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

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 Round top Rd?

The closest schools to Round top Rd in Chestertown, MD are Church Hill Elementary School (Pre-K, rated 5/10), Queen Anne's County High School (rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).

How big is the lot at Round top Rd?

The lot at Round top Rd in Chestertown, MD is about 6.3 acres .

OFF MARKET

$63,200

Tax assessed value

Studio

Round top Rd, Chestertown, MD 21620

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	Bed	Bath	Sqft
111 Cee Jay Rd, Chestertown, MD	0.98	Single-Family Home	$349,000	10/23/25		2	1,400
111 Cee Jay Rd, Chestertown, MD	0.98	Single-Family Home	$349,000	10/16/25	4	2	1,400
143 Char Nor Manor Blvd, Chestertown, MD	1.12	Single-Family Home	$868,000	10/15/25	3	2.5	2,073
124 Char Nor Manor Blvd, Chestertown, MD	1.04	Single-Family Home	$250,000	11/11/25	2	2	1,024
126 Char Nor Manor Blvd, Chestertown, MD	1.05	Single-Family Home	$349,500	06/05/26	3	2	1,304
148 E Step Rd, Chestertown, MD	1.09	Single-Family Home	$365,000	04/17/26	4	2	1,400
127 Char Nor Manor Blvd, Chestertown, MD	1.06	Single-Family Home	$355,000	10/02/25	2	1	832
129 Char Nor Manor Blvd, Chestertown, MD	1.07	Single-Family Home	$412,000	02/20/26	2	1	810
134 Char Nor Manor Blvd, Chestertown, MD	1.07	Single-Family Home	$260,000	02/18/26	3	1	1,128
236 Merganser Dr, Chestertown, MD	1.21	Single-Family Home	$85,000	10/01/25	1	1	900

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
204 Double Creek Rd, Chestertown, MD 21620	0.64	$545,000	3	2.5	2,927	For Sale
125 Evergreen Farm Ln, Chestertown, MD 21620	0.65	$642,800	1	1	1,296	Off Market
McGinnes Rd, Chestertown, MD 21620	0.95	-	-	-	-	Off Market
109 Snyder Ln, Chestertown, MD 21620	0.97	$145,600	3	2	924	Off Market
906 Double Creek Point, Chestertown, MD 21620	0.98	$325,300	4	2	1,400	Off Market
111 Cee Jay Rd, Chestertown, MD 21620	0.98	-	4	2	1,400	Off Market
127 Wood Duck Ln, Chestertown, MD 21620	0.98	$135,000	3	2	1,666	Recently Sold
118 Char Nor Manor Blvd, Chestertown, MD 21620	1.03	$278,700	3	2	1,114	Off Market
101 Char Nor Manor Blvd, Chestertown, MD 21620	1.03	$385,500	3	1.5	1,156	Off Market
107 Char Nor Manor Blvd, Chestertown, MD 21620	1.03	$424,400	5	3	2,128	Off Market
112 Snyder Ln, Chestertown, MD 21620	1.04	$233,500	2	2	966	Off Market
124 Char Nor Manor Blvd, Chestertown, MD 21620	1.04	$250,000	2	2	1,024	Recently Sold

Local Information

Map ViewExplore the area around Round top Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

6.32 acres

About this House

This single-family home is located at Round top Rd, Chestertown, MD. Round top Rd is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 6.32 acres.

Round top Rd, Chestertown, MD 21620 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,033/month.

Home Details for Round top Rd

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 6.32 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	Unavailable	$63,200

Home facts updated by county records

Additional Cost

Market trends in Chestertown

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

Around this home

Church Hill Elementary School
PK-4
Public
326 Students
Queen Anne's County Public Schools
5/10
GreatSchools Rating
Parent Rating Average
EVERY adult at Church Hill Elementary knows my son and treats him like his/her own. I couldn't have handpicked a better school for my child. CHES, thanks for ALL you do!
Parent Review
8y ago
2 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

Frequently asked questions about Round top Rd

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 Round top Rd?
The closest schools to Round top Rd in Chestertown, MD are Church Hill Elementary School (Pre-K, rated 5/10), Queen Anne's County High School (rated 7/10), Sudlersville Middle School (Elementary, rated 5/10).
How big is the lot at Round top Rd?
The lot at Round top Rd in Chestertown, MD is about 6.3 acres.

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$2,400/mo
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Explore by feature - Air Conditioning

APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,295/mo
1 bd
1 ba
532 Cannon St #5,
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
$1,950/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

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
$1,950/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
$1,750/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620

Apartments for Rent

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Off Market Homes Near Round top Rd

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SOLD
AUG 21, 2026
$289,000
3 bd
1 ba
1,248 sqft
517 Round Top Rd,
Chestertown, MD 21620
Keller Williams Flagship
SOLD
AUG 18, 2026
$380,000
5 bd
3.5 ba
2,534 sqft
107 Flying Cloud Dr,
Chestertown, MD 21620
CENTURY 21 New Millennium
SOLD
AUG 17, 2026
$339,900
3 bd
2 ba
1,250 sqft
102 Pine St,
Crumpton, MD 21628
Clark & Co Realty, LLC
SOLD
AUG 16, 2026
$525,000
3 bd
3 ba
2,824 sqft
Preston Ln,
Chestertown, MD 21620
Shoreline Realty
SOLD
AUG 14, 2026
$318,000
3 bd
2 ba
1,397 sqft
109 Cedar St,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
AUG 14, 2026
$1,200,000
4 bd
3 ba
2,292 sqft
202 Royston Shores Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
AUG 14, 2026
$42,000
228 Merganser Dr,
Chestertown, MD 21620
Benson & Mangold, LLC
SOLD
AUG 14, 2026
$324,000
3 bd
2.5 ba
1,896 sqft
102 Flying Cloud Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
SOLD
AUG 13, 2026
$75,000
East St,
Chestertown, MD 21620
Select Land & Homes, LLC
SOLD
AUG 10, 2026
$247,500
3 bd
1 ba
1,967 sqft
1904 Pondtown Rd,
Chestertown, MD 21620
Keller Williams Flagship
See more homes for sale in
Chestertown
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Homes for sale near Round top Rd

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0.87 ACRES
$545,000
3 bd
2.5 ba
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.34 ACRES
$299,900
3 bd
1 ba
1,056 sqft
124 Wilton Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.67 ACRES
$320,000
3 bd
1.5 ba
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
COMING SOON 9/2
0.34 ACRES
$315,000
3 bd
2 ba
1,288 sqft
109 Parma Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
NEW
COMING SOON 9/2
0.34 ACRES
$345,000
3 bd
1.5 ba
1,398 sqft
217 Edmore Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
COMING SOON 9/1
0.55 ACRES
$225,000
4 bd
1.5 ba
1,800 sqft
533 Round Top Rd,
Chestertown, MD 21620
EXP Realty, LLC
1 ACRE
$295,000
3 bd
2 ba
1,132 sqft
240 Round Top Rd,
Chestertown, MD 21620
Clark & Co Realty, LLC
1.03 ACRES
$395,000
2 bd
1.5 ba
1,440 sqft
224 Ewingtown Rd,
Church Hill, MD 21623
Doug Ashley Realtors, LLC
0.46 ACRES
$337,500
3 bd
2 ba
1,250 sqft
209 3rd St,
Crumpton, MD 21628
EXP Realty, LLC
0.3 ACRES
$200,000
3 bd
1.5 ba
2,206 sqft
107 2nd St,
Crumpton, MD 21628
Marathon Real Estate
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