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

301 Maple Ave
Chestertown, MD 21620

Studio
1,605 sqft

$414,000

Trulia Estimate

as of Jul 24, 2026

Est. Refi. Payment $2,420/mo*

Refinance Your Home

$414,000

Trulia Estimate

as of Jul 24, 2026

Est. Refi. Payment $2,420/mo*

Refinance Your Home

Studio

1,605 sqft

Local Information

Map ViewExplore the area around 301 Maple Ave.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1983

Living Area

1,605 sqft

Price/Sqft

$258

About this House

This single-family home is located at 301 Maple Ave, Chestertown, MD. 301 Maple Ave is in Chestertown, MD and in ZIP code 21620. This property has approximately 1,605 sqft of floor space. This property has a lot size of 10016 sqft and was built in 1983.

301 Maple Ave, Chestertown, MD 21620 is a studio, 1,605 sqft single-family home built in 1983. It last sold for $211,150 on Dec 2, 1991. It is currently off market. The Trulia Estimate is $414,000, with a rent estimate of $2,404/month.

Home Details for 301 Maple Ave

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

Exterior Features
Exterior Home Features Roof: CompositionExterior: Brick

Property Information
Year Built Year Built: 1983
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 10016 sqft

Price History for 301 Maple Ave

Date	Price	Event	Source
12/02/1991	$211,150	Sold	N/A
Recording Date 12/02/1991 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

—

Price per sq ft

—

Available listings

5MoM

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Property Tax and Assessment

Year	2025
Tax	$7,015
Assessment	$223,800

Home facts updated by county records

Comparable Sales for 301 Maple Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
110 Philosophers Ter, Chestertown, MD	0.10	Single-Family Home	$175,000	07/25/25	2	1	896
217 Philosophers Ter, Chestertown, MD	0.28	Single-Family Home	$370,000	05/01/26	3	1.5	1,404
211 Richard Dr, Chestertown, MD	0.29	Single-Family Home	$327,500	03/04/26	3	2	1,598
303 E Campus Ave, Chestertown, MD	0.40	Single-Family Home	$364,000	01/16/26	3	2	1,532
221 Richard Dr, Chestertown, MD	0.39	Single-Family Home	$398,000	10/24/25	2	2.5	1,711
104 N Water St, Chestertown, MD	0.21	Single-Family Home	$695,000	01/16/26	4	2	2,522
100 Prospect St, Chestertown, MD	0.37	Single-Family Home	$215,000	07/21/26	3	1	1,373
200 Washington Ave, Chestertown, MD	0.20	Single-Family Home	$650,000	03/10/26	4	3.5	2,917
110 S Mill St, Chestertown, MD	0.24	Single-Family Home	$695,000	11/05/25	3	3.5	2,492
349 High St, Chestertown, MD	0.20	Single-Family Home	$355,000	06/03/26		3	3,664

Nearby homes

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

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OFF MARKET
Est. $177,700
2 bd
1 ba
896 sqft
110 Philosophers Ter,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
Est. $641,600
4 bd
5 ba
3,497 sqft
128 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $505,400
2 bd
1.5 ba
1,416 sqft
106 Church Aly,
Chestertown, MD 21620
Rock Hall Properties Real Estate
OFF MARKET
Est. $969,300
5 bd
5.5 ba
3,756 sqft
212 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $433,000
2 bd
1.5 ba
1,058 sqft
104 Church Aly,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
Est. $371,100
1 bd
1 ba
744 sqft
117 Court St,
Chestertown, MD 21620
Maryland Heritage Properties
OFF MARKET
Est. $585,300
3 bd
2.5 ba
2,296 sqft
129 N Queen St,
Chestertown, MD 21620
Select Land & Homes, LLC
OFF MARKET
Est. $546,200
4 bd
2 ba
2,328 sqft
209 N Queen St,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $670,600
4 bd
2 ba
2,244 sqft
207 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $426,100
5 bd
3.5 ba
2,890 sqft
204 N Mill St,
Chestertown, MD 21620
TTR Sotheby's International Realty
OFF MARKET
Est. $687,000
2 bd
2.5 ba
1,945 sqft
213 N Queen St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
Est. $611,100
5 bd
2.5 ba
2,536 sqft
108 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company

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Additional Cost

Assigned Schools

These are the assigned schools for 301 Maple Ave.

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
200 Morgnec Rd #776f18ccb,
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
101 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
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
501 E Campus Ave #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
103 Hawkins Dr #776f18ccb,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
PET FRIENDLY
$1,920/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
Take a look

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Explore by feature - Pet Friendly

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
$1,920/mo
2 bd
2 ba
900 sqft
104 Maple Ave #4,
Chestertown, MD 21620
PET FRIENDLY
$1,920/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
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

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
$2,000/mo
3 bd
2 ba
960 sqft
129A Manor Ave,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620

Homes for sale near 301 Maple Ave

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$419,999
4 bd
2 ba
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
0.34 ACRES
$380,000
4 bd
2 ba
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OPEN SAT, 10-12PM
$829,000
3 bd
3.5 ba
2,472 sqft
106 S Queen St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
$515,000
2 bd
2.5 ba
1,476 sqft
101 S Mill St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$350,000
2 bd
3 ba
1,518 sqft
522 High St,
Chestertown, MD 21620
Benson & Mangold, LLC
$90,000
2 bd
1 ba
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
$69,900
3 bd
1.5 ba
2,210 sqft
110 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
$1,245,500
5 bd
4.5 ba
3,243 sqft
105 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 301 Maple Ave

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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 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
JUN 29, 2026
$460,000
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
SOLD
JUN 26, 2026
$270,000
136 Prospect St,
Chestertown, MD 21620
SOLD
JUN 26, 2026
$525,000
3 bd
2 ba
1,817 sqft
1014 Twin Ct,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
JUN 26, 2026
$410,000
3 bd
2.5 ba
1,216 sqft
109 S College Ave,
Chestertown, MD 21620
Taylor Properties
SOLD
JUN 25, 2026
$395,000
3 bd
2 ba
1,440 sqft
8629 Airy Hill Rd,
Chestertown, MD 21620
Keller Williams Realty
See more homes for sale in
Chestertown
Take a look

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301 Maple Ave
Chestertown, MD 21620

$414,000

$414,000