View 102 Boatswain Way # 2921 Chester, MD MLS# MDQA2016674
$889,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

102 Boatswain Way # 2921

Chester, MD

Bright
Courtesy of KOVO REALTY
View 501 Teal Court Chester, MD MLS# MDQA2016642
$310,000
5

Beds

3.1

Baths

1,073

Sq.Ft.

501 Teal Court

Chester, MD

Bright
Courtesy of SAMSON PROPERTIES
View 249 Warbler Way Chester, MD MLS# MDQA2016488
  • Adult Community
1 of 68
$679,000
2

Beds

2.0

Baths

2,025

Sq.Ft.

249 Warbler Way

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
The time to sell is now! THE TIME TO SELL IS NOW!
View 23 Queen Victoria Way Chester, MD MLS# MDQA2016422
$445,000
2

Beds

2.0

Baths

1,104

Sq.Ft.

23 Queen Victoria Way

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 34 Queen Anne Way # F Chester, MD MLS# MDQA2016474
$349,900
1

Beds

1.0

Baths

724

Sq.Ft.

34 Queen Anne Way # F

Chester, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 1872 Harbor Drive Chester, MD MLS# MDQA2016514
$485,000
3

Beds

2.0

Baths

1,486

Sq.Ft.

1872 Harbor Drive

Chester, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 719 Warbler Way Chester, MD MLS# MDQA2016506
  • Adult Community
1 of 38
$889,990
4

Beds

3.0

Baths

2,791

Sq.Ft.

719 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1838 Sherman Drive Chester, MD MLS# MDQA2016438
$387,500
3

Beds

2.0

Baths

1,204

Sq.Ft.

1838 Sherman Drive

Chester, MD

Bright
Courtesy of KELLER WILLIAMS REALTY CENTRE
View 2000 Herons Nest Way # 401 Chester, MD MLS# MDQA2016336
  • Adult Community with Virtual Tour
1 of 113
$750,000
3

Beds

2.1

Baths

2,602

Sq.Ft.

2000 Herons Nest Way # 401

Chester, MD

Bright
Courtesy of REAL BROKER, LLC
View 34 Queen Anne Way Chester, MD MLS# MDQA2016464
  • Virtual Tour
1 of 52
$549,000
2

Beds

2.1

Baths

1,586

Sq.Ft.

34 Queen Anne Way

Chester, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 8 Queen Victoria Way Chester, MD MLS# MDQA2016442
$249,000
1

Beds

1.0

Baths

724

Sq.Ft.

8 Queen Victoria Way

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 539 Warbler Way Chester, MD MLS# MDQA2016406
  • Adult Community
1 of 59
$789,990
3

Beds

3.0

Baths

2,789

Sq.Ft.

539 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1905 Bayside Drive Chester, MD MLS# MDQA2016340
$299,900
2

Beds

1.1

Baths

1,220

Sq.Ft.

1905 Bayside Drive

Chester, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358
$799,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360
$799,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3043

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2016230
  • Adult Community
1 of 32
OPEN HOUSE: Saturday 4/25 11:00 AM - 1:00 PM
$494,900
2

Beds

2.1

Baths

2,003

Sq.Ft.

1000 Herons Nest Way # 23

Chester, MD

Bright
Courtesy of EXP REALTY, LLC
View 1150 Little Creek Road Chester, MD MLS# MDQA2016206
$375,000
3

Beds

1.1

Baths

2,200

Sq.Ft.

1150 Little Creek Road

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 27 Queen Mary Court # F Chester, MD MLS# MDQA2016200
$419,000
2

Beds

2.0

Baths

1,380

Sq.Ft.

27 Queen Mary Court # F

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 1868 Roberta Drive Chester, MD MLS# MDQA2016194
$749,500
5

Beds

3.1

Baths

3,250

Sq.Ft.

1868 Roberta Drive

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 230 Switchgrass Way # 21 Chester, MD MLS# MDQA2016166
  • Adult Community with Virtual Tour
1 of 106
$675,000
3

Beds

2.1

Baths

2,602

Sq.Ft.

230 Switchgrass Way # 21

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.

About Chester

Listings in Chester, MD

108

Estimated median home price

$649,990
Chester MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chester, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, MD.

Homes for Sale by Price in Chester, MD

PriceCount
$0 - 100K2
$100K - 200K1
$200K - 300K8
$300K - 400K10
$400K - 500K13
$500K - 600K16
$600K - 700K13
$700K - 800K17
$800K - 900K7
$900K - 1M10
$1M - Max11

Homes for Sale by Type in Chester, MD

Property TypeCount
Single Family46
Townhouse0
Condo58
Commercial0
Rental15
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/19/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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 sold or are no longer being offered for sale.

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