Is a car needed in Chestertown, MD?

As of early 2026, 85% of users say car is needed

Does Chestertown, MD show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Is Chestertown, MD dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Would people walk alone at night in Chestertown, MD?

As of early 2026, 77% of users say people would walk alone at night

Is parking easy in Chestertown, MD?

As of early 2026, 77% of users say parking is easy

Are yards well-kept in Chestertown, MD?

As of early 2026, 76% of users say yards are well-kept

Is Chestertown, MD quiet?

As of early 2026, 74% of users say it's quiet

Are neighbors friendly in Chestertown, MD?

As of early 2026, 61% of users say neighbors are friendly

Is there wildlife in Chestertown, MD?

As of early 2026, 57% of users say there's wildlife

Is Chestertown, MD walkable to restaurants?

As of early 2026, 56% of users say it's walkable to restaurants

Does Chestertown, MD have sidewalks?

As of early 2026, 54% of users say there are sidewalks

Do kids play outside in Chestertown, MD?

As of early 2026, 49% of users say kids play outside

Is Chestertown, MD walkable to grocery stores?

As of early 2026, 46% of users say it's walkable to grocery stores

Are the streets well-lit in Chestertown, MD?

As of early 2026, 44% of users say streets are well-lit

Are there community events in Chestertown, MD?

As of early 2026, 41% of users say there are community events

Do residents of Chestertown, MD plan to stay at least 5 years?

As of early 2026, 38% of users say they plan to stay for at least 5 years

OFF MARKET

159 Flatland Rd
Chestertown, MD 21620

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

$337,700

Trulia Estimate

as of Jun 17, 2026

Est. Refi. Payment $1,969/mo*

Refinance Your Home

$337,700

Trulia Estimate

as of Jun 17, 2026

Est. Refi. Payment $1,969/mo*

Refinance Your Home

3 Beds

2 Baths

1,344 sqft

(on 1.77 acres)

Local Information

-- mins to

Commute Destination

Description

Chestertown rancher with attached garage on 1.7 acres. Two levels, walk-out basement and workshop area, with overhead door. In Town limits.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 159 Flatland Rd

Interior Features
Interior Details Basement
Heating & Cooling Heating: OtherHeating Fuel: Other
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 History for 159 Flatland Rd

Date	Price	Event	Source
01/08/2025	$220,000	Sold	N/A
Recording Date 01/08/2025 Contract Date 01/03/2025 County Transfer Tax $11 Total Transfer Tax $22
01/17/2018	$119,900	ListingRemoved	Agent Provided

09/14/2017	$119,900	PriceChange	Agent Provided
Price Change $10,000 (-8%)
08/25/2016	$129,900	Listed For Sale	Agent Provided

11/16/2011	$295,000	ListingRemoved	Agent Provided

02/26/2011	$295,000	Listed For Sale	Agent Provided

10/29/2003	$120,000	Sold	N/A
Recording Date 10/29/2003 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chestertown

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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Property Tax and Assessment

Year	2025
Tax	$7,952
Assessment	$253,700

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,289/mo

List your home for rent

Homes for rent near 159 Flatland Rd

See what comparable homes in the neighborhood are renting for.

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2 bd
2 ba
160 Flatland Rd #f320a52c6,
Chestertown, MD 21620
2 bd
2 ba
150 Flatland Rd #f320a52c6,
Chestertown, MD 21620
2 bd
2 ba
101 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
2 bd
2 ba
103 Hawkins Dr #f320a52c6,
Chestertown, MD 21620
2 bd
2 ba
200 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
2 bd
2 ba
402 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
2 bd
2 ba
415 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
2 bd
2 ba
200 Clipper Way #f320a52c6,
Chestertown, MD 21620
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Chestertown
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Comparable Sales for 159 Flatland Rd

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
845 High St, Chestertown, MD	0.51	Single-Family Home	$240,000	08/26/25	2	2	1,218
811 S Meadowview Dr, Chestertown, MD	0.72	Single-Family Home	$459,000	06/23/25	3	2	2,064
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	$250,000	07/31/25	4	2	1,325
898 Washington Ave, Chestertown, MD	1.01	Single-Family Home	$237,000	06/30/25	2	2	1,384
25285 Foxchase Dr, Chestertown, MD	1.08	Single-Family Home	$550,000	07/01/25	3	2.5	2,010
8978 Orchard Dr, Chestertown, MD	0.80	Single-Family Home	$680,000	09/30/25	4	2.5	3,820
141 Prospect St, Chestertown, MD	0.86	Single-Family Home	$120,000	02/27/26	4	1.5	1,156

