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

Pine Tree Rd
Chestertown, MD 21620

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Local Information

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Description

Pine Tree Rd is in Chestertown, MD and in ZIP code 21620.

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.

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Comparable Sales for Pine Tree Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
176 Flatland Rd, Chestertown, MD	0.37	Single-Family Home	$800,000	02/17/26		-	3,476
8978 Orchard Dr, Chestertown, MD	0.53	Single-Family Home	$680,000	09/30/25	4	2.5	3,820
318 Lincoln Dr, Chestertown, MD	0.53	Single-Family Home	$255,000	01/16/26	3	2	960
845 High St, Chestertown, MD	0.53	Single-Family Home	$240,000	08/26/25	2	2	1,218
8951 Orchard Dr, Chestertown, MD	0.64	Single-Family Home	$700,000	12/04/25	4	3.5	3,735
25285 Foxchase Dr, Chestertown, MD	0.73	Single-Family Home	$550,000	07/01/25	3	2.5	2,010
103 Adela Way, Chestertown, MD	0.78	Single-Family Home	$585,000	11/13/25	4	3.5	5,576
100 Adela Way, Chestertown, MD	0.81	Single-Family Home	$490,000	05/08/26	4	3.5	3,799
619 Cannon St, Chestertown, MD	0.85	Single-Family Home	$190,500	07/22/25	1	1	882
101 S Lynchburg St, Chestertown, MD	0.86	Single-Family Home	$19,000	07/14/25		-	240

Assigned Schools

These are the assigned schools for Pine Tree 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

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
4y 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.
11y 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
501 E Campus Ave #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
200 Clipper Way #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
415 Morgnec 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
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 Morgnec Rd #776f18ccb,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
NEW - 1 DAY AGO
APPLY INSTANTLY
$1,100/mo
Total price
1 ba
866 Washington Ave #B,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
PET FRIENDLY
$1,520/mo
2 bd
1 ba
104 Maple Ave #3,
Chestertown, MD 21620
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Chestertown
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Homes for sale near Pine Tree Rd

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$350,000
4 bd
2.5 ba
1,972 sqft
214 Silver Heel Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
COMING SOON 5/20
2.16 ACRES
$425,000
3 bd
2 ba
1,440 sqft
8629 Airy Hill Rd,
Chestertown, MD 21620
Keller Williams Realty
$419,900
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
OPEN SAT, 10-12PM
$510,000
5 bd
3.5 ba
3,932 sqft
218 Camelot Dr,
Chestertown, MD 21620
Coldwell Banker Realty
$550,000
5 bd
3.5 ba
3,816 sqft
103 Sutton Way,
Chestertown, MD 21620
TTR Sotheby's International Realty
$179,000
2 bd
1.5 ba
1,082 sqft
144 Prospect St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$225,000
3 bd
1 ba
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
$275,000
2 bd
1.5 ba
920 sqft
611 Cannon St,
Chestertown, MD 21620
Select Land & Homes, LLC
$419,900
3 bd
2.5 ba
1,216 sqft
109 S College Ave,
Chestertown, MD 21620
Taylor Properties
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Additional Cost

Homes for rent near Pine Tree Rd

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NEW - 1 DAY AGO
APPLY INSTANTLY
$2,150/mo
3 bd
2.5 ba
1,365 sqft
110 Island Lark Way,
Chestertown, MD 21620
APPLY INSTANTLY
$2,095/mo
3 bd
2.5 ba
1,222 sqft
210 Hilltop Ln,
Chestertown, MD 21620
NEW - 1 DAY AGO
$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
PET FRIENDLY
$1,520/mo
2 bd
1 ba
800 sqft
104 Maple Ave #3,
Chestertown, MD 21620
See more homes for rent in
Chestertown
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Off Market Homes Near Pine Tree Rd

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SOLD
MAY 14, 2026
$278,500
3 bd
1 ba
107 Longfellow Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 8, 2026
$490,000
4 bd
3.5 ba
3,799 sqft
100 Adela Way,
Chestertown, MD 21620
Berkshire Hathaway HomeServices PenFed Realty
SOLD
MAY 1, 2026
$370,000
3 bd
1.5 ba
1,404 sqft
217 Philosophers Ter,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
APR 30, 2026
$545,000
4 bd
2.5 ba
2,008 sqft
206 S Water St,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
APR 21, 2026
$339,900
3 bd
2.5 ba
1,724 sqft
103 Flying Cloud Dr,
Chestertown, MD 21620
American Premier Realty, LLC
SOLD
APR 17, 2026
$495,000
4 bd
2.5 ba
2,220 sqft
515 N Kent St,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
APR 17, 2026
$480,000
3 bd
2 ba
1,734 sqft
104 Garland Ave,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
APR 17, 2026
$495,000
4 bd
3 ba
3,984 sqft
201 Greenwood Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
APR 14, 2026
$220,000
4 bd
1 ba
1,248 sqft
513 Round Top Rd,
Chestertown, MD 21620
Cummings & Co. Realtors
SOLD
APR 13, 2026
$749,500
3 bd
2.5 ba
3,136 sqft
6 Byford Ct,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
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