Chester, MD Real Estate Listings

55 real estate listings match this search criteria near Chester.

Active
26 photos
$969,990
2 bd, 2.5 ba, 2,010 Sq Ft
118 Kinglet CourtChester, MD 21619#MDQA2018806
Single Family Residence
Active
25 photos
$999,990
3 bd, 3 ba, 2,772 Sq Ft
114 Kinglet CourtChester, MD 21619#MDQA2018804
Single Family Residence
Active
38 photos
$299,900
3 bd, 2.5 ba, 1,440 Sq Ft
54 Queen Caroline Court DChester, MD 21619#MDQA2017146
Condominium
Active
31 photos
$410,000
3 bd, 2.5 ba, 1,899 Sq Ft
510 Auckland Way Unit 143Chester, MD 21619#MDQA2018734
Condominium
Active
36 photos
$599,900
3 bd, 3.5 ba, 2,076 Sq Ft
1012 Auckland WayChester, MD 21619#MDQA2018742
Condominium
Active
56 photos
$998,000
3 bd, 2.5 ba, 2,602 Sq Ft
111 Marshgrass Way 41Chester, MD 21619#MDQA2017940
Condominium
Active
46 photos
$349,900
3 bd, 2.5 ba, 1,440 Sq Ft
54F Queen Caroline Court Unit FChester, MD 21619#MDQA2017082
Condominium
Active
48 photos
$425,500
3 bd, 3.5 ba, 2,100 Sq Ft
807 Auckland WayChester, MD 21619#MDQA2017442
Condominium
Active
50 photos
$429,900
3 bd, 2.5 ba, 1,595 Sq Ft
106 Bodys Neck RoadChester, MD 21619#MDQA2017432
Condominium
Active
14 photos
$539,000
2 bd, 2.5 ba, 1,680 Sq Ft
15 Queen Anne Way E EChester, MD 21619#MDQA2018746
Condominium
Active
39 photos
$499,000
2 bd, 2.5 ba, 1,680 Sq Ft
7 Queen Victoria Way B BChester, MD 21619#MDQA2018794
Condominium
Active
63 photos
$749,000
4 bd, 3.5 ba, 2,185 Sq Ft
134 Richard Ingle WayChester, MD 21619#MDQA2017930
Single Family Residence
Active
70 photos
$492,500
2 bd, 2.5 ba, 1,900 Sq Ft
4000 Herons Nest Way 22Chester, MD 21619#MDQA2015800
Condominium
Active
35 photos
$825,000
4 bd, 3.5 ba, 3,312 Sq Ft
232 Evelyne StreetChester, MD 21619#MDQA2017378
Single Family Residence
Active
65 photos
$599,900
3 bd, 2 ba, 1,688 Sq Ft
315 Bentons Pleasure RoadChester, MD 21619#MDQA2017854
Single Family Residence
Active
56 photos
$485,000
2 bd, 2.5 ba, 1,900 Sq Ft
1000 Herons Nest Way 22Chester, MD 21619#MDQA2016820
Condominium
Active
13 photos
$6,000,000
12,036 Sq Ft
1406 Main StreetStevensville, MD 21666#MDQA2017804
Retail
Active
46 photos
$315,000
3 bd, 2.5 ba, 1,302 Sq Ft
5011 Bridgepointe DriveChester, MD 21619#MDQA2017274
Condominium
Active
57 photos
$665,000
2 bd, 2.5 ba, 1,993 Sq Ft
228 Bayberry DriveChester, MD 21619#MDQA2018728
Single Family Residence
Active
52 photos
$815,000
4 bd, 2.5 ba, 2,870 Sq Ft
231 Evelyne StreetChester, MD 21619#MDQA2018740
Single Family Residence
Active
38 photos
$329,000
2 bd, 2.5 ba, 1,440 Sq Ft
53 Queen Caroline Court EChester, MD 21619#MDQA2018730
Townhouse
Active
51 photos
$375,000
3 bd, 3 ba, 1,899 Sq Ft
512 Auckland WayChester, MD 21619#MDQA2018750
Condominium
Active
40 photos
$318,500
2 bd, 2.5 ba, 1,312 Sq Ft
45 Queen Neva Court GChester, MD 21619#MDQA2017164
Condominium
Active
37 photos
$369,900
3 bd, 2.5 ba, 1,899 Sq Ft
108 Blenny LaneChester, MD 21619#MDQA2018242
Condominium

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 in which EXIT Realty participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and 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 this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright ©2026 Bright MLS. All rights reserved.

55 real estate listings match this search criteria near Chester.

