Chester Virginia Homes for Sale

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12020 Winfree Street Chester, VA MLS# 2604831 - Image 1

12020 Winfree Street Chester, VA MLS# 2604831 - Image 2

12020 Winfree Street Chester, VA MLS# 2604831 - Image 3

12020 Winfree Street Chester, VA MLS# 2604831 - Image 4

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12020 Winfree Street Chester, VA MLS# 2604831 - Image 15

12020 Winfree Street Chester, VA MLS# 2604831 - Image 16

1 of 16

$640,000

0.0

Baths

2,716

Sq.Ft.

12020 Winfree Street

Chester, VA

12601 Inverness Drive Chester, VA MLS# 2624463 - Image 2

12601 Inverness Drive Chester, VA MLS# 2624463 - Image 3

12601 Inverness Drive Chester, VA MLS# 2624463 - Image 4

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Virtual Tour

1 of 51

$640,000

Beds

3.1

Baths

4,037

Sq.Ft.

12601 Inverness Drive

Chester, VA

14500 Happy Hill Chester, VA MLS# 2627064 - Image 2

14500 Happy Hill Chester, VA MLS# 2627064 - Image 3

14500 Happy Hill Chester, VA MLS# 2627064 - Image 4

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Recently Listed with Virtual Tour

1 of 58

$627,500

Beds

2.1

Baths

3,598

Sq.Ft.

14500 Happy Hill

Chester, VA

THE TIME TO SELL IS NOW!

12603 Hogans Drive Chester, VA MLS# 2627275 - Image 1

12603 Hogans Drive Chester, VA MLS# 2627275 - Image 2

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1 of 99

$625,000

Beds

3.0

Baths

3,733

Sq.Ft.

12603 Hogans Drive

Chester, VA

2018 James Overlook Drive Chester, VA MLS# 2620941 - Image 2

2018 James Overlook Drive Chester, VA MLS# 2620941 - Image 3

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2018 James Overlook Drive Chester, VA MLS# 2620941 - Image 54

1 of 54

$619,990

Beds

4.0

Baths

3,667

Sq.Ft.

2018 James Overlook Drive

Chester, VA

1719 Almer Court Chester, VA MLS# 2627040 - Image 2

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Recently Listed

1 of 51

$619,900

Beds

3.0

Baths

3,082

Sq.Ft.

1719 Almer Court

Chester, VA

4512 Forrestal Road Chester, VA MLS# 2623075 - Image 2

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Virtual Tour

1 of 60

$615,000

Beds

4.1

Baths

4,217

Sq.Ft.

4512 Forrestal Road

Chester, VA

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4013 Cresthill Road Chester, VA MLS# 2626331 - Image 47

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4013 Cresthill Road Chester, VA MLS# 2626331 - Image 56

4013 Cresthill Road Chester, VA MLS# 2626331 - Image 57

4013 Cresthill Road Chester, VA MLS# 2626331 - Image 58

4013 Cresthill Road Chester, VA MLS# 2626331 - Image 59

4013 Cresthill Road Chester, VA MLS# 2626331 - Image 60

1 of 60

OPEN HOUSE: Sunday 10/18 2:00 PM - 4:00 PM

$599,000

Beds

2.1

Baths

3,000

Sq.Ft.

4013 Cresthill Road

Chester, VA

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 2

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 3

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 4

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11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 54

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 55

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 56

11536 Chester Village Drive Chester, VA MLS# 2621368 - Image 57

1 of 57

$589,000

Beds

3.1

Baths

3,158

Sq.Ft.

11536 Chester Village Drive

Chester, VA

554 Greymont Lane Chester, VA MLS# 2625274 - Image 2

554 Greymont Lane Chester, VA MLS# 2625274 - Image 3

554 Greymont Lane Chester, VA MLS# 2625274 - Image 4

554 Greymont Lane Chester, VA MLS# 2625274 - Image 5

554 Greymont Lane Chester, VA MLS# 2625274 - Image 6

554 Greymont Lane Chester, VA MLS# 2625274 - Image 7

554 Greymont Lane Chester, VA MLS# 2625274 - Image 8

554 Greymont Lane Chester, VA MLS# 2625274 - Image 9

554 Greymont Lane Chester, VA MLS# 2625274 - Image 10

554 Greymont Lane Chester, VA MLS# 2625274 - Image 11

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554 Greymont Lane Chester, VA MLS# 2625274 - Image 13

554 Greymont Lane Chester, VA MLS# 2625274 - Image 14

554 Greymont Lane Chester, VA MLS# 2625274 - Image 15

554 Greymont Lane Chester, VA MLS# 2625274 - Image 16

554 Greymont Lane Chester, VA MLS# 2625274 - Image 17

554 Greymont Lane Chester, VA MLS# 2625274 - Image 18

554 Greymont Lane Chester, VA MLS# 2625274 - Image 19

554 Greymont Lane Chester, VA MLS# 2625274 - Image 20

554 Greymont Lane Chester, VA MLS# 2625274 - Image 21

554 Greymont Lane Chester, VA MLS# 2625274 - Image 22

554 Greymont Lane Chester, VA MLS# 2625274 - Image 23

554 Greymont Lane Chester, VA MLS# 2625274 - Image 24

554 Greymont Lane Chester, VA MLS# 2625274 - Image 25

554 Greymont Lane Chester, VA MLS# 2625274 - Image 26

554 Greymont Lane Chester, VA MLS# 2625274 - Image 27

554 Greymont Lane Chester, VA MLS# 2625274 - Image 28

554 Greymont Lane Chester, VA MLS# 2625274 - Image 29

554 Greymont Lane Chester, VA MLS# 2625274 - Image 30

554 Greymont Lane Chester, VA MLS# 2625274 - Image 31

554 Greymont Lane Chester, VA MLS# 2625274 - Image 32

Virtual Tour

1 of 32

$549,950

Beds

2.1

Baths

2,948

Sq.Ft.

