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

UNDER CONTRACT

0.27 ACRES

103 Maple Ave
Chestertown, MD 21620

4 Beds
2.5 Baths
4,536 sqft (on 0.27 acres)

$615,000

Est. Mortgage $3,538/mo*

Get Pre-Qualified

$615,000

Est. Mortgage $3,538/mo*

Get Pre-Qualified

4 Beds

2.5 Baths

4,536 sqft

(on 0.27 acres)

Local Information

Map ViewExplore the area around 103 Maple Ave.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District. **Interior professional photos are coming soon and are going to be really special**

Home Highlights

Parking

Open Parking

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

$136

Listed

12 days ago

Home Details for 103 Maple Ave

Interior Features
Interior Details Basement: Full,Interior EntryNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 4536 Square Feet
Appliances & Utilities Appliances: Electric Water Heater
Heating & Cooling Heating: Radiator,OilHas CoolingAir Conditioning: Window Unit(s),ElectricHas HeatingHeating Fuel: Radiator
Fireplace & Spa Number of Fireplaces: 6Has a Fireplace
Levels, Entrance, & Accessibility Stories: 4Levels: FourAccessibility: Other
View Has a ViewView: River

Exterior Features
Exterior Home Features Other Structures: Above Grade, Below GradeFoundation: PermanentNo Private Pool
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway
Pool Pool: None
Frontage Waterfront: RiverNot on Waterfront
Water & Sewer Sewer: Public SewerWater Body: Chester River
Finished Area Finished Area (above surface): 4536 Square Feet

Days on Market
Days on Market: 12

Property Information
Year Built Year Built: 1890
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Victorian
Building Construction Materials: BrickNot a New Construction
Property Information Parcel Number: 1504018826

Price & Status
Price List Price: $615,000Price Per Sqft: $136
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE UNDER CONTRACT

Location
Direction & Address City: CHESTERTOWNCommunity: Chestertown Historic District
School Information Elementary School District: Kent County Public SchoolsJr High / Middle School District: Kent County Public SchoolsHigh School District: Kent County Public Schools

Agent Information
Listing Agent Listing ID: MDKE2006676

Building
Building Details Builder Name: H.M. Stuart
Building Area Building Area: 6434 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 0.27 acres

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To Sell

Business
Business Information Ownership: Fee Simple

Miscellaneous
BasementMls Number: MDKE2006676Municipality: ChestertownZillow Contingency Status: Under ContractWater ViewWater View: RiverAbove Grade Unfinished Area: 4536

Additional Information
Source Internet Entire Listing Display: Y

Last check for updates: about 5 hours ago

Listing courtesy of Murphy ONeill, (443) 480-4275

Coldwell Banker Chesapeake Real Estate Company, (410) 778-0330

Source: Bright MLS, MLS#MDKE2006676

Also Listed on Bright MLS.

Market trends in Chestertown

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Price History for 103 Maple Ave

Date	Price	Event	Source
06/29/2026	$615,000	Contingent	Bright MLS #MDKE2006676

06/27/2026	$615,000	Listed For Sale	Bright MLS #MDKE2006676

03/11/1996	$205,000	Sold	N/A
Recording Date 03/11/1996 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax
Assessment	$708,400

Home facts updated by county records

Comparable Sales for 103 Maple Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
119 High St, Chestertown, MD	0.18	Single-Family Home	$1,165,000	12/01/25	5	4.5	4,409
515 N Kent St, Chestertown, MD	0.37	Single-Family Home	$495,000	04/17/26	4	2.5	2,220
200 Washington Ave, Chestertown, MD	0.38	Single-Family Home	$650,000	03/10/26	4	3.5	2,917
201 Radcliffe Dr, Chestertown, MD	0.48	Single-Family Home	$795,000	11/07/25	4	2.5	2,736
217 Philosophers Ter, Chestertown, MD	0.41	Single-Family Home	$370,000	05/01/26	3	1.5	1,404
221 Richard Dr, Chestertown, MD	0.37	Single-Family Home	$398,000	10/24/25	2	2.5	1,711
206 Barroll Dr, Chestertown, MD	0.46	Single-Family Home	$438,000	09/30/25	3	2	1,820

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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 103 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

Murphy ONeill, Coldwell Banker Chesapeake Real Estate Company, (410) 778-0330

Agent Phone: (443) 480-4275

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

103 Maple Ave, Chestertown, MD 21620 is a 4 bedroom, 3 bathroom, 4,536 sqft single-family home built in 1890. This property is currently available for sale and was listed by Bright MLS on Jun 15, 2026. The MLS # for this home is MLS# MDKE2006676.

103 Maple Ave Chestertown, MD 21620

$615,000

$615,000

Local Information

Description

Home Highlights

Home Details for 103 Maple Ave

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

Community

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Market trends in Chestertown

Price History for 103 Maple Ave

Similar Homes You May Like

New Listings near 103 Maple Ave

Property Tax and Assessment

Comparable Sales for 103 Maple Ave

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Chestertown

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

103 Maple Ave
Chestertown, MD 21620