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 buyer'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 7/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).

OFF MARKET

$37,500

Last sold price

1,624 sqft (on 4.66 acres)

415 Pine Tree Rd, Chestertown, MD 21620

Currently Off Market - Sold Feb 23, 2015 for $37,500

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
206 Burchard Sawmill Rd, Chestertown, MD	1.22	Lot/Land	$9,000	07/08/26	-	-
116 2nd St, Crumpton, MD	2.05	Lot/Land	$75,000	05/06/26	-	-
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	-	-
400 Chester River Heights Rd, Millington, MD	4.04	Lot/Land	$325,000	08/05/26	-	1,170
228 Merganser Dr, Chestertown, MD	3.37	Lot/Land	$42,000	08/14/26	-	-
E Step Rd, Chestertown, MD	3.54	Lot/Land	$365,000	04/21/26	-	1
10669 Chesterville Forest Rd, Millington, MD	4.41	Lot/Land	$130,000	06/30/26	-	215,361
144 Char Nor Manor Blvd, Chestertown, MD	3.61	Lot/Land	$50,000	04/29/26	-	-

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
417 Pine Tree Rd, Chestertown, MD 21620	0.06	$102,400	Studio	1	760	Off Market
419 Pine Tree Rd, Chestertown, MD 21620	0.06	-	-	-	-	Off Market
421 Pine Tree Rd, Chestertown, MD 21620	0.08	$103,400	Studio	1	640	Off Market
411A Pine Tree Rd, Chestertown, MD 21620	0.09	$676,500	3	3	1,844	Off Market
411B Pine Tree Rd, Chestertown, MD 21620	0.09	$356,200	Studio	2	1,095	Off Market
411 Pine Tree Rd, Chestertown, MD 21620	0.09	$672,300	3	3	-	Off Market
413A Pine Tree Rd, Chestertown, MD 21620	0.09	$308,900	Studio	2	1,232	Off Market
413 Pine Tree Rd, Chestertown, MD 21620	0.09	$306,000	3	2	1,232	Off Market
425 Pine Tree Rd, Chestertown, MD 21620	0.09	$177,700	Studio	1	1,300	Off Market
426 Pine Tree Rd, Chestertown, MD 21620	0.10	$368,300	Studio	3	1,680	Off Market
422 Pine Tree Rd, Chestertown, MD 21620	0.10	$184,800	Studio	3	2,016	Off Market
1814 Pondtown Rd, Chestertown, MD 21620	0.13	$90,200	3	1	973	Off Market
427 Pine Tree Rd, Chestertown, MD 21620	0.13	-	-	-	-	Off Market
1810 Pondtown Rd, Chestertown, MD 21620	0.13	$179,700	Studio	1	960	Off Market
105 Pearl Creek Ln, Chestertown, MD 21620	0.14	$459,000	3	2.5	1,961	Recently Sold
111 Pearl Creek Ln, Chestertown, MD 21620	0.14	$399,300	-	-	1,709	Off Market
435 Pine Tree Rd, Chestertown, MD 21620	0.17	$341,400	Studio	2	1,344	Off Market
104 Freeman Ln, Chestertown, MD 21620	0.17	$255,300	Studio	2	1,144	Off Market
1822 Pondtown Rd, Chestertown, MD 21620	0.17	$327,200	Studio	2	1,568	Off Market
121 Pearl Creek Ln, Chestertown, MD 21620	0.17	$382,500	3	2.5	1,188	Off Market

Local Information

Map ViewExplore the area around 415 Pine Tree Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Lot/Land

Built in 2020

4.66 acre lot

1,624 sqft

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. This property is not currently displayed as for sale or rent on Trulia.

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

Additional Cost

Market trends in Chestertown

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Sourced by Trulia Market Trends

Around this home

Sudlersville Elementary School
PK-4
Public
297 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
16y 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
4y 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
7y 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
13y 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

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 buyer'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 7/10), Sudlersville Elementary School (Pre-K, rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).

Apartments for Rent

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Off Market Homes Near 415 Pine Tree Rd

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SOLD
OCT 30, 2026
$555,000
1 bd
2 ba
760 sqft
114 Front St,
Crumpton, MD 21628
Coldwell Banker Chesapeake Real Estate Company
SOLD
OCT 22, 2026
$650,000
3 bd
2.5 ba
2,160 sqft
209 Shoals Rd,
Crumpton, MD 21628
Doug Ashley Realtors, LLC
SOLD
OCT 16, 2026
$337,500
3 bd
2 ba
1,250 sqft
209 3rd St,
Crumpton, MD 21628
EXP Realty, LLC
SOLD
OCT 16, 2026
$525,000
3 bd
2.5 ba
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
OCT 8, 2026
$165,000
3 bd
1 ba
1,056 sqft
1801 Sudlersville Rd,
Sudlersville, MD 21668
SOLD
OCT 2, 2026
$470,000
3 bd
2.5 ba
1,574 sqft
405 Chester River Heights Rd,
Millington, MD 21651
Village Real Estate Company LLC
SOLD
OCT 2, 2026
$399,000
3 bd
2 ba
1,512 sqft
100 Clark Ct,
Millington, MD 21651
Berkshire Hathaway Homeservice Homesale Realty
SOLD
SEP 28, 2026
$220,000
3 bd
2 ba
22,872 sqft
104 Wood Duck Ln,
Chestertown, MD 21620
SOLD
SEP 16, 2026
$360,000
3 bd
2 ba
1,120 sqft
240 Merganser Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
SEP 10, 2026
$100,000
1 ba
1,101 sqft
641 Pondtown Rd,
Sudlersville, MD 21668
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