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

SHELDRAKE Dr
Chestertown, MD 21620

(on 0.34 acres)

Home Value

Learn more about this home's value by checking out 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	Bed	Bath	Sqft
10720 Mendenhall Loop Rd, Juneau, AK	6.22	Single-Family Home	-	08/27/25	4	2.5	2,532

Home facts updated by county records

Local Information

Map ViewExplore the area around SHELDRAKE Dr.
Schools1 Preschool School1 Elementary School2 Middle Schools2 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Lot Size

0.34 acres

About this House

SHELDRAKE Dr is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 0.34 acres.

SHELDRAKE Dr, Chestertown, MD 21620 is a unknown. It last sold for $6,000 on Sep 14, 2005. It is currently off market. The Trulia Estimate rent is $1,644/month.

Home Details for SHELDRAKE Dr

Property Information
Property Type / Style Property Type: Unknown

Interior Features
Fireplace & Spa Fireplace

Lot Information
Lot Area: 0.34 acres

Price and Tax history

Date	Event	Price
Sep 14, 2005 Source: N/A	Sold	$6,000

Year	Property tax	Tax assessment
2025	$68	$3,000

Additional Cost

Market trends in Chestertown

Last updated July 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

5MoM

Around this home

Homebridge
PK-12
Public
224 Students
Juneau Borough School District
4/10
GreatSchools Rating
Parent Rating Average
No reviews available for this school.

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
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Trulia User
Visitor
5y ago
"Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
1
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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
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Kesha C.
Resident
6y ago
"Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
0
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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
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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
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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
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Guillermo A.
11y ago
"Good Community, friendly people, good services. "
0
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Nancy M.
12y ago
"People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
5
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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
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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
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SHELDRAKE Dr
Chestertown, MD 21620