Save Search

Price

Beds

Baths

Filters 1

Reset

1 Filter Applied

Basic Info

Price

Beds

Baths

Property Type

Listing Status

Purchase Type

Days On Site

Advanced

Less Than

Unit Level

City Limits Y/N

Property Details

SqFt

Switch to Acre

Lot Size

Switch to Acre

Price per Sqft

Monthly HOA Fee

Year Built

Stories

Kitchens

Flooring

Special Listing Condition

Pool

HOA Y/N

Amenities

Acceptable Financing

Level(s)

Fence

Property Sub Type

Ownership

Adult Community

Basement

Elevator

Exterior Finish

Financing

Other Rooms

Acres

Style

Water Front Y/N

Foundation

Full Bathrooms

Half Bathrooms

Area

Minimum Lease Period

Horse Property

Frontage

Pet Allowed

Property Condition

Water Access

New Construction Y/N

Utilities

Tax Amount

Short Sale(Y/N)

Architectural Style

Sewage Type

Water

Laundry

Roof

Building Type

Unit Features

Basement(Y/N)

Outbuilding

Room Level

Land Lease Fee

Fireplace Y/N

Keyword

Maintenance Fee

Farm Description

Flood Zone

Assessed Value

Interior Features

Fireplace Type

Heating

Cooling

Interior Lot Features

Fireplace Number

Exterior Features

Lot Description

Parking Type

Parking Space

Garage Space

Carport Spaces

Pool Y/N

Garage Y/N

Patio and Porch Features

Property Features

Waterfront

Community Features

Water View

Open House

Has Picture

New

Hot

Virtual Tour

3D Tour

Price Reduced

Save Search (2)

28 Properties

28 Properties Available In 21620

Name: Open House - 10AM-12PM
Start: 2025-08-29T10:00:00.000Z
End: 2025-08-29T12:00:00.000Z
Location: 105 HIGH ST, Chestertown, MD 21620