Active
26 photos
$969,990
2 bd, 2.5 ba, 2,010 Sq Ft
118 Kinglet CourtChester, MD 21619#MDQA2018806
Single Family Residence
Active
25 photos
$999,990
3 bd, 3 ba, 2,772 Sq Ft
114 Kinglet CourtChester, MD 21619#MDQA2018804
Single Family Residence
Active
38 photos
$299,900
3 bd, 2.5 ba, 1,440 Sq Ft
54 Queen Caroline Court DChester, MD 21619#MDQA2017146
Condominium
Active
31 photos
$410,000
3 bd, 2.5 ba, 1,899 Sq Ft
510 Auckland Way Unit 143Chester, MD 21619#MDQA2018734
Condominium
Active
36 photos
$599,900
3 bd, 3.5 ba, 2,076 Sq Ft
1012 Auckland WayChester, MD 21619#MDQA2018742
Condominium
Active
56 photos
$998,000
3 bd, 2.5 ba, 2,602 Sq Ft
111 Marshgrass Way 41Chester, MD 21619#MDQA2017940
Condominium
Active
46 photos
$349,900
3 bd, 2.5 ba, 1,440 Sq Ft
54F Queen Caroline Court Unit FChester, MD 21619#MDQA2017082
Condominium
Active
48 photos
$425,500
3 bd, 3.5 ba, 2,100 Sq Ft
807 Auckland WayChester, MD 21619#MDQA2017442
Condominium
Active
50 photos
$429,900
3 bd, 2.5 ba, 1,595 Sq Ft
106 Bodys Neck RoadChester, MD 21619#MDQA2017432
Condominium
Active
14 photos
$539,000
2 bd, 2.5 ba, 1,680 Sq Ft
15 Queen Anne Way E EChester, MD 21619#MDQA2018746
Condominium
Active
39 photos
$499,000
2 bd, 2.5 ba, 1,680 Sq Ft
7 Queen Victoria Way B BChester, MD 21619#MDQA2018794
Condominium
Active
63 photos
$749,000
4 bd, 3.5 ba, 2,185 Sq Ft
134 Richard Ingle WayChester, MD 21619#MDQA2017930
Single Family Residence
Active
70 photos
$492,500
2 bd, 2.5 ba, 1,900 Sq Ft
4000 Herons Nest Way 22Chester, MD 21619#MDQA2015800
Condominium
Active
35 photos
$825,000
4 bd, 3.5 ba, 3,312 Sq Ft
232 Evelyne StreetChester, MD 21619#MDQA2017378
Single Family Residence
Active
65 photos
$599,900
3 bd, 2 ba, 1,688 Sq Ft
315 Bentons Pleasure RoadChester, MD 21619#MDQA2017854
Single Family Residence
Active
56 photos
$485,000
2 bd, 2.5 ba, 1,900 Sq Ft
1000 Herons Nest Way 22Chester, MD 21619#MDQA2016820
Condominium
Active
13 photos
$6,000,000
12,036 Sq Ft
1406 Main StreetStevensville, MD 21666#MDQA2017804
Retail
Active
46 photos
$315,000
3 bd, 2.5 ba, 1,302 Sq Ft
5011 Bridgepointe DriveChester, MD 21619#MDQA2017274
Condominium
Active
57 photos
$665,000
2 bd, 2.5 ba, 1,993 Sq Ft
228 Bayberry DriveChester, MD 21619#MDQA2018728
Single Family Residence
Active
52 photos
$815,000
4 bd, 2.5 ba, 2,870 Sq Ft
231 Evelyne StreetChester, MD 21619#MDQA2018740
Single Family Residence
Active
38 photos
$329,000
2 bd, 2.5 ba, 1,440 Sq Ft
53 Queen Caroline Court EChester, MD 21619#MDQA2018730
Townhouse
Active
51 photos
$375,000
3 bd, 3 ba, 1,899 Sq Ft
512 Auckland WayChester, MD 21619#MDQA2018750
Condominium
Active
40 photos
$318,500
2 bd, 2.5 ba, 1,312 Sq Ft
45 Queen Neva Court GChester, MD 21619#MDQA2017164
Condominium
Active
37 photos
$369,900
3 bd, 2.5 ba, 1,899 Sq Ft
108 Blenny LaneChester, MD 21619#MDQA2018242
Condominium

Market Overview — Chester, MD

Showing Chester, MD

Property type

ResidentialCommercial

Transaction

For SaleFor Lease

Area Average

Median over the active for-sale listings

$645,000
Median Listing Price: 49
Median Days on EXIT Realty: 2,003
Median Sq Ft: $293
Median Price per Sq Ft

Compare

Compare Chester, MD to another area

Median price, days on market and size comparison by area
Area	Median Listing Price	Median Days on EXIT Realty	Median Sq Ft	Median Price per Sq Ft	Actions
Chester, MD	$645,000	49	2,003	$293

Market Composition

What's on the market

78%Residential90 active
12%For Lease14 active
5%Commercial Lease6 active
3%Land3 active
<1%Commercial1 active
<1%Multi-Family1 active

Active listings by price

Under $200K2% · 2
$200K-$400K14% · 13
$400K-$600K32% · 29
$600K-$800K23% · 21
$800K-$1M21% · 19
Over $1M8% · 7

Median Price Trend

Jun 2026: $379,000 -15.8%Oct 2026: $319,000

Thinking of selling?

EXIT Realty’s Chester agents know these numbers street by street — and bring the insight and negotiating experience to turn them into your sale price.

