159 Flatland Rd, Chestertown, MD 21620
OFF MARKET

$334,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,344 sqft (on 1.77 acres)

159 Flatland Rd, Chestertown, MD 21620

Est. Refi. Payment $1,990/mo*
Refinance Your Home
Currently Off Market - Sold Jan 8, 2025 for $220,000

Home Value

Trulia Estimate
$334K
Since last month
Increased$600 (+0.2%)
Since last year
Increased$41K (+13.9%)
Since last sale
Increased$116K (+52.8%)
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 +172% in the last 10 years
MonthEstimated value
2026
August 2026$336K
August 2026$334K
July 2026$336K
June 2026$344K
May 2026$340K
April 2026$335K
March 2026$328K
February 2026$326K
January 2026$320K
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
318 Lincoln Dr, Chestertown, MD
0.17
Single-Family Home
$255,000
01/16/26
3
2
960
301 Lincoln Dr, Chestertown, MD
0.25
Single-Family Home
$293,000
06/08/26
3
2
1,152
8629 Airy Hill Rd, Chestertown, MD
0.62
Single-Family Home
$395,000
06/25/26
3
2
1,440
107 Malone Ave, Chestertown, MD
0.70
Single-Family Home
$290,000
01/16/26
3
1
1,200
304 Hadaway Dr, Chestertown, MD
1.04
Single-Family Home
$300,000
07/30/26
4
2
1,325
8978 Orchard Dr, Chestertown, MD
0.80
Single-Family Home
$680,000
09/30/25
4
2.5
3,820
139 Prospect St, Chestertown, MD
0.87
Single-Family Home
$195,000
07/31/26
3
1
1,200
141 Prospect St, Chestertown, MD
0.86
Single-Family Home
$120,000
02/27/26
4
1.5
1,156
144 Prospect St, Chestertown, MD
0.85
Single-Family Home
$165,000
07/07/26
2
1.5
1,082
126 Metcalf Rd, Chestertown, MD
1.09
Single-Family Home
$230,000
11/20/25
3
2
1,140

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 Roosevelt Dr, Chestertown, MD 21620
0.10
$60,000
-
-
-
For Sale
306 Roosevelt Dr, Chestertown, MD 21620
0.14
$291,100
3
1.5
1,152
Off Market
318 Lincoln Dr, Chestertown, MD 21620
0.17
$255,000
3
2
960
Recently Sold
300 Hilltop Ln, Chestertown, MD 21620
0.18
$221,100
3
2.5
1,200
Off Market
104 Lincoln Dr, Chestertown, MD 21620
0.18
$300,000
3
1
960
For Sale
304 Hilltop Ln, Chestertown, MD 21620
0.18
$216,100
3
2.5
1,199
Off Market
316 Roosevelt Dr, Chestertown, MD 21620
0.18
$311,300
3
2
1,200
Off Market
310 Hilltop Ln, Chestertown, MD 21620
0.18
$205,700
3
2.5
1,216
Off Market
305 Lincoln Dr, Chestertown, MD 21620
0.25
$311,100
4
2.5
1,632
Off Market
301 Lincoln Dr, Chestertown, MD 21620
0.25
$293,000
3
2
1,152
Recently Sold
114 Metcalf Rd, Chestertown, MD 21620
0.28
$244,900
3
1.5
-
Off Market
118 Metcalf Rd, Chestertown, MD 21620
0.28
$258,900
3
1.5
1,140
Off Market

Local Information

  • Map ViewExplore the area around 159 Flatland Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1955
Lot Size
1.77 acres
Living Area
1,344 sqft
Price/Sqft
$249
Parking
Garage

About this House

Chestertown rancher with attached garage on 1.7 acres. Two levels, walk-out basement and workshop area, with overhead door. In Town limits.
159 Flatland Rd, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 1,344 sqft single-family home built in 1955. It last sold for $220,000 on Jan 8, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $334,100, with a rent estimate of $2,000/month.

Home Details for 159 Flatland Rd

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

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: 1.77 acres

Price and Tax history

DateEventPrice
Jan 8, 2025
Source: N/A
Sold
$220,000
Jan 17, 2018
Source: Agent Provided
ListingRemoved
$119,900
Sep 14, 2017
Source: Agent Provided
PriceChange
$119,900
Price decreased by 8%
Aug 25, 2016
Source: Agent Provided
Listed For Sale
$129,900
Nov 16, 2011
Source: Agent Provided
ListingRemoved
$295,000

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 159 Flatland Rd

  • What is 159 Flatland Rd estimated to be worth?
    Trulia's estimated value for 159 Flatland Rd in Chestertown, MD is $334,100.
  • What is the price history for 159 Flatland Rd?
    159 Flatland Rd in Chestertown, MD last sold for $220,000 in January 2025.
  • 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 159 Flatland Rd?
    The lot at 159 Flatland Rd in Chestertown, MD is about 1.8 acres.
  • Does 159 Flatland Rd have a garage?
    Yes, 159 Flatland Rd in Chestertown, MD has a garage.

Apartments for Rent

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Off Market Homes Near 159 Flatland Rd

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