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

FOR SALE

0.41 ACRES

304 Hadaway Dr
Chestertown, MD 21620

4 Beds
2 Baths
1,325 sqft (on 0.41 acres)

$339,000

Est. Mortgage $1,910/mo*

Get Pre-Qualified

$339,000

Est. Mortgage $1,910/mo*

Get Pre-Qualified

4 Beds

2 Baths

1,325 sqft

(on 0.41 acres)

Local Information

-- mins to

Commute Destination

Description

Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a perfectly sized dining room and conveniently placed laundry center. The kitchen is absolutely stunning, with stainless Steele appliances, granite countertops, 42" cabinets and new hardwood floors. Moving into the large primary en suit bedroom, you will fall in love with the spa like bath with a large granite vanity, custom tiled stand up shower and tile floors. The home has a brand new 30 year architectural shingle roof, new windows, furnace, water heater, flush mount lights and the whole house has been painted on the interior and exterior with Sherwin Williams designer color collection. Enjoy the large and lush front and back yards, and large driveway. All within walking distance to Washington College and the beautiful and historic town of Chestertown.

Home Highlights

Parking

4 Open Spaces

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

$256

Listed

73 days ago

Home Details for 304 Hadaway Dr

Interior Features
Interior Details Number of Rooms: 9Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bathroom 1, Bathroom 2, Dining Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 4Main Level Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout Living Area: 1325 Square Feet
Appliances & Utilities Utilities: Above GroundAppliances: Water Heater, Dishwasher, Refrigerator, Cooktop, Washer/Dryer Stacked, Disposal, MicrowaveDishwasherDisposalLaundry: Main LevelMicrowaveRefrigerator
Heating & Cooling Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa No Fireplace
Gas & Electric Electric: 220 Volts
Windows, Doors, Floors & Walls Door: Insulated, Six PanelFlooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility Stories: 1Levels: OneAccessibility: NoneFloors: Ceramic Tile, Hardwood
View Has a ViewView: Street
Security Security: Main Entrance Lock

Exterior Features
Exterior Home Features Roof: Architectural ShingleOther Structures: Above Grade, Below GradeExterior: Lighting, Play Area, SidewalksFoundation: Concrete Perimeter, PermanentNo Private Pool
Parking & Garage Open Parking Spaces: 4No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Driveway,Private,Surface
Pool Pool: None
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1325 Square Feet

Days on Market
Days on Market: 73

Property Information
Year Built Year Built: 1960Year Renovated: 2025
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building Construction Materials: OtherNot a New Construction
Property Information Condition: ExcellentParcel Number: 1504004752

Price & Status
Price List Price: $339,000Price Per Sqft: $256
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

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

Agent Information
Listing Agent Listing ID: MDKE2006116

Building
Building Area Building Area: 1325 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 0.41 acres

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Agency

Business
Business Information Ownership: Fee Simple

Miscellaneous
Mls Number: MDKE2006116Municipality: ChestertownAbove Grade Unfinished Area: 1325

Additional Information
Source Internet Entire Listing Display: Y

Last check for updates: about 13 hours ago

Listing courtesy of Greg Morris, (443) 956-4171

Cummings & Co. Realtors, (410) 823-0033

Listing Team: Greg Morris Team

Source: Bright MLS, MLS#MDKE2006116

Also Listed on Bright MLS.

Price History for 304 Hadaway Dr

Date	Price	Event	Source
04/03/2026	$339,000	Listed For Sale	Bright MLS #MDKE2006116

03/16/2026	$344,900	ListingRemoved	Bright MLS #MDKE2006116

03/06/2026	$344,900	PendingToActive	Bright MLS #MDKE2006116

02/24/2026	$344,900	Pending	Bright MLS #MDKE2006116

02/12/2026	$344,900	PriceChange	Bright MLS #MDKE2006116
Price Change $342,400 (13,696%)
02/11/2026	$2,500	ListingRemoved	Zillow Rentals

02/09/2026	$2,500	Listed For Rent	Zillow Rentals

01/07/2026	$350,000	PriceChange	Bright MLS #MDKE2005848
Price Change $49,000 (-12%)
11/29/2025	$399,000	PriceChange	Bright MLS #MDKE2005848
Price Change $26,000 (-6%)
11/07/2025	$425,000	Listed For Sale	Bright MLS #MDKE2005848

07/31/2025	$250,000	Sold	Bright MLS #MDKE2005430
Recording Date 07/31/2025 County Transfer Tax N/A Total Transfer Tax N/A
07/19/2025	$249,900	Pending	Bright MLS #MDKE2005430

07/12/2025	$249,900	Listed For Sale	Bright MLS #MDKE2005430

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Property Tax and Assessment

Year	2025
Tax	$5,106
Assessment	$163,400

Home facts updated by county records

Comparable Sales for 304 Hadaway Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
306 Cedar St, Chestertown, MD	0.33	Single-Family Home	$312,000	06/13/25	4	2	1,404
205 Pine St, Chestertown, MD	0.22	Single-Family Home	$296,337	09/30/25	3	1.5	2,212
204 Rolling Rd, Chestertown, MD	0.27	Single-Family Home	$340,000	03/19/26	3	2	2,296
224 Valley Rd, Chestertown, MD	0.28	Single-Family Home	$455,000	10/21/25	3	2	1,886
411 Greenwood Ave, Chestertown, MD	0.19	Single-Family Home	$415,000	01/07/26	3	2.5	1,676
303 E Campus Ave, Chestertown, MD	0.50	Single-Family Home	$364,000	01/16/26	3	2	1,532
126 Metcalf Rd, Chestertown, MD	0.24	Single-Family Home	$230,000	11/20/25	3	2	1,140

Assigned Schools

These are the assigned schools for 304 Hadaway 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

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
4y ago
"Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
1
Flag
Trulia User
Prev. Resident
4y 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
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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
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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.
11y 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

Additional Cost

Greg Morris, Cummings & Co. Realtors, (410) 823-0033

Agent Phone: (443) 956-4171

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

304 Hadaway Dr, Chestertown, MD 21620 is a 4 bedroom, 2 bathroom, 1,325 sqft single-family home built in 1960. This property is currently available for sale and was listed by Bright MLS on Apr 3, 2026. The MLS # for this home is MLS# MDKE2006116.

304 Hadaway Dr Chestertown, MD 21620

$339,000

$339,000

Local Information

Description

Home Highlights

Home Details for 304 Hadaway Dr

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

Price History for 304 Hadaway Dr

Similar Homes You May Like

New Listings near 304 Hadaway Dr

Property Tax and Assessment

Comparable Sales for 304 Hadaway Dr

Assigned Schools

What Locals Say about Chestertown

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Additional Cost

304 Hadaway Dr
Chestertown, MD 21620