2 Bedroom Homes in Chester, NY

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3 beds New construction With a pool

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4 Listings

2 Bedroom Homes in Chester, NY

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4 Listings

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2 Bedroom Homes in Chester, NY

4 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

18Active
$299,000
2 bd · 1 ba · 1,084 sqft
2124 Whispering Hills, Chester, NY
Beverly Huaman · Howard Hanna Rand Realty
28Active
$290,000
2 bd · 2 ba · 1,053 sqft
1005 Whispering Hills, Chester, NY
Kristie A. Jacques · Century 21 Full Service Realty
Price Reduced33Active
$290,000
2 bd · 2 ba · 1,072 sqft
4008 Whispering Hills Drive, Chester, NY
Karen R Taphorn · Howard Hanna Rand Realty

Price Reduced24Active
$275,000
2 bd · 1 ba · 1,084 sqft
2113 Whispering Hills, Chester, NY
Valerie Quinn · Keller Williams Realty

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively 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. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Chester housing market

July 2026 · This period is still settling

Homes that sold · County records, as of Jul 30, 2026

Median sale price: $452,999$342,000–$676,250 typical range
Price per sq. ft.: $277
Sales: 14
Paid in cash: 21.4%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $750,000
Homes for sale: 64

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: 20.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 2,098 sq. ft.

Chester, NY community profile

Population: 4,099
Median income: $110,682
Housing units: 1,761
People per sq. mi.: 120.2
Area: 34.1 sq. mi.

Source: HJN community data

Explore Chester homes

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively 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. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Multi-family homes

Co-ops

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Chester, NY community profile

Population: 4,099
Median income: $110,682
Housing units: 1,761
People per sq. mi.: 120.2
Area: 34.1 sq. mi.

Source: HJN community data

Chester housing market

July 2026 · This period is still settling

Homes that sold · County records, as of Jul 30, 2026

Median sale price: $452,999$342,000–$676,250 typical range
Price per sq. ft.: $277
Sales: 14
Paid in cash: 21.4%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $750,000
Homes for sale: 64

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: 20.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 2,098 sq. ft.

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Your local brokerage

Listing data & MLS disclosures

Chester housing market

Homes that sold · County records, as of Jul 30, 2026

Homes on the market · MLS, as of Jul 21, 2026

Price trend · Assessor repeat sales, as of Jul 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Chester, NY community profile

Explore Chester homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Chester, NY community profile

Chester housing market

Homes that sold · County records, as of Jul 30, 2026

Homes on the market · MLS, as of Jul 21, 2026

Price trend · Assessor repeat sales, as of Jul 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026