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

Gateway Dr
Chestertown, MD 21620

(on 1.09 acres)

Local Information

Map ViewExplore the area around Gateway Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Lot/Land

Lot Size

1.09 acres

About this House

This lot/land is located at Gateway Dr, Chestertown, MD. Gateway Dr is in Chestertown, MD and in ZIP code 21620. This property has a lot size of 1.09 acres.

Gateway Dr, Chestertown, MD 21620 is a lot/land. It last sold for $100,000 on May 20, 2024. It is currently off market. The Trulia Estimate rent is $1,219/month.

Home Details for Gateway Dr

Property Information
Property Type / Style Property Type: Lot Land

Interior Features
Fireplace & Spa Fireplace

Lot Information
Lot Area: 1.09 acres

Price History for Gateway Dr

Date	Price	Event	Source
05/20/2024	$100,000	Sold	N/A
Recording Date 05/20/2024 Contract Date 05/09/2024 County Transfer Tax $5 Total Transfer Tax $10
09/22/2020	$69,500	Sold	N/A
Recording Date 09/22/2020 Contract Date 09/15/2020 County Transfer Tax $3 Total Transfer Tax $7
07/07/2020	$69,500	Listed For Sale	Agent Provided

01/10/2003	$21,000	Sold	N/A
Recording Date 01/10/2003 County Transfer Tax N/A Total Transfer Tax N/A
06/26/2001	$8,500	Sold	N/A
Recording Date 06/26/2001 County Transfer Tax N/A Total Transfer Tax N/A
06/24/1994	$10,000	Sold	N/A
Recording Date 06/24/1994 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chestertown

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

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Available listings

5MoM

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Property Tax and Assessment

Year	2025
Tax	$1,272
Assessment	$56,100

Home facts updated by county records

Comparable Sales for Gateway Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bath	Sqft
134 Prospect St, Chestertown, MD	1.51	Lot/Land	$270,000	06/24/26	-	-
Millbrook Dr, Chestertown, MD	1.64	Lot/Land	$9,500	08/19/25	-	-
206 Cannon St, Chestertown, MD	2.07	Lot/Land	$800,000	01/15/26	-	-
209 River Rd, Chestertown, MD	2.90	Lot/Land	$124,000	08/25/25	-	-
136 Truslow Farm Ln, Chestertown, MD	2.51	Lot/Land	$560,000	10/31/25	-	-
Bottom Rd, Worton, MD	3.58	Lot/Land	$58,000	03/24/26	-	-
Station Rd, Worton, MD	4.01	Lot/Land	$60,000	10/31/25	-	-
11200 Boyer Ln, Worton, MD	3.95	Lot/Land	$75,000	07/07/26	-	-
144 Char Nor Manor Blvd, Chestertown, MD	4.64	Lot/Land	$50,000	04/29/26	-	-
23698 L Rd, Chestertown, MD	4.52	Lot/Land	$15,000	05/15/26	-	-

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Gateway Dr,
Chestertown, MD 21620
Cottage Street Realty LLC
OFF MARKET
Est. $393,800
3 bd
2.5 ba
1,800 sqft
1006 Twin Ct,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
FOR SALE
3D VIEW
0.69 ACRES
$275,000
3 bd
1 ba
1,248 sqft
956 Washington Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
FOR SALE
NEW - 2 DAYS AGO
0.74 ACRES
$375,000
4 bd
2 ba
1,476 sqft
1010 Twin Ct,
Chestertown, MD 21620
Kevin Dey Realty
SOLD
JUN 26, 2026
$525,000
3 bd
2 ba
1,817 sqft
1014 Twin Ct,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
DEC 1, 2025
$375,000
3 bd
2.5 ba
1,842 sqft
907 N Meadowview Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $241,200
2 bd
2 ba
1,384 sqft
898 Washington Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
FOR SALE
0.34 ACRES
$325,000
3 bd
1 ba
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $534,300
4 bd
2.5 ba
3,016 sqft
201 Pondview Ct,
Chestertown, MD 21620
Cross Street Realtors LLC
OFF MARKET
Est. $548,900
5 bd
3.5 ba
2,878 sqft
207 Pondview Ct,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
OFF MARKET
Est. $497,000
4 bd
3.5 ba
3,000 sqft
100 Foxview Ct,
Chestertown, MD 21620
Rock Hall Properties Real Estate
OFF MARKET
Est. $425,300
3 bd
2 ba
1,509 sqft
813 S Meadowview Dr,
Chestertown, MD 21620
TTR Sotheby's International Realty

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Additional Cost

Assigned Schools

These are the assigned schools for Gateway Dr.

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
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.
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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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
402 Morgnec 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
103 Hawkins Dr #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
200 Clipper Way #776f18ccb,
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
501 E Campus Ave #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Morgnec Rd #776f18ccb,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
PET FRIENDLY
$1,820/mo
2 bd
2 ba
104 Maple Ave #4,
Chestertown, MD 21620
PET FRIENDLY
$1,920/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
See more homes for rent in
Chestertown
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Homes for sale near Gateway Dr

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0.85 ACRES
$250,000
Scheeler Rd #2,
Chestertown, MD 21620
Select Land & Homes, LLC
0.87 ACRES
$225,000
Haacke Dr #3,
Chestertown, MD 21620
Select Land & Homes, LLC
0.61 ACRES
$60,000
305 Roosevelt Dr,
Chestertown, MD 21620
Taylor Properties
0.52 ACRES
$22,900
E Step,
Chestertown, MD 21620
$300,000
201 N Lynchburg St #&-7,
Chestertown, MD 21620
RE/MAX Associates-Hockessin
$750,000
201 N Lynchburg St,
Chestertown, MD 21620
RE/MAX Associates-Hockessin
$635,000
108 Little Harbor Way,
Chestertown, MD 21620
Gunther-McClary Real Estate
5.81 ACRES
$200,000
Round Top Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
1.09 ACRES
$49,000
Lambs Meadow Rd,
Worton, MD 21678
EXP Realty, LLC
1.37 ACRES
$59,000
Old Morgnec Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
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Off Market Homes Near Gateway Dr

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SOLD
JUL 31, 2026
$195,000
3 bd
1 ba
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
SOLD
JUL 30, 2026
$300,000
4 bd
2 ba
1,325 sqft
304 Hadaway Dr,
Chestertown, MD 21620
Redfin Corporation
SOLD
JUL 29, 2026
$640,000
4 bd
2.5 ba
3,248 sqft
7844 Chester Ct,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUL 22, 2026
$365,000
3 bd
2 ba
1,934 sqft
521 N Kent St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
JUL 21, 2026
$215,000
3 bd
1 ba
1,373 sqft
100 Prospect St,
Chestertown, MD 21620
Real Broker, LLC
SOLD
JUL 20, 2026
$745,000
4 bd
4 ba
3,180 sqft
11122 Boyer Ln,
Worton, MD 21678
TTR Sotheby's International Realty
SOLD
JUL 16, 2026
$435,000
3 bd
2.5 ba
1,784 sqft
215 Fairview Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
SOLD
JUL 14, 2026
$453,000
3 bd
2.5 ba
2,060 sqft
704 Truslow Rd,
Chestertown, MD 21620
RE/MAX Executive
SOLD
JUL 13, 2026
$228,000
3 bd
1.5 ba
2,260 sqft
221 Dutchess Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUL 10, 2026
$42,500
1 ba
1,025 sqft
10199 Augustine Herman Hwy,
Chestertown, MD 21620
See more homes for sale in
Chestertown
Take a look

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Gateway Dr
Chestertown, MD 21620