4 Bedroom Homes in Chester, NY

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3 beds New construction With a pool

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24 of 36 Listings

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4 Bedroom Homes in Chester, NY

24 of 36 Listings

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36 listings

4 Bedroom Homes in Chester, NY

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24 of 36 Listings

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4 Bedroom Homes in Chester, NY

24 of 36 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

43

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Active

$825,000

4 bd · 4 ba · 3,054 sqft

330 Stone Bridge Road, Chester, NY

Barbara Kearney · Hunt Real Estate ERA

50Active

$749,000

4 bd · 3 ba · 2,599 sqft

121 Conklingtown Road, Chester, NY

Chaim Weiss · MS Realty Group USA, Inc

31Active

$1,899,000

4 bd · 3 ba · 1,782 sqft

68 Birchwood Drive, Chester, NY

Barbara Kearney · Hunt Real Estate ERA

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

49Active

$700,000

4 bd · 3 ba · 3,296 sqft

13 Bianca Boulevard, Chester, NY

Theresa M Powers · Keller Williams Realty

30Active

$750,000

4 bd · 3 ba · 2,280 sqft

1 Sanford Avenue, Chester, NY

Danielle R. Hinton · Redfin Real Estate

19Active

$459,000

4 bd · 3 ba · 2,060 sqft

63 Hubshop Road, Chester, NY

Ryan