554 Greymont Lane

Chester, VA

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 2

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 3

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 4

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 5

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4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 7

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4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 38

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 39

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 40

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 41

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 42

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 43

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 44

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 45

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 46

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 47

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4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 49

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4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 54

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 55

4248 Poplar Village Drive Chester, VA MLS# 2627750 - Image 56

Recently Listed

1 of 56

$549,950

Beds

3.1

Baths

2,963

Sq.Ft.

4248 Poplar Village Drive

Chester, VA

1799 Outrigger Drive Chester, VA MLS# 2624849 - Image 2

1799 Outrigger Drive Chester, VA MLS# 2624849 - Image 3

1799 Outrigger Drive Chester, VA MLS# 2624849 - Image 4

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1799 Outrigger Drive Chester, VA MLS# 2624849 - Image 38

1799 Outrigger Drive Chester, VA MLS# 2624849 - Image 39

Virtual Tour

1 of 39

$545,000

Beds

3.0

Baths

2,164

Sq.Ft.

1799 Outrigger Drive

Chester, VA

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 2

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 3

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 4

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 5

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 6

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1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 11

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1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 13

1961 Enon Station Drive Chester, VA MLS# 2624384 - Image 14

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1 of 51

$535,000

Beds

3.0

Baths

2,719

Sq.Ft.

1961 Enon Station Drive

Chester, VA

1900 Galley Place Chester, VA MLS# 2606849 - Image 2

1900 Galley Place Chester, VA MLS# 2606849 - Image 3

1900 Galley Place Chester, VA MLS# 2606849 - Image 4

1900 Galley Place Chester, VA MLS# 2606849 - Image 5

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1900 Galley Place Chester, VA MLS# 2606849 - Image 7

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1900 Galley Place Chester, VA MLS# 2606849 - Image 39

1900 Galley Place Chester, VA MLS# 2606849 - Image 40

New Construction

1 of 40

$525,000

Beds

3.0

Baths

2,620

Sq.Ft.

1900 Galley Place

Chester, VA

14107 Beachmere Road Chester, VA MLS# 2624097 - Image 2

14107 Beachmere Road Chester, VA MLS# 2624097 - Image 3

14107 Beachmere Road Chester, VA MLS# 2624097 - Image 4

14107 Beachmere Road Chester, VA MLS# 2624097 - Image 5

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14107 Beachmere Road Chester, VA MLS# 2624097 - Image 33

1 of 33

$525,000

Beds

2.1

Baths

2,847

Sq.Ft.

14107 Beachmere Road

Chester, VA

12600 Brook Lane Chester, VA MLS# 2624518 - Image 2

12600 Brook Lane Chester, VA MLS# 2624518 - Image 3

12600 Brook Lane Chester, VA MLS# 2624518 - Image 4

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12600 Brook Lane Chester, VA MLS# 2624518 - Image 42

12600 Brook Lane Chester, VA MLS# 2624518 - Image 43

Virtual Tour

1 of 43

$525,000

Beds

2.1

Baths

3,285

Sq.Ft.

12600 Brook Lane

Chester, VA

5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 2

5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 3

5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 4

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5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 40

5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 41

5305 Ecoff Avenue Chester, VA MLS# 2625743 - Image 42

Virtual Tour

1 of 42

$525,000

Beds

3.1

Baths

1,996

Sq.Ft.

5305 Ecoff Avenue

Chester, VA

5640 Teterling Court Chester, VA MLS# 2625819 - Image 2

5640 Teterling Court Chester, VA MLS# 2625819 - Image 3

5640 Teterling Court Chester, VA MLS# 2625819 - Image 4

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1 of 47

$525,000

Beds

3.0

Baths

3,559

Sq.Ft.

5640 Teterling Court

Chester, VA

14460 Woodleigh Drive Chester, VA MLS# 2626934 - Image 2

14460 Woodleigh Drive Chester, VA MLS# 2626934 - Image 3

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1 of 43

$525,000

Beds

3.0

Baths

3,498

Sq.Ft.

14460 Woodleigh Drive

Chester, VA

Address not provided Chester, VA MLS# 2502282 - Image 2

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New Construction

1 of 41

$521,900

Beds

2.0

Baths

2,393

Sq.Ft.

Address not provided

Chester, VA

About Chester

Listings in Chester, VA: 214
Estimated median home price: $415,000

Chester VA Homes for Sale & Properties

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

Homes for Sale by Price in Chester, VA

Price	Count
$0 - 100K	10
$100K - 200K	5
$200K - 300K	12
$300K - 400K	76
$400K - 500K	60
$500K - 600K	24
$600K - 700K	12
$700K - 800K	1
$800K - 900K	3
$900K - 1M	2
$1M - Max	9

Homes for Sale by Type in Chester, VA

Property Type	Count
Single Family	174
Townhouse	14
Condo	5
Commercial	4
Rental	8
Lots and Land	16
Condo/Town/CoOp	0
CoOp	0
Multi Family	1
Mobile Home	0
Farms	0

(Data as of 10/18/2026)

Information deemed reliable but not guaranteed.

Properties marked with the CVRMLS icon are provided courtesy of Central Virginia Regional Multiple Listing Service, LLC and detailed information about them includes the name of the listing brokers.

The multiple listing information is provided by Central Virginia Regional Multiple Listing Service, LLC from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 10/18/2026.

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