Chestertown, MD Properties

4,426 properties found

Use our free property search to explore residence insights across Chestertown. Whether you’re evaluating opportunities for acquisition, investment, or exploring housing market trends in the city, Chestertown presents a rich mix of property types, from single-family residences and condos to townhomes and multi-family properties. Rew Online allows you to easily analyze local market trends, access property information, and find contact details of property owners for your real estate goals.

The data across Chestertown shows that the median land area across properties amounts to 21,780 square feet. The city includes a total of 4,426 addresses. The typical property construction year is 1974. The median value of buildings is estimated to be $158,500, while the land value equals $90,800. In addition, the middle transfer price of properties in the city is approximately $230,000.

An overview of property financial health shows that the typical current estimated equity balance in Chestertown stands at $266,708. Meanwhile, the median lien balance of houses is $199,125, showing the overall debt secured against residential properties.

When it comes to property characteristics in the city, homes have a median of 3 bedrooms and 2 bathrooms. Bedroom counts range from a minimum of 0 to a maximum of 10, while bathroom counts range from 0 to 13. Approximately 544 properties have a pool, representing 12.29% of all homes citywide. In addition, around 1,850 homes feature a garage, which makes up 41.8% of houses.

Moreover, an address listing may reveal a specific property’s parcel ID, full address, owner name, emails, and phone numbers, which can make it easier to reach out regarding property acquisition or investment opportunities.

Property TypeType
Property ValueValue
BedroomsRooms
All filters
$288K Est. Value

89 Chandler Mountain Rd, Chestertown, MD 03812

2 beds
1 bath
Built: 1975
774 sq ft
13,939 sq ft lot
Last Sale Date

7/25/2014

Est Equity

$292,087 (101%)

Primary Contact
$202K Est. Value

10674 Kasota Rd, Chestertown, MD 20662

Built: 1977
87,120 sq ft lot
Last Sale Date

10/25/2024

Est Equity

$14,687 (7%)

Primary Contact

509 Morgnec Rd, Chestertown, MD 21048

150,718 sq ft lot
Last Sale Date

5/14/2012

Primary Contact
$1.17M Est. Value

22153 1st Point Rd, Chestertown, MD 21620

5 beds
2 baths
Built: 1975
1,354 sq ft
83,200 sq ft lot
Last Sale Date

5/11/1990

Est Equity

$1,120,799 (96%)

Primary Contact
$139K Est. Value

10207 2nd Point Rd, Chestertown, MD 21620

87,120 sq ft lot
Last Sale Date

6/8/2022

Est Equity

$139,405 (100%)

Primary Contact
$1.13M Est. Value

10210 2nd Point Rd, Chestertown, MD 21620

64,904 sq ft lot
Last Sale Date

3/1/2018

Est Equity

$1,133,096 (100%)

Primary Contact
$866K Est. Value

10210 2nd Point Rd, Chestertown, MD 21620

2 baths
Built: 1978
2,698 sq ft
50,094 sq ft lot
Last Sale Date

3/1/2018

Est Equity

$911,488 (105%)

Primary Contact
$637K Est. Value

10020 3rd Point Rd, Chestertown, MD 21620

2 baths
Built: 1997
3,123 sq ft
43,560 sq ft lot
Est Equity

$670,420 (105%)

Primary Contact
$1.45M Est. Value

10080 3rd Point Rd, Chestertown, MD 21620

4 beds
3 baths
Built: 1962
2,858 sq ft
69,696 sq ft lot
Last Sale Date

12/27/2017

Est Equity

$590,151 (41%)

Primary Contact
$1.75M Est. Value

10092 3rd Point Rd, Chestertown, MD 21620

Built: 2010
216,058 sq ft lot
Last Sale Date

1/20/2004

Est Equity

$1,751,484 (100%)

Primary Contact
$464K Est. Value

10099 3rd Point Rd, Chestertown, MD 21620

3 beds
2 baths
Built: 1983
2,098 sq ft
67,082 sq ft lot
Last Sale Date

1/7/2009

Est Equity

$391,551 (84%)

Primary Contact
$495K Est. Value

10099 3rd Point Rd, Chestertown, MD 21620

3 beds
3 baths
Built: 1983
2,098 sq ft
50,530 sq ft lot
Last Sale Date

1/7/2009

Est Equity

$413,063 (83%)

Primary Contact
$1.82M Est. Value

10108 3rd Point Rd, Chestertown, MD 21620

3 baths
Built: 1988
3,921 sq ft
64,469 sq ft lot
Last Sale Date

6/30/2023

Est Equity

$2,012,892 (110%)

Primary Contact
$1.58M Est. Value

10140 3rd Point Rd, Chestertown, MD 21620

4 beds
4 baths
Built: 1960
3,736 sq ft
67,431 sq ft lot
Last Sale Date

6/14/2017

Est Equity

$1,203,570 (76%)

