Recently Viewed Properties
See This Home
Save This Listing
Close

$440,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1,058 Sq. Ft.
  • Updated 1 day ago
See This Home
Save This Home
See This Home
Save This Home
A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

Full Property Details for 104 Church Alley

General

  • Price: $440,000
  • Taxes: $3,471 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006900
  • Updated: 8/20/2026
  • Added to Site: 1 day(s) ago

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 2
  • Bedrooms Upper: 2

Other Rooms

  • Laundry: Main Floor

Exterior

  • Porch/Patio/Deck: Deck(s)

Parking

  • Parking Features: Free
  • Parking Type: On Street

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: CHESTERTOWN HISTORIC DISTRICT
  • Cross Streets: Court St
  • Driving Directions: From High St, turn onto Court St. Right on Church Alley. Property will be on the left.
  • Location Details: Downtown
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Heating & Cooling

  • Cooling Type: Ductless/Mini-Split
  • Cooling Fuel: Electric
  • Heating Type: Zoned
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Other
  • Structure Type: Twin/Semi-Detached
  • Construction: Frame
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Outside Entrance, Partial, Dirt Floor
  • Foundation: Brick/Mortar
  • Roof: Metal
  • Walls/Ceilings: Dry Wall
  • Stories Description: Main, Upper 1
  • Square Feet: 1,058
  • Sq. Ft. Source: Assessor
  • Living Area: 1,058 Sq. Ft.
  • Finished Above Grnd: 1,058 Sq. Ft.
  • Year Built: 1880
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Property View: Courtyard, Street
  • Lot Size (Acres): 0.04
  • Lot Size (Sq. Ft.): 1,800
  • Lot Size Source: Assessor
  • Zoning: RB
  • Fencing (Description): Picket, Fully

Financial Considerations

  • Price Per Sq. Ft.: $415.88
  • Assessment Year: 2026
  • City/TownTax: $959
  • City/TownTax Freq: Annually
  • County Tax: $2,512
  • County Tax Freq: Annually
  • Tax w/Assessment: $283,500
  • Tax Amount: $3,471
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1058

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 104 Church Alley —

  • Peter D Heller

    Coldwell Banker Chesapeake Real Estate Company

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 Church Alley

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-50.4 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.6 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-125.4 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 Church Alley Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/20/2026
Listed
$440,000
6.67%
MLS
1/12/2024
Sold
$412,500
—
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 Church Alley

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,471
—
$283,500
28%
2025
$3,471
—
$221,500
—
2024
$3,471
-12%
$221,500
—
2023
$3,954
—
$221,500
-13%
2022
$3,954
58%
$253,900
65%
2020
$2,508
—
$153,800
-4%
2021
$2,508
—
$160,000
—
2020
$2,502
1%
$160,000
—
2019
$2,486
-2%
$160,000
-5%
2018
$2,540
—
$168,900
—
2017
$2,540
306%
$168,900
—
2016
$625
-77%
$168,900
-5%
2015
$2,667
100%
$177,300
—
2014
$1,333
—
$177,300
—
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 Church Alley

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller

Similar Properties near 104 Church Alley

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

25750 Collins Ave, Chestertown, MD 21620 - Photo 1 Price Reduced
-$20,000 (-4.27%)
$448,000

25750 Collins Ave  Chestertown, MD 21620

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 3,262
    Sq. Ft.
Listed by Doug Ashley Realtors, LLC, Grace M Crockett
414 Church St, Sudlersville, MD 21668 - Photo 1 Just Listed
$435,000

414 Church St  Sudlersville, MD 21668

  • Single Family
  • Active
  • Updated 21 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,568
    Sq. Ft.
Listed by Lisa Knotts (302) 362-6365
11944 Augustine Herman Hwy, Kennedyville, MD 21645 - Photo 1
$430,000

11944 Augustine Herman Hwy  Kennedyville, MD 21645

  • Single Family
  • Active
  • 4
    Beds
  • 2
    Total Baths
  • 2,604
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, William Sutton and Coldwell Banker Chesapeake Real Estate Company, Lacey R Sutton

