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

108 Maple Ave
Chestertown, MD 21620

5 Beds
2.5 Baths
2,460 sqft (on 19,440 acres)

$534,000

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $3,074/mo*

Refinance Your Home

$534,000

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $3,074/mo*

Refinance Your Home

5 Beds

2.5 Baths

2,460 sqft

(on 19,440 acres)

Local Information

Map ViewExplore the area around 108 Maple Ave.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 108 Maple Ave, Chestertown, MD. 108 Maple Ave is in Chestertown, MD and in ZIP code 21620. This property has 5 bedrooms, 3 bathrooms and approximately 2,460 sqft of floor space. This property has a lot size of 0.45 acres and was built in 1782.

108 Maple Ave, Chestertown, MD 21620 is a 5 bedroom, 3 bathroom, 2,460 sqft single-family home built in 1782. It last sold for $299,000 on Aug 1, 2022. It is currently off market. The Trulia Estimate is $534,000, with a rent estimate of $3,097/month.

Home Highlights

Parking

No Info

Outdoor

Porch, Patio, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 108 Maple Ave

Interior Features
Heating & Cooling Heating: Baseboard, Oil, Propane ButaneAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 3Floors: Hardwood
Interior Details Additional StorageAtticTypes of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, WorkshopStorage
Appliances & Utilities MicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace
Windows, Doors, Floors & Walls Double Paned Windows

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: OtherGardenLawnPatioPorch
Parking & Garage Parking Spaces: 4Parking: Carport

Property Information
Year Built Year Built: 1782
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 19440.00 acres

Price History for 108 Maple Ave

Date	Price	Event	Source
08/01/2022	$299,000	Sold	Bright MLS #MDKE2001584
Recording Date 08/01/2022 County Transfer Tax N/A Total Transfer Tax N/A
07/05/2022	$299,000	Contingent	Bright MLS #MDKE2001584

07/02/2022	$299,000	Listed For Sale	Bright MLS #MDKE2001584

02/16/2022	$329,000	ListingRemoved	Bright MLS #MDKE2000720

12/30/2021	$329,000	Listed For Sale	Bright MLS #MDKE2000720

Market trends in Chestertown

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Skip to last item

Results are loading

Skip to first item

Property Tax and Assessment

Year	2025
Tax	$12,829
Assessment	$409,300

Home facts updated by county records

Comparable Sales for 108 Maple Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
104 N Water St, Chestertown, MD	0.07	Single-Family Home	$695,000	01/16/26	4	2	2,522
211 Richard Dr, Chestertown, MD	0.33	Single-Family Home	$327,500	03/04/26	3	2	1,598
515 N Kent St, Chestertown, MD	0.41	Single-Family Home	$495,000	04/17/26	4	2.5	2,220
200 N Water St, Chestertown, MD	0.08	Single-Family Home	$950,000	04/30/26	4	3	3,034
221 Old Bridge Rd, Chestertown, MD	0.49	Single-Family Home	$359,900	11/24/25	3	2	1,851
101 Birch Run Rd, Chestertown, MD	0.54	Single-Family Home	$475,000	12/11/25	3	2	1,961
206 Barroll Dr, Chestertown, MD	0.49	Single-Family Home	$438,000	09/30/25	3	2	1,820
303 Cedar St, Chestertown, MD	0.72	Single-Family Home	$325,000	01/30/26	3	2.5	2,577
303 E Campus Ave, Chestertown, MD	0.51	Single-Family Home	$364,000	01/16/26	3	2	1,532
221 Richard Dr, Chestertown, MD	0.41	Single-Family Home	$398,000	10/24/25	2	2.5	1,711

