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

What is the price history for 415 Pine Tree Rd?

415 Pine Tree Rd in Chestertown, MD last sold for $37,500 in February 2015.

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 .

What are the closest schools to 415 Pine Tree Rd?

The closest schools to 415 Pine Tree Rd in Chestertown, MD are Queen Anne's County High School (rated 4/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).

OFF MARKET

415 Pine Tree Rd
Chestertown, MD 21620

1,624 sqft (on 4.66 acres)

1,624 sqft

(on 4.66 acres)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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	Bath	Sqft
404 Spring Rd, Chestertown, MD	0.73	Lot/Land	$1,201	08/29/25	-	-
206 Burchard Sawmill Rd, Chestertown, MD	1.22	Lot/Land	$9,000	07/08/26	-	-
Second, Crumpton, MD	1.56	Lot/Land	$107,000	09/08/25	-	-
2nd St, Crumpton, MD	1.94	Lot/Land	$107,000	09/08/25	-	-
220 Shoals Rd, Crumpton, MD	2.02	Lot/Land	$119,000	10/24/25	-	-
116 2nd St, Crumpton, MD	2.05	Lot/Land	$75,000	05/06/26	-	-
McGinnes Rd, Chestertown, MD	2.40	Lot/Land	$75,000	09/26/25	-	-
3607 McGinnes Rd, Millington, MD	2.53	Lot/Land	$78,000	04/10/26	-	-
Hoffecker Rd, Chestertown, MD	2.60	Lot/Land	$190,000	03/04/26	-	-
109 2nd St, Chestertown, MD	2.94	Lot/Land	$75,000	12/08/25	-	-

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
105 Pearl Creek Ln, Chestertown, MD 21620	0.14	$459,000	3	2.5	1,961	Recently Sold
1814 Pondtown Rd, Chestertown, MD 21620	0.13	$90,600	3	1	973	Off Market
340 Pine Tree Rd, Chestertown, MD 21620	0.26	$241,200	Studio	-	1,080	Off Market
136 Pearl Creek Ln, Chestertown, MD 21620	0.30	-	3	2.5	1,460	Off Market
1904 Pondtown Rd, Chestertown, MD 21620	0.29	$247,500	3	1	1,967	Recently Sold
1906 Pondtown Rd, Chestertown, MD 21620	0.30	$110,000	-	-	-	For Sale
305 Pine Tree Rd, Chestertown, MD 21620	0.47	$273,600	2	1	826	Off Market
2032 Pondtown Rd, Chestertown, MD 21620	0.46	$365,000	3	2	1,120	Recently Sold
200 Ashley Ln, Chestertown, MD 21620	0.52	$478,300	3	1.5	1,656	Off Market
206 Springbrook Ln, Millington, MD 21651	0.61	$449,600	3	2	1,680	Off Market
108 Springbrook Ln, Millington, MD 21651	0.67	$475,900	3	2	1,677	Recently Sold
Par 113 Spring Rd, Millington, MD 21651	0.70	-	-	-	-	Off Market

Local Information

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Home Highlights

Property Type

Lot/Land

Year Built

2020

Lot Size

4.66 acres

Living Area

1,624 sqft

Parking

Garage

About this House

Perc Approved, Private Country Setting on 4.66 Acres. Design the home of your dreams and place it exactly where you want it. Great Partially wooded lot with nature abounding at every turn. Land is also great for hunting.

415 Pine Tree Rd, Chestertown, MD 21620 is a 1,624 sqft lot/land built in 2020. It last sold for $37,500 on Feb 23, 2015. It is currently off market. The Trulia Estimate rent is $1,872/month.

Home Details for 415 Pine Tree Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1

Exterior Features
Exterior Home Features Roof: OtherExterior: Other
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2020
Property Type / Style Property Type: Lot LandArchitecture: Other

Community
Units in Building: 1

Lot Information
Lot Area: 4.66 acres

Price and Tax history

Date	Event	Price
Feb 23, 2015 Source: N/A	Sold	$37,500
Oct 8, 2014 Source: Agent Provided	ListingRemoved	$49,900
May 26, 2014 Source: Agent Provided	PriceChange	$49,900 Price decreased by 15%
Apr 10, 2014 Source: Agent Provided	Listed For Sale	$59,000
Mar 10, 2014 Source: Agent Provided	ListingRemoved	$63,000
Nov 8, 2013 Source: Agent Provided	PriceChange	$63,000 Price decreased by 4%
Oct 4, 2012 Source: Agent Provided	PriceChange	$65,500 Price decreased by 1%
Jul 6, 2012 Source: Agent Provided	PriceChange	$66,000 Price decreased by 4%
May 29, 2012 Source: Agent Provided	Listed For Sale	$69,000
Apr 28, 2010 Source: N/A	Sold	$65,000