Just Listed near 104 Church Alley

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

10725 Worton Rd, Worton, MD 21678 - Photo 1 Just Listed
$349,000

10725 Worton Rd  Worton, MD 21678

  • Single Family
  • Active
  • Updated 19 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,089
    Sq. Ft.
Listed by Select Land & Homes, LLC, Hayley A Norris and Select Land & Homes, LLC, William H Norris III
334 Eagle Manor Dr, Church Hill, MD 21623 - Photo 1 Just Listed
$599,964
Open House

334 Eagle Manor Dr  Church Hill, MD 21623

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,016
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Lucy Rose and Long & Foster Real Estate, Inc., Mary Elizabeth Jameson
224 Ewingtown Rd, Church Hill, MD 21623 - Photo 1 Just Listed
$395,000

224 Ewingtown Rd  Church Hill, MD 21623

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 2,448
    Sq. Ft.
Listed by Doug Ashley Realtors, LLC, Debra B Meikle
458 Eagle Manor Dr, Church Hill, MD 21623 - Photo 1 Just Listed
$695,000
Open House

458 Eagle Manor Dr  Church Hill, MD 21623

  • Single Family
  • Active
  • Updated 15 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,456
    Sq. Ft.
Listed by Clark & Co Realty, LLC, Karen T Clark

Price Reduced near 104 Church Alley

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

11167 Oak Ln, Worton, MD 21678 - Photo 1 Price Reduced
-$18,600 (-6.45%)
$269,900

11167 Oak Ln  Worton, MD 21678

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 960
    Sq. Ft.
Listed by Chesapeake Real Estate Associates, LLC, Martine H McGinty
14136 Kentmore Park Rd, Kennedyville, MD 21645 - Photo 1 Price Reduced
-$16,000 (-3.11%)
$499,000

14136 Kentmore Park Rd  Kennedyville, MD 21645

  • Single Family
  • Active
  • Updated 1 hour ago
  • 4
    Beds
  • 2
    Total Baths
  • 3,564
    Sq. Ft.
Listed by Gunther-McClary Real Estate, Patricia L Kern
6022 N Main St, Rock Hall, MD 21661 - Photo 1 Price Reduced
-$10,000 (-3.46%)
$279,000

6022 N Main St  Rock Hall, MD 21661

  • Single Family
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,386
    Sq. Ft.
Listed by Doug Ashley Realtors, LLC, Michele A Palmer
371 Overture Way, Centreville, MD 21617 - Photo 1 Price Reduced
-$24,900 (-3.56%)
$675,000

371 Overture Way  Centreville, MD 21617

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 5
    Total Baths
  • 6,693
    Sq. Ft.
Listed by Robin Maisel (410) 271-1150

Recent Sales near 104 Church Alley

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

515 N Kent St, Chestertown, MD 21620 - Photo 1 Sold
$495,000

515 N Kent St  Chestertown, MD 21620

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,220
    Sq. Ft.
Listed by Cross Street Realtors LLC, Jody Baker
Sold by Benson & Mangold, LLC, Connor LeMire
109 S College Ave, Chestertown, MD 21620 - Photo 1 Sold
$410,000

109 S College Ave  Chestertown, MD 21620

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,432
    Sq. Ft.
Listed by Taylor Properties, Jeff Guthrie
Sold by LPT Realty, LLC, Jordan Evan Larigan
201 Greenwood Ave, Chestertown, MD 21620 - Photo 1 Sold
$495,000

201 Greenwood Ave  Chestertown, MD 21620

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,984
    Sq. Ft.
Listed by Doug Ashley Realtors, LLC, Grace M Crockett
Sold by Cross Street Realtors LLC, Ray Davis
201 Birch Run Rd, Chestertown, MD 21620 - Photo 1 Sold
$430,000

201 Birch Run Rd  Chestertown, MD 21620

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,588
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill
Sold by Blackwell Real Estate, LLC, Christina Cartagirone

104 Church Alley, Chestertown, MD 21620 (MLS# MDKE2006900) is a Single Family property with 2 bedrooms, 1 full bathroom and 1 partial bathroom. 104 Church Alley is currently listed for $440,000 and was received on August 20, 2026. Want to learn more about 104 Church Alley? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

Tour this property