View 1414 Kings Highway Chester, NY MLS# 965992
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1 of 9
$879,900
4

Beds

2.1

Baths

3,200

Sq.Ft.

1414 Kings Highway

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 2 Pine Hill Road Chester, NY MLS# 974429
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1 of 36
$875,000
3

Beds

2.1

Baths

2,302

Sq.Ft.

2 Pine Hill Road

Chester, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY
View 10 Wells Sweep Lane Chester, NY MLS# 966048
Save 10 Wells Sweep Lane Chester, NY MLS# 966048
1 of 8
$869,900
4

Beds

2.1

Baths

3,000

Sq.Ft.

10 Wells Sweep Lane

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 5 Gabriels Drive Chester, NY MLS# 983687
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1 of 45
$850,000
4

Beds

2.1

Baths

2,722

Sq.Ft.

5 Gabriels Drive

Chester, NY

Courtesy of Q HOME SALES
View 32 Mountainside Drive Chester, NY MLS# 901144
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1 of 8
$849,900
4

Beds

2.1

Baths

2,603

Sq.Ft.

32 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View 4 Debbie Court Chester, NY MLS# 962813
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$840,000
5

Beds

5.1

Baths

5,403

Sq.Ft.

4 Debbie Court

Chester, NY

Courtesy of FLAG REALTY GROUP
View 148 Brookside Avenue Chester, NY MLS# H6146719
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1 of 3
$799,000

148 Brookside Avenue

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 558 Pine Hill Road Chester, NY MLS# 958731
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1 of 50
$799,000
4

Beds

2.1

Baths

3,120

Sq.Ft.

558 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 1071 Craigville Road Chester, NY MLS# 976307
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1 of 48
$795,000
4

Beds

2.1

Baths

2,780

Sq.Ft.

1071 Craigville Road

Chester, NY

Courtesy of MS REALTY GROUP USA, INC
View 90 Pewter Circle Chester, NY MLS# 981270
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1 of 5
$759,900
4

Beds

2.1

Baths

2,250

Sq.Ft.

90 Pewter Circle

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 16 Oxford Springs Road Chester, NY MLS# 935115
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1 of 43
$750,000
3

Beds

3.0

Baths

2,870

Sq.Ft.

16 Oxford Springs Road

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 17 Woodridge Drive Chester, NY MLS# 972648
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1 of 50
$749,000
4

Beds

2.1

Baths

2,524

Sq.Ft.

17 Woodridge Drive

Chester, NY

Courtesy of EXP REALTY
View 55 Beverly Road Chester, NY MLS# 977281
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1 of 49
$735,000
4

Beds

3.1

Baths

3,356

Sq.Ft.

55 Beverly Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 7 Park Place Chester, NY MLS# 927218
Save 7 Park Place Chester, NY MLS# 927218
1 of 48
$730,000
4

Beds

3.1

Baths

2,780

Sq.Ft.

7 Park Place

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 9 Country Woods Drive Chester, NY MLS# 925049
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1 of 30
$725,000
5

Beds

2.1

Baths

3,124

Sq.Ft.

9 Country Woods Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 487 Black Meadow Road Chester, NY MLS# 960665
Save 487 Black Meadow Road Chester, NY MLS# 960665
1 of 50
$725,000
6

Beds

3.1

Baths

4,204

Sq.Ft.

487 Black Meadow Road

Chester, NY

Courtesy of JOSEPH BARATTA COMPANY REALTY
View 78 Goshen Road Chester, NY MLS# 968517
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1 of 50
$725,000
4

Beds

2.2

Baths

3,908

Sq.Ft.

78 Goshen Road

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 5 Bens Way Chester, NY MLS# 959390
Save 5 Bens Way Chester, NY MLS# 959390
1 of 26
$699,999
4

Beds

2.1

Baths

2,544

Sq.Ft.

5 Bens Way

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 34 Mountainside Drive Chester, NY MLS# 956879
Save 34 Mountainside Drive Chester, NY MLS# 956879
1 of 8
$699,990
4

Beds

3.0

Baths

1,867

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View 360 Prospect Road Chester, NY MLS# 944607
Save 360 Prospect Road Chester, NY MLS# 944607
1 of 50
$699,000
3

Beds

3.0

Baths

3,000

Sq.Ft.

360 Prospect Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC

About Chester

Listings in Chester, NY

69

Estimated median home price

$699,000
Chester NY Homes for Sale & Properties

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

Homes for Sale by Price in Chester, NY

Price Count
$0 - 100K 0
$100K - 200K 3
$200K - 300K 8
$300K - 400K 11
$400K - 500K 7
$500K - 600K 2
$600K - 700K 7
$700K - 800K 11
$800K - 900K 6
$900K - 1M 4
$1M - Max 10

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 42
Townhouse 0
Condo 10
Commercial 5
Rental 26
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 4/20/2026)

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Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

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