1,496
215 Fairview Dr, Chestertown, MD
1.96
Single-Family Home
$435,000
07/16/26
3
2.5
1,784
119 Darden Rd, Chestertown, MD
1.71
Single-Family Home
$270,000
03/18/26
3
2
1,424
105 Parma Rd, Chestertown, MD
1.76
Single-Family Home
$322,000
11/14/25
3
2
1,232

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Assigned Schools

These are the assigned schools for 105 Sheaffer Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Homes for sale near 105 Sheaffer Rd

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Off Market Homes Near 105 Sheaffer Rd

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