Sell a home in Chester

Nearby Schools

Elementary 8

Kent Island Elementary School
Stevensville, MD · 1.0 mi away
Bayside Elementary School
Stevensville, MD · 1.0 mi away
Matapeake Elementary School
Stevensville, MD · 2.6 mi away
Grasonville Elementary School
Grasonville, MD · 5.5 mi away
Cape St Claire Elementary School
Annapolis, MD · 9.4 mi away
Naval Academy Primary School
Annapolis, MD · 9.5 mi away
Windsor Farm Elementary School
Annapolis, MD · 10.0 mi away
Windsor Farm Elementary School
Annapolis, MD · 10.0 mi away

Secondary 2

Kent Island High School
Stevensville, MD · 1.5 mi away
Broadneck High School
Annapolis, MD · 9.8 mi away

Other schools 10

Kent Island Christian School
Chester, MD · 0.1 mi away
Lighthouse Christian Academy
Stevensville, MD · 1.8 mi away
The Kinder Garden
Stevensville, MD · 2.1 mi away
Christ Episcopal Church Day School
Stevensville, MD · 2.9 mi away
Queen Anne's County
Grasonville, MD · 5.5 mi away
New Covenant Christian Academy
Queenstown, MD · 7.4 mi away
In Faith Christian School
Annapolis, MD · 9.4 mi away
St. Margaret's Episcopal Church
Annapolis, MD · 9.8 mi away
Harbour School
Annapolis, MD · 9.9 mi away
Wesley Brown Fieldhouse
Annapolis, MD · 10.2 mi away

Chester, MD Real Estate Listings

Chester, MD Real Estate Listings

118 Kinglet CourtChester, MD 21619#MDQA2018806

114 Kinglet CourtChester, MD 21619#MDQA2018804

54 Queen Caroline Court DChester, MD 21619#MDQA2017146

510 Auckland Way Unit 143Chester, MD 21619#MDQA2018734

1012 Auckland WayChester, MD 21619#MDQA2018742

111 Marshgrass Way 41Chester, MD 21619#MDQA2017940

54F Queen Caroline Court Unit FChester, MD 21619#MDQA2017082

807 Auckland WayChester, MD 21619#MDQA2017442

106 Bodys Neck RoadChester, MD 21619#MDQA2017432

15 Queen Anne Way E EChester, MD 21619#MDQA2018746

7 Queen Victoria Way B BChester, MD 21619#MDQA2018794

134 Richard Ingle WayChester, MD 21619#MDQA2017930

4000 Herons Nest Way 22Chester, MD 21619#MDQA2015800

232 Evelyne StreetChester, MD 21619#MDQA2017378

315 Bentons Pleasure RoadChester, MD 21619#MDQA2017854

1000 Herons Nest Way 22Chester, MD 21619#MDQA2016820

1406 Main StreetStevensville, MD 21666#MDQA2017804

5011 Bridgepointe DriveChester, MD 21619#MDQA2017274

228 Bayberry DriveChester, MD 21619#MDQA2018728

231 Evelyne StreetChester, MD 21619#MDQA2018740

53 Queen Caroline Court EChester, MD 21619#MDQA2018730

512 Auckland WayChester, MD 21619#MDQA2018750

45 Queen Neva Court GChester, MD 21619#MDQA2017164

108 Blenny LaneChester, MD 21619#MDQA2018242

118 Kinglet CourtChester, MD 21619#MDQA2018806

114 Kinglet CourtChester, MD 21619#MDQA2018804

54 Queen Caroline Court DChester, MD 21619#MDQA2017146

510 Auckland Way Unit 143Chester, MD 21619#MDQA2018734

1012 Auckland WayChester, MD 21619#MDQA2018742

111 Marshgrass Way 41Chester, MD 21619#MDQA2017940

54F Queen Caroline Court Unit FChester, MD 21619#MDQA2017082

807 Auckland WayChester, MD 21619#MDQA2017442

106 Bodys Neck RoadChester, MD 21619#MDQA2017432

15 Queen Anne Way E EChester, MD 21619#MDQA2018746

7 Queen Victoria Way B BChester, MD 21619#MDQA2018794

134 Richard Ingle WayChester, MD 21619#MDQA2017930

4000 Herons Nest Way 22Chester, MD 21619#MDQA2015800

232 Evelyne StreetChester, MD 21619#MDQA2017378

315 Bentons Pleasure RoadChester, MD 21619#MDQA2017854

1000 Herons Nest Way 22Chester, MD 21619#MDQA2016820

1406 Main StreetStevensville, MD 21666#MDQA2017804

5011 Bridgepointe DriveChester, MD 21619#MDQA2017274

228 Bayberry DriveChester, MD 21619#MDQA2018728

231 Evelyne StreetChester, MD 21619#MDQA2018740

53 Queen Caroline Court EChester, MD 21619#MDQA2018730

512 Auckland WayChester, MD 21619#MDQA2018750

45 Queen Neva Court GChester, MD 21619#MDQA2017164

108 Blenny LaneChester, MD 21619#MDQA2018242

Market Overview — Chester, MD

Area Average

Compare

Market Composition

What's on the market

Active listings by price

Median Price Trend

Nearby Schools

Elementary 8

Secondary 2

Other schools 10