Default

MD >21620 >

Market Insights

Open Sat 10AM-12PM

$1,245,500

105 HIGH ST, Chestertown, MD 21620

5 Beds5 Baths3,243 SqFt

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

New

$750,000

216 BIRCH RUN RD, Chestertown, MD 21620

3 Beds3 Baths2,176 SqFt

MLS# MDKE2006896

Listed by TTR Sotheby's International Realty

Coming Soon

$304,000

7464 SHORTALL ST, Chestertown, MD 21620

3 Beds2 Baths1,232 SqFt

MLS# MDKE2006988

Listed by Chesapeake Real Estate Associates, LLC

New

$299,900

124 WILTON RD, Chestertown, MD 21620

3 Beds1 Bath1,056 SqFt

MLS# MDQA2018272

Listed by Doug Ashley Realtors, LLC

7982 RADCLIFFE RD, Chestertown, MD 21620

Active

$478,000

7982 RADCLIFFE RD, Chestertown, MD 21620

2 Beds2 Baths1,904 SqFt

MLS# MDKE2006950

Listed by Doug Ashley Realtors, LLC

Under Contract

$349,000

123 HEATH RD, Chestertown, MD 21620

3 Beds2 Baths1,792 SqFt

MLS# MDQA2017994

Listed by Chesapeake Real Estate Associates, LLC

Under Contract

$240,000

107 CONLEY DR, Chestertown, MD 21620

3 Beds1 Bath1,140 SqFt

MLS# MDKE2006828

Listed by Benson & Mangold, LLC

21324 PERSIMMON DR, Chestertown, MD 21620

Price Dropped by $10K

$189,000

21324 PERSIMMON DR, Chestertown, MD 21620

2 Beds1 Bath1,232 SqFt

MLS# MDKE2006816

Listed by Benson & Mangold, LLC

Under Contract

$735,000

210 N QUEEN ST, Chestertown, MD 21620

4 Beds3 Baths2,730 SqFt

MLS# MDKE2006744

Listed by Coldwell Banker Chesapeake Real Estate Company

Active

$325,000

200 MANOR AVE, Chestertown, MD 21620

4 Beds2 Baths2,198 SqFt

MLS# MDKE2006808

Listed by TTR Sotheby's International Realty

105 N WATER ST #2, Chestertown, MD 21620

Under Contract

$475,000

105 N WATER ST #2, Chestertown, MD 21620

2 Beds2 Baths1,011 SqFt

MLS# MDKE2006680

Listed by Northrop Realty

25750 COLLINS AVE, Chestertown, MD 21620

Price Dropped by $20K

$448,000

25750 COLLINS AVE, Chestertown, MD 21620

3 Beds2 Baths3,262 SqFt

MLS# MDKE2006546

Listed by Doug Ashley Realtors, LLC

Under Contract

$515,000

101 S MILL ST, Chestertown, MD 21620

2 Beds3 Baths1,476 SqFt

MLS# MDKE2006674

Listed by Coldwell Banker Chesapeake Real Estate Company

8796 MARYLAND PKWY, Chestertown, MD 21620

Price Dropped by $155K

$1,495,000

8796 MARYLAND PKWY, Chestertown, MD 21620

9 Beds7 Baths4,776 SqFt

MLS# MDKE2006596

Listed by Coldwell Banker Chesapeake Real Estate Company

Active

$380,000

213 BYFORD DR, Chestertown, MD 21620

4 Beds2 Baths1,277 SqFt

MLS# MDKE2006026

Listed by Doug Ashley Realtors, LLC

956 WASHINGTON AVE, Chestertown, MD 21620

Price Dropped by $10K

$275,000

956 WASHINGTON AVE, Chestertown, MD 21620

3 Beds1 Bath1,248 SqFt

MLS# MDKE2006394

Listed by Doug Ashley Realtors, LLC

Under Contract

$365,000

240 MERGANSER DR, Chestertown, MD 21620

3 Beds2 Baths1,120 SqFt

MLS# MDQA2016900

Listed by Chesapeake Real Estate Associates, LLC

Active

$550,000

103 SUTTON WAY, Chestertown, MD 21620

5 Beds4 Baths3,816 SqFt

MLS# MDKE2006344

Listed by TTR Sotheby's International Realty

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

Price Dropped by $100K

$1,500,000

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

7 Beds5 Baths5,400 SqFt

MLS# MDKE2006158

Listed by TTR Sotheby's International Realty

117 WATER ST N #1A, Chestertown, MD 21620

Active

$685,000

117 WATER ST N #1A, Chestertown, MD 21620

3 Beds3 Baths3,000 SqFt

MLS# MDKE2006162

Listed by TTR Sotheby's International Realty

117 WATER ST N #2A, Chestertown, MD 21620

Active

$375,000

117 WATER ST N #2A, Chestertown, MD 21620

2 Beds1 Bath787 SqFt

MLS# MDKE2006166

Listed by TTR Sotheby's International Realty

117 WATER ST N #2B, Chestertown, MD 21620

Active

$350,000

117 WATER ST N #2B, Chestertown, MD 21620

1 Bed1 Bath850 SqFt

MLS# MDKE2006168

Listed by TTR Sotheby's International Realty

117 WATER ST N #1B, Chestertown, MD 21620

Active

$200,000

117 WATER ST N #1B, Chestertown, MD 21620

1 Bed1 Bath700 SqFt

MLS# MDKE2006164

Listed by TTR Sotheby's International Realty

204 DOUBLE CREEK RD, Chestertown, MD 21620

Price Dropped by $20K

$545,000

204 DOUBLE CREEK RD, Chestertown, MD 21620

3 Beds3 Baths2,927 SqFt

MLS# MDQA2015996

Listed by Doug Ashley Realtors, LLC

Basic Info

Property Details

Interior Features

Exterior Features

Property Features

28 Properties Available In 21620

explore listings in 21620