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$284,900 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,900 Sq. Ft.
  • 1 Car Garage
  • Updated 2 days ago
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Welcome to this three-level, interior-unit townhome in the desirable Oak Hollow community of Chestertown. Conveniently located near shopping, schools, the YMCA, and historic downtown, this home offers comfortable living and low-maintenance convenience. The entry level features a one-car garage and a flexible bonus room ideal for a home office, gym, or recreation space with walk-out access to the rear yard. The main level includes a spacious living room, half bath, and an eat-in kitchen with pantry storage and adjoining dining area. Step outside to the rear deck overlooking a peaceful wooded backdrop. The upper level offers three bedrooms, including a primary suite with a private bath, plus a full hall bath and conveniently located laundry area. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment property, this Oak Hollow townhome is ready for its next owner.

Full Property Details for 104 Acorn Dr

General

  • Price: $284,900
  • HOA FEE: $55/month
  • Taxes: $3,059 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006668
  • Updated: 6/12/2026
  • Added to Site: 2 day(s) ago

Interior

  • Appliances: Dishwasher, Washer/Dryer Stacked, Oven/Range - Electric, Refrigerator
  • Flooring: Carpet, Laminated

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 1
  • Parking Features: Concrete Driveway
  • Parking Type: Attached Garage
  • Garage Description: Garage - Front Entry, Garage Door Opener

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: OAK HOLLOW
  • Driving Directions: GPS
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Septic
  • Water: Public

Structural Information

  • Architectural Style: Traditional, Unit/Flat
  • Structure Type: Interior Row/Townhouse
  • Construction: Vinyl Siding
  • Foundation: Block
  • Roof: Shingle
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 1,900
  • Sq. Ft. Source: Assessor
  • Living Area: 1,900 Sq. Ft.
  • Finished Above Grnd: 1,900 Sq. Ft.
  • Year Built: 2004
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.05
  • Lot Size (Sq. Ft.): 2,119
  • Lot Size Source: Assessor
  • Zoning: R3/R4
  • Lot Description: Backs - Open Common Area

Financial Considerations

  • Price Per Sq. Ft.: $149.95
  • Association Fee: $55
  • Assoc Fee Freq.: Monthly
  • Assessment Year: 2026
  • City/TownTax: $845
  • City/TownTax Freq: Annually
  • County Tax: $2,214
  • County Tax Freq: Annually
  • Tax w/Assessment: $197,567
  • Tax Amount: $3,059
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1900

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 9

Listed by Cross Street Realtors LLC, Sarah E. King

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Listing agent

— 104 Acorn Dr —

  • Sarah E. King

    Cross Street Realtors LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 104 Acorn Dr

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-51 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.7 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-124.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 104 Acorn Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/12/2026
Listed
$284,900
46.38%
MLS
10/13/2004
Sold
$194,625
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 104 Acorn Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,059
5%
$195,200
5%
2024
$2,916
12%
$186,067
5%
2023
$2,613
—
$176,933
5%
2022
$2,613
-1%
$167,800
—
2020
$2,630
—
$167,800
—
2021
$2,630
-2%
$167,800
-2%
2020
$2,692
4%
$172,100
3%
2019
$2,590
7%
$166,667
3%
2018
$2,425
3%
$161,233
3%
2017
$2,343
307%
$155,800
—
2016
$576
-75%
$155,800
—
2015
$2,343
-4%
$155,800
-4%
2014
$2,449
—
$162,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 104 Acorn Dr

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NMLS#: 1598647

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Listed by Cross Street Realtors LLC, Sarah E. King

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104 Acorn Drive, Chestertown, MD 21620 (MLS# MDKE2006668) is a Townhouse property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 104 Acorn Drive is currently listed for $284,900 and was received on June 12, 2026. Want to learn more about 104 Acorn Drive? Do you have questions about finding other Townhouse real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

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