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $293,800
3 bd
1.5 ba
1,152 sqft
306 Roosevelt Dr,
Chestertown, MD 21620
Patterson-Schwartz Real Estate
SOLD
JAN 16, 2026
$255,000
3 bd
2 ba
960 sqft
318 Lincoln Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
SEP 22, 2025
$220,000
3 bd
2.5 ba
1,200 sqft
300 Hilltop Ln,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
SEP 26, 2025
$215,000
3 bd
2.5 ba
1,199 sqft
304 Hilltop Ln,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
Est. $313,900
3 bd
2 ba
1,200 sqft
316 Roosevelt Dr,
Chestertown, MD 21620
Save 6, Incorporated
OFF MARKET
Est. $206,500
3 bd
2.5 ba
1,216 sqft
310 Hilltop Ln,
Chestertown, MD 21620
Cross Street Realtors LLC
OFF MARKET
Est. $317,300
3 bd
2.5 ba
1,404 sqft
102 Lincoln Dr,
Chestertown, MD 21620
RE/MAX First Choice
OFF MARKET
Est. $256,400
4 bd
2.5 ba
1,632 sqft
305 Lincoln Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
JUN 8, 2026
$293,000
3 bd
2 ba
1,152 sqft
301 Lincoln Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
OFF MARKET
Est. $247,500
3 bd
1.5 ba
114 Metcalf Rd,
Chestertown, MD 21620
RE/MAX Executive
OFF MARKET
Est. $262,700
3 bd
1.5 ba
1,140 sqft
118 Metcalf Rd,
Chestertown, MD 21620
RE/MAX Executive
FOR SALE
$340,000
4 bd
2.5 ba
1,972 sqft
214 Silver Heel Rd,
Chestertown, MD 21620
Cross Street Realtors LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 159 Flatland 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
Visitor
3y ago
"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
Visitor
5y ago
"Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
1
Flag
Trulia User
Prev. Resident
5y ago
"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.
Resident
6y ago
"Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
0
Flag
Tracy W.
Resident
6y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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.
11y ago
"Good Community, friendly people, good services. "
0
Flag
Nancy M.
12y ago
"People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
5
Flag
asso
12y ago
"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
12y ago
"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

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
150 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
103 Hawkins Dr #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
402 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Morgnec Rd #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
101 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
501 E Campus Ave #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
160 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Clipper Way #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
415 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
See more homes for rent in
Chestertown
Take a look

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Explore by feature - Air Conditioning

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
$2,200/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware Ave,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,700/mo
2 bd
1 ba
1,100 sqft
27318 Morgnec Rd #B,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620
6 rentals with air conditioning in Chestertown, MD

Explore by feature - Washer/dryer

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
$2,200/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware Ave,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,700/mo
2 bd
1 ba
1,100 sqft
27318 Morgnec Rd #B,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Homes for sale near 159 Flatland Rd

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$340,000
4 bd
2.5 ba
1,972 sqft
214 Silver Heel Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
OPEN SAT, 11-1PM
$399,900
3 bd
2.5 ba
1,944 sqft
103 Trafford Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
0.28 ACRES
$450,000
4 bd
2.5 ba
2,880 sqft
110 Trafford Dr,
Chestertown, MD 21620
RE/MAX Advantage Realty
0.41 ACRES
$314,900
4 bd
2 ba
1,325 sqft
304 Hadaway Dr,
Chestertown, MD 21620
Redfin Corporation
0.28 ACRES
$475,000
4 bd
3 ba
3,504 sqft
311 Devon Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$225,000
3 bd
1 ba
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
$119,900
3 bd
1.5 ba
2,210 sqft
110 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
$499,999
5 bd
3.5 ba
3,932 sqft
218 Camelot Dr,
Chestertown, MD 21620
Coldwell Banker Realty
$429,999
4 bd
2 ba
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
$275,000
2 bd
1.5 ba
920 sqft
611 Cannon St,
Chestertown, MD 21620
Select Land & Homes, LLC
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 159 Flatland Rd

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SOLD
JUN 12, 2026
$249,000
3 bd
1 ba
1,356 sqft
112 Elm St,
Chestertown, MD 21620
Coldwell Banker Waterman Realty
SOLD
JUN 8, 2026
$293,000
3 bd
2 ba
1,152 sqft
301 Lincoln Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
JUN 5, 2026
$175,000
3 bd
1 ba
1,296 sqft
113 Pear Tree Point Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUN 4, 2026
$262,000
2 bd
2 ba
720 sqft
10971 Bottom Rd,
Worton, MD 21678
Keller Williams Select Realtors of Annapolis
SOLD
JUN 4, 2026
$290,000
2 bd
2.5 ba
1,864 sqft
115 Acorn Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
JUN 3, 2026
$355,000
3 ba
3,664 sqft
349 High St,
Chestertown, MD 21620
SOLD
JUN 3, 2026
$264,900
111 Metcalf Rd,
Chestertown, MD 21620
SOLD
MAY 29, 2026
$430,000
3 bd
2 ba
1,588 sqft
201 Birch Run Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
MAY 27, 2026
$300,000
3 bd
1 ba
1,408 sqft
154 Longfellow Dr,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
MAY 26, 2026
$355,000
6 bd
3,664 sqft
349 & 351 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
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159 Flatland Rd, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 1,344 sqft single-family home built in 1955. This property is not currently available for sale. 159 Flatland Rd was last sold on Jan 8, 2025 for $220,000. The current Trulia Estimate for 159 Flatland Rd is $337,700.

159 Flatland Rd
Chestertown, MD 21620

$337,700

$337,700

Local Information