Primary Contact
$880K Est. Value

10141 3rd Point Rd, Chestertown, MD 21620

2 baths
Built: 2000
2,196 sq ft
50,530 sq ft lot
Last Sale Date

4/17/2008

Est Equity

$515,115 (59%)

Primary Contact
$562K Est. Value

10145 3rd Point Rd, Chestertown, MD 21620

3 beds
3 baths
Built: 2000
3,292 sq ft
50,094 sq ft lot
Last Sale Date

8/4/2021

Est Equity

$311,629 (55%)

Primary Contact
$387K Est. Value

10170 3rd Point Rd, Chestertown, MD 21620

2 baths
Built: 1995
1,799 sq ft
64,904 sq ft lot
Last Sale Date

11/1/1991

Est Equity

$372,052 (96%)

Primary Contact
$461K Est. Value

10181 3rd Point Rd, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
2,127 sq ft
44,867 sq ft lot
Last Sale Date

6/30/2022

Est Equity

$173,271 (38%)

Primary Contact
$285K Est. Value

100 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2004
1,930 sq ft
3,762 sq ft lot
Last Sale Date

6/9/2025

Est Equity

$300,822 (105%)

Primary Contact
$293K Est. Value

101 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,864 sq ft
3,905 sq ft lot
Last Sale Date

2/13/2009

Est Equity

$299,819 (102%)

Primary Contact
$280K Est. Value

102 Acorn Dr, Chestertown, MD 21620

2 baths
Built: 2004
1,900 sq ft
2,119 sq ft lot
Last Sale Date

10/27/2004

Est Equity

$276,914 (99%)

Primary Contact
$292K Est. Value

103 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,876 sq ft
2,200 sq ft lot
Last Sale Date

6/24/2016

Est Equity

$145,206 (50%)

Primary Contact
$270K Est. Value

104 Acorn Dr, Chestertown, MD 21620

2 baths
Built: 2004
1,900 sq ft
2,119 sq ft lot
Last Sale Date

11/15/2004

Est Equity

$267,148 (99%)

Primary Contact
$275K Est. Value

105 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,840 sq ft
2,200 sq ft lot
Last Sale Date

11/9/2012

Est Equity

$270,668 (99%)

Primary Contact
$298K Est. Value

106 Acorn Dr, Chestertown, MD 21620

2 baths
Built: 2004
1,900 sq ft
2,119 sq ft lot
Last Sale Date

7/15/2015

Est Equity

$306,661 (103%)

Primary Contact
$303K Est. Value

107 Acorn Dr, Chestertown, MD 21620

2 baths
Built: 2005
1,876 sq ft
2,200 sq ft lot
Last Sale Date

1/8/2009

Est Equity

$156,554 (52%)

Primary Contact
$274K Est. Value

108 Acorn Dr, Chestertown, MD 21620

2 baths
Built: 2004
1,900 sq ft
2,120 sq ft lot
Last Sale Date

11/1/2004

Est Equity

$158,805 (58%)

Primary Contact
$306K Est. Value

109 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,840 sq ft
2,200 sq ft lot
Last Sale Date

7/21/2021

Est Equity

$98,554 (32%)

Primary Contact
$308K Est. Value

110 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2004
1,900 sq ft
2,120 sq ft lot
Last Sale Date

3/31/2022

Est Equity

$134,619 (44%)

Primary Contact
$244K Est. Value

111 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,916 sq ft
2,200 sq ft lot
Last Sale Date

8/31/2020

Est Equity

$167,262 (69%)

Primary Contact
$316K Est. Value

112 Acorn Dr, Chestertown, MD 21620

4 beds
2 baths
Built: 2004
1,930 sq ft
4,663 sq ft lot
Last Sale Date

1/11/2019

Est Equity

$314,374 (100%)

Primary Contact
$300K Est. Value

113 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,864 sq ft
3,300 sq ft lot
Last Sale Date

3/21/2006

Est Equity

$298,886 (100%)

Primary Contact
$300K Est. Value

115 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,864 sq ft
3,300 sq ft lot
Last Sale Date

6/7/2005

Est Equity

$215,396 (72%)

Primary Contact
$287K Est. Value

117 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,876 sq ft
2,200 sq ft lot
Last Sale Date

11/21/2019

Est Equity

$228,878 (80%)

Primary Contact
$277K Est. Value

119 Acorn Dr, Chestertown, MD 21620

2 beds
2 baths
Built: 2005
1,840 sq ft
2,200 sq ft lot
Last Sale Date

2/18/2025

Est Equity

$291,875 (105%)