Year	Property tax	Tax assessment
2025	$3,371	$357,900

Market trends in Chestertown

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

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Additional Cost

Around this home

Sudlersville Elementary School
PK-4
Public
315 Students
Queen Anne's County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
Unfortunately, my family had to move out of this school district, and it was the worst mistake I ever made! I love this school. They are outstanding- teachers, principal, staff, even the cafeteria and janitorial staff were excellent. My children had an awesome experience at this school!
Parent Review
15y ago
3 Reviews

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
8y 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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Explore by feature - Pet Friendly

6 pet-friendly rentals in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$1,295/mo
1 bd
1 ba
532 Cannon St #5,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,400/mo
2 bd
2.5 ba
1,536 sqft
103 S College Ave,
Chestertown, MD 21620
PET FRIENDLY
$1,850/mo
3 bd
2.5 ba
1,520 sqft
206 N Mill St,
Chestertown, MD 21620
PET FRIENDLY
$1,820/mo
2 bd
2 ba
900 sqft
104 Maple Ave #4,
Chestertown, MD 21620
PET FRIENDLY
$1,500/mo
3 bd
1 ba
1,272 sqft
2201 Pondtown Rd,
Chestertown, MD 21620

Explore by feature - Air Conditioning

6 rentals with air conditioning in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$1,295/mo
1 bd
1 ba
532 Cannon St #5,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,400/mo
2 bd
2.5 ba
1,536 sqft
103 S College Ave,
Chestertown, MD 21620
PET FRIENDLY
$1,850/mo
3 bd
2.5 ba
1,520 sqft
206 N Mill St,
Chestertown, MD 21620
PET FRIENDLY
$1,820/mo
2 bd
2 ba
900 sqft
104 Maple Ave #4,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620

Explore by feature - Washer/dryer

APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,400/mo
2 bd
2.5 ba
1,536 sqft
103 S College Ave,
Chestertown, MD 21620
PET FRIENDLY
$1,850/mo
3 bd
2.5 ba
1,520 sqft
206 N Mill St,
Chestertown, MD 21620
PET FRIENDLY
$1,820/mo
2 bd
2 ba
900 sqft
104 Maple Ave #4,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620

Homes for sale near 415 Pine Tree Rd

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1.93 ACRES
$110,000
1906 Pondtown Rd,
Chestertown, MD 21620
Keller Williams Flagship
0.99 ACRES
$19,500
404 Spring Rd,
Chestertown, MD 21620
The Parker Group
1.8 ACRES
$135,000
109 2nd St,
Chestertown, MD 21620
Cross Street Realtors LLC
1.49 ACRES
$249,000
Chester River Heights Rd,
Millington, MD 21651
Select Land & Homes, LLC
0.5 ACRES
$60,000
233 Merganser Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.95 ACRES
$85,000
104 Pfalzgroff Rd,
Millington, MD 21651
RE/MAX Executive
15 ACRES
$195,000
Chestervl Millington Rd,
Millington, MD 21651
Keller Williams Realty Wilmington
OFF MARKET
Old Morgnec Rd,
Chestertown, MD 21620
1.37 ACRES
$59,000
Old Morgnec Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
5 ACRES
$80,000
Parcel 38 Goldsboro Rd,
Barclay, MD 21607
Benson & Mangold, LLC
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 415 Pine Tree Rd

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SOLD
AUG 10, 2026
$247,500
3 bd
1 ba
1,967 sqft
1904 Pondtown Rd,
Chestertown, MD 21620
Keller Williams Flagship
SOLD
AUG 7, 2026
$180,000
3 bd
1 ba
1,440 sqft
1826 Sudlersville Rd,
Sudlersville, MD 21668
212 Degrees Realty, LLC
SOLD
JUL 31, 2026
$108,000
222 Lakeside Dr,
Millington, MD 21651
SOLD
JUL 21, 2026
$599,900
12 bd
4 ba
5,239 sqft
106 CHARLES STREET,
Sudlersville, MD 21668
SOLD
JUL 15, 2026
$275,000
Crumpton Rd,
Crumpton, MD 21628
SOLD
JUL 8, 2026
$9,000
206 Burchard Sawmill Rd,
Chestertown, MD 21620
XRealty.NET LLC
SOLD
JUL 6, 2026
$760,000
2 ba
3,400 sqft
1614 Dudley Corners Rd,
Millington, MD 21651
SOLD
JUN 30, 2026
$34,000
Shadingreach Rd,
Galena, MD 21635
SOLD
JUN 30, 2026
$34,000
Chesterville Forest Rd #60,
Millington, MD 21651
Chesapeake Real Estate Associates, LLC
SOLD
JUN 29, 2026
$460,000
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
See more homes for sale in
Chestertown
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Frequently asked questions about 415 Pine Tree Rd

What is the price history for 415 Pine Tree Rd?
415 Pine Tree Rd in Chestertown, MD last sold for $37,500 in February 2015.
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.
What are the closest schools to 415 Pine Tree Rd?
The closest schools to 415 Pine Tree Rd in Chestertown, MD are Queen Anne's County High School (rated 4/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).

415 Pine Tree Rd
Chestertown, MD 21620