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

103 Pine St
Chestertown, MD 21620

2 Beds
2 Baths
1,132 sqft (on 0.31 acres)

$290,300

Trulia Estimate

as of Jul 5, 2026

Est. Refi. Payment $1,705/mo*

Refinance Your Home

$290,300

Trulia Estimate

as of Jul 5, 2026

Est. Refi. Payment $1,705/mo*

Refinance Your Home

2 Beds

2 Baths

1,132 sqft

(on 0.31 acres)

Local Information

Map ViewExplore the area around 103 Pine St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Great blend of the updated & the original. Cute as a button ranch home features updated kitchen, huge basement family room w/ pellet stove, brand new roof, replacement windows. Gorgeous refinished oak hardwoods, built in corner cabinet, fireplace mantel, bathroom & laundry addition on rear of home. Close to college, hospital, and all that Chestertown has to offer. 1 car detached garage "AS IS"

103 Pine St, Chestertown, MD 21620 is a 2 bedroom, 2 bathroom, 1,132 sqft single-family home built in 1951. It last sold for $164,900 on Dec 31, 2016. It is currently off market. The Trulia Estimate is $290,300, with a rent estimate of $1,800/month.

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 103 Pine St

Interior Features
Interior Details Basement
Heating & Cooling Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2
Appliances & Utilities DishwasherMicrowaveRefrigerator
Fireplace & Spa Fireplace

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

Property Information
Year Built Year Built: 1951
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.31 acres

Price History for 103 Pine St

Date	Price	Event	Source
12/31/2016	$164,900	Sold	N/A
Recording Date 12/31/2016 County Transfer Tax N/A Total Transfer Tax N/A
11/03/2016	$164,900	Pending	Agent Provided

10/19/2016	$164,900	Listed For Sale	Agent Provided

08/07/2009	$107,000	Sold	N/A
Recording Date 08/07/2009 Contract Date 08/04/2009 County Transfer Tax N/A Total Transfer Tax N/A
04/03/2009	$149,000	ListingRemoved	Agent Provided

01/26/2009	$149,000	Listed For Sale	Agent Provided

04/30/1998	$75,000	Sold	N/A
Recording Date 04/30/1998 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	$5,187
Assessment	$165,500

Home facts updated by county records

Comparable Sales for 103 Pine St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
304 Hadaway Dr, Chestertown, MD	0.09	Single-Family Home	$250,000	07/31/25	4	2	1,325
112 Elm St, Chestertown, MD	0.07	Single-Family Home	$249,000	06/12/26	3	1	1,356
205 Pine St, Chestertown, MD	0.18	Single-Family Home	$296,337	09/30/25	3	1.5	2,212
108 Pine St, Chestertown, MD	0.05	Single-Family Home	$85,000	06/30/26	3	1	910
204 Rolling Rd, Chestertown, MD	0.30	Single-Family Home	$340,000	03/19/26	3	2	2,296
411 Greenwood Ave, Chestertown, MD	0.23	Single-Family Home	$415,000	01/07/26	3	2.5	1,676
111 Pine St, Chestertown, MD	0.06	Single-Family Home	$347,000	05/05/26	5	1	1,645
126 Metcalf Rd, Chestertown, MD	0.31	Single-Family Home	$230,000	11/20/25	3	2	1,140
224 Valley Rd, Chestertown, MD	0.28	Single-Family Home	$455,000	10/21/25	3	2	1,886
303 E Campus Ave, Chestertown, MD	0.48	Single-Family Home	$364,000	01/16/26	3	2	1,532

Nearby homes

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

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OFF MARKET
Est. $304,600
3 bd
1 ba
1,376 sqft
106 Pine St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUN 30, 2026
$85,000
3 bd
1 ba
910 sqft
108 Pine St,
Chestertown, MD 21620
Real Broker, LLC
SOLD
JUN 12, 2026
$249,000
3 bd
1 ba
1,356 sqft
112 Elm St,
Chestertown, MD 21620
Coldwell Banker Waterman Realty
OFF MARKET
Est. $271,500
3 bd
1 ba
1,275 sqft
111 Elm St,
Chestertown, MD 21620
Keller Williams Select Realtors of Annapolis
OFF MARKET
Est. $455,200
3 bd
2.5 ba
2,008 sqft
118 Elm St,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
APR 17, 2026
$495,000
4 bd
3 ba
3,984 sqft
201 Greenwood Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
SEP 30, 2025
$296,337
3 bd
1.5 ba
2,212 sqft
205 Pine St,
Chestertown, MD 21620
Davis Real Estate, Inc.
SOLD
JAN 7, 2026
$415,000
3 bd
2.5 ba
1,676 sqft
411 Greenwood Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $294,500
3 bd
1 ba
1,252 sqft
202 Glen St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUN 17, 2026
$325,000
3 bd
1 ba
1,427 sqft
202 Valley Rd,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
JAN 12, 2026
$590,000
4 bd
2 ba
2,869 sqft
206 Valley Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
JAN 30, 2026
$325,000
3 bd
2.5 ba
2,577 sqft
303 Cedar St,
Chestertown, MD 21620
Select Land & Homes, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 103 Pine St.

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
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
402 Morgnec 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
150 Flatland Rd #f320a52c6,
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
501 E Campus Ave #776f18ccb,
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
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Explore by feature - Air Conditioning

8 rentals with air conditioning in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$2,075/mo
3 bd
1.5 ba
1,280 sqft
108 Metcalf Rd,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$2,000/mo
3 bd
1 ba
1,122 sqft
351 Calvert St,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$2,075/mo
3 bd
1.5 ba
1,280 sqft
108 Metcalf Rd,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
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 103 Pine St

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0.34 ACRES
$380,000
4 bd
2 ba
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$419,999
4 bd
2 ba
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.34 ACRES
$325,000
3 bd
1 ba
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$329,900
3 bd
2.5 ba
1,896 sqft
102 Flying Cloud Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
$100,000
2 bd
1 ba
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
$89,900
3 bd
1.5 ba
2,210 sqft
110 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
$399,900
2 bd
3 ba
1,518 sqft
522 High St,
Chestertown, MD 21620
Benson & Mangold, LLC
$385,000
5 bd
3.5 ba
2,534 sqft
107 Flying Cloud Dr,
Chestertown, MD 21620
CENTURY 21 New Millennium
$515,000
2 bd
2.5 ba
1,476 sqft
101 S Mill St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 103 Pine St

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SOLD
JUN 26, 2026
$190,000
3 bd
1.5 ba
1,136 sqft
423 Calvert St,
Chestertown, MD 21620
Compass
SOLD
JUN 26, 2026
$410,000
3 bd
2.5 ba
1,216 sqft
109 S College Ave,
Chestertown, MD 21620
Taylor Properties
SOLD
JUN 25, 2026
$395,000
3 bd
2 ba
1,440 sqft
8629 Airy Hill Rd,
Chestertown, MD 21620
Keller Williams Realty
SOLD
JUN 24, 2026
$270,000
134 Prospect St,
Chestertown, MD 21620
SOLD
JUN 17, 2026
$325,000
3 bd
1 ba
1,427 sqft
202 Valley Rd,
Chestertown, MD 21620
TTR Sotheby's International Realty
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
$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
See more homes for sale in
Chestertown
Take a look

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103 Pine St
Chestertown, MD 21620

$290,300

$290,300

Local Information