Primary Contact
$286K Est. Value

121 Acorn Dr, Chestertown, MD 21620

2 beds
2 baths
Built: 2005
1,876 sq ft
2,200 sq ft lot
Last Sale Date

6/10/2005

Est Equity

$164,468 (58%)

Primary Contact
$285K Est. Value

123 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,840 sq ft
2,200 sq ft lot
Last Sale Date

8/31/2018

Est Equity

$133,160 (47%)

Primary Contact
$288K Est. Value

125 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,876 sq ft
2,200 sq ft lot
Last Sale Date

1/10/2018

Est Equity

$169,765 (59%)

Primary Contact
$297K Est. Value

127 Acorn Dr, Chestertown, MD 21620

3 beds
2 baths
Built: 2005
1,864 sq ft
4,070 sq ft lot
Last Sale Date

4/26/2012

Est Equity

$303,873 (102%)

Primary Contact
$540K Est. Value

100 Adela Way, Chestertown, MD 21620

4 beds
3 baths
Built: 2008
2,492 sq ft
13,739 sq ft lot
Last Sale Date

12/20/2018

Est Equity

$208,175 (39%)

Primary Contact
$488K Est. Value

101 Adela Way, Chestertown, MD 21620

4 beds
3 baths
Built: 2006
3,534 sq ft
11,047 sq ft lot
Last Sale Date

9/3/2021

Est Equity

$142,811 (29%)

Primary Contact
$501K Est. Value

102 Adela Way, Chestertown, MD 21620

5 beds
2 baths
Built: 2008
3,484 sq ft
17,621 sq ft lot
Last Sale Date

3/30/2012

Est Equity

$262,912 (53%)

Primary Contact
$455K Est. Value

103 Adela Way, Chestertown, MD 21620

3 beds
2 baths
Built: 2008
3,676 sq ft
10,295 sq ft lot
Last Sale Date

3/13/2025

Est Equity

$412,128 (91%)

Primary Contact
$412K Est. Value

105 Adela Way, Chestertown, MD 21620

2 baths
Built: 2006
2,748 sq ft
10,749 sq ft lot
Last Sale Date

1/19/2007

Est Equity

$426,518 (104%)

Primary Contact
$468K Est. Value

107 Adela Way, Chestertown, MD 21620

4 beds
2 baths
Built: 2010
2,606 sq ft
10,643 sq ft lot
Last Sale Date

9/15/2023

Est Equity

$36,921 (8%)

Primary Contact
$493K Est. Value

109 Adela Way, Chestertown, MD 21620

4 beds
3 baths
Built: 2007
2,997 sq ft
11,787 sq ft lot
Last Sale Date

4/17/2020

Est Equity

$144,817 (29%)

Primary Contact
$442K Est. Value

111 Adela Way, Chestertown, MD 21620

3 baths
Built: 2007
2,390 sq ft
11,477 sq ft lot
Last Sale Date

11/15/2007

Est Equity

$184,269 (42%)

Primary Contact
$423K Est. Value

113 Adela Way, Chestertown, MD 21620

5 beds
2 baths
Built: 2006
2,492 sq ft
13,608 sq ft lot
Last Sale Date

3/31/2015

Est Equity

$253,797 (60%)

Primary Contact
$456K Est. Value

115 Adela Way, Chestertown, MD 21620

2 baths
Built: 2006
2,654 sq ft
14,557 sq ft lot
Last Sale Date

1/18/2007

Est Equity

$292,208 (64%)

Primary Contact
$394K Est. Value

117 Adela Way, Chestertown, MD 21620

4 beds
2 baths
Built: 2007
1,944 sq ft
13,209 sq ft lot
Last Sale Date

3/6/2014

Est Equity

$236,385 (60%)

Primary Contact
12389

FAQs about Chestertown, MD

A free property search in Chestertown on Rew Online can help you explore detailed residence insights across the city. You can analyze property and ownership information to evaluate acquisition opportunities and real estate investment potential.

It’s known that in the city, the median estimated equity balance is $266,708, reflecting the typical financial position of property owners and serving as an indicator of equity strength across Chestertown.

According to public records, 544 houses in the city feature a pool, making it easier for potential home buyers to determine properties with private swimming amenities.

The land value, which typically reflects location, size of the lot, development potential, and infrastructure access, among other things, is around $90,800 in the city.

A property in Chestertown is usually considered more desirable when it includes proximity to major employment hubs, schools, hospitals, and other amenities, as well as access to transportation and neighborhood appeal. Houses in up-and-coming neighborhoods tend to also experience housing demand and increasing interest from homebuyers and investors.

An up-and-coming neighborhood in Chestertown is defined by a combination of factors such as rising property values, increasing demand, and visible signs of development. In addition, developing neighborhoods may attract investors and new residents due to affordable housing compared to nearby markets.