5 Bedroom Homes in Chester, NY

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3 beds New construction With a pool

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13 Listings

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5 Bedroom Homes in Chester, NY

13 Listings

38Active

13 listings

5 Bedroom Homes in Chester, NY

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13 Listings

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5 Bedroom Homes in Chester, NY

13 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

38Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$699,000

5 bd · 4 ba · 3,463 sqft

65 Oxford Springs Road, Chester, NY

Stephanie Dolan · HomeSmart Homes & Estates

1Active

$750,000

5 bd · 3 ba · 2,700 sqft

3 Hilltop Lane, Chester, NY

Moshe Kaufman · MK Realty Inc

1Active

$750,000

5 bd · 3 ba · 2,700 sqft

1 Hilltop Lane, Chester, NY

Moshe Kaufman · MK Realty Inc

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Price Reduced28Active

$320,000

5 bd · 2 ba · 1,286 sqft

20 Vetter Avenue, Chester, NY

Julia Pucciarelli · Gallo Realty ADK Inc

3Active

$750,000

5 bd · 3 ba · 2,700 sqft

2 Hemlock Court, Chester, NY

Moshe Kaufman · MK Realty Inc

Price Reduced56Active

$899,000

5 bd · 3 ba · 2,482 sqft

190 Kingsley Ln Ext, Chester, NY

Brooke Clark · Four Seasons Sothebys International Realty

5Active

$850,000

5 bd · 3 ba · 3,200 sqft

5 Hilltop Lane, Chester, NY

Moshe Kaufman · MK Realty Inc

50Active

$750,000

5 bd · 3 ba · 2,700 sqft

3 Hemlock Court, Chester, NY

Dovid Hoffman · MK Realty Inc

37Active

$789,900

5 bd · 4 ba · 4,697 sqft

19 Grand View Terrace, Chester, NY

Randolph Rogers · eXp Realty

Price Reduced49Active

$785,000

5 bd · 6 ba · 5,403 sqft

4 Debbie Court, Chester, NY

Joseph Rosenfeld · Flag Realty Group

35Active

$999,999

5 bd · 3 ba · 4,772 sqft

2 Garnett Hill Road, Chester, NY

Rachel L Baruchov · Platinum Realty Associates

48Active

$1,100,000

5 bd · 4 ba · 5,312 sqft

53 Gibson Hill Road, Chester, NY

Ammar Iqbal · eXp Realty

Price Reduced34Active

$949,000

5 bd · 4 ba · 3,136 sqft

12 Damian Court, Chester, NY

Elimelech Kremer · MS Realty Group USA, Inc

Listing data & MLS disclosures

Global MLS: IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.
Listing information ©2026 Local REALTOR® - Douglas Perlson, Corp. Broker - (646) 315-9116. All Rights Reserved. Last Updated: 2026-09-01 22:35:36 UTC
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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Listing data & MLS disclosures

Global MLS: IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.
Listing information ©2026 Local REALTOR® - Douglas Perlson, Corp. Broker - (646) 315-9116. All Rights Reserved. Last Updated: 2026-09-01 22:35:36 UTC
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, 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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Registered offenders on the map

Your local brokerage

Your local brokerage

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

Your local brokerage

Listing data & MLS disclosures

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