Nearby homes

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

Skip to last item

OFF MARKET
Est. $583,300
3 bd
2.5 ba
2,296 sqft
129 N Queen St,
Chestertown, MD 21620
Select Land & Homes, LLC
FOR SALE
3D VIEW
$685,000
3 bd
3 ba
3,000 sqft
117 N Water St #1A,
Chestertown, MD 21620
TTR Sotheby's International Realty
OFF MARKET
Est. $289,400
1 bd
1 ba
652 sqft
117 N Water St #3B,
Chestertown, MD 21620
Gunther-McClary Real Estate
FOR SALE
3D VIEW
$375,000
2 bd
1 ba
787 sqft
117 N Water St #2A,
Chestertown, MD 21620
TTR Sotheby's International Realty
FOR SALE
3D VIEW
$350,000
1 bd
1 ba
850 sqft
117 N Water St #2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
OFF MARKET
Est. $395,900
2 bd
1 ba
729 sqft
117 N Water St #3A,
Chestertown, MD 21620
Gunther-McClary Real Estate
FOR SALE
3D VIEW
$200,000
1 bd
1 ba
700 sqft
117 N Water St #1B,
Chestertown, MD 21620
TTR Sotheby's International Realty
FOR SALE
3D VIEW
$1,600,000
7 bd
5 ba
5,400 sqft
117 N Water St #1A-1B-2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
OFF MARKET
Est. $727,700
4 bd
3.5 ba
2,866 sqft
106 Water 1/2 St N,
Chestertown, MD 21620
Cross Street Realtors LLC
OFF MARKET
Est. $1,145,400
5 bd
3.5 ba
3,030 sqft
109 N Water St,
Chestertown, MD 21620
Select Land & Homes, LLC
OFF MARKET
Est. $646,500
4 bd
5 ba
3,497 sqft
128 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $1,653,400
4 bd
4.5 ba
5,195 sqft
201 N Water St,
Chestertown, MD 21620
Maryland Heritage Properties

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 108 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

Skip to last item

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
200 Clipper Way #776f18ccb,
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
160 Flatland Rd #f320a52c6,
Chestertown, MD 21620
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
103 Hawkins Dr #776f18ccb,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
See more homes for rent in
Chestertown
Take a look

Skip to first item

Explore by feature - Air Conditioning

9 rentals with air conditioning in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$2,075/mo
3 bd
1.5 ba
1,280 sqft
108 Metcalf Rd,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware Ave,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$2,000/mo
3 bd
1 ba
1,122 sqft
351 Calvert St,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$2,075/mo
3 bd
1.5 ba
1,280 sqft
108 Metcalf Rd,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware 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
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Homes for sale near 108 Maple Ave

Skip to last item

COMING SOON 7/17
0.46 ACRES
$735,000
4 bd
2.5 ba
2,730 sqft
210 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$865,000
3 bd
3.5 ba
2,472 sqft
106 S Queen St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.34 ACRES
$380,000
4 bd
2 ba
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$1,245,500
5 bd
4.5 ba
3,243 sqft
105 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$419,999
4 bd
2 ba
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
$515,000
2 bd
2.5 ba
1,476 sqft
101 S Mill St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$89,900
3 bd
1.5 ba
2,210 sqft
110 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
$399,900
2 bd
3 ba
1,518 sqft
522 High St,
Chestertown, MD 21620
Benson & Mangold, LLC
See more homes for sale in
Chestertown
Take a look

Skip to first item

Off Market Homes Near 108 Maple Ave

Skip to last item

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
$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
SOLD
JUN 24, 2026
$270,000
134 Prospect St,
Chestertown, MD 21620
SOLD
JUN 23, 2026
$485,000
1 ba
2,258 sqft
504 Washington Ave,
Chestertown, MD 21620
SOLD
JUN 17, 2026
$325,000
3 bd
1 ba
1,427 sqft
202 Valley Rd,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
JUN 8, 2026
$293,000
3 bd
2 ba
1,152 sqft
301 Lincoln Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
JUN 5, 2026
$660,000
3 bd
2 ba
1,600 sqft
118 Little Harbor Way #202,
Chestertown, MD 21620
Benson & Mangold, LLC
SOLD
JUN 4, 2026
$290,000
2 bd
2.5 ba
1,864 sqft
115 Acorn Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
See more homes for sale in
Chestertown
Take a look

Skip to first item

108 Maple Ave
Chestertown, MD 21620

$534,000

$534,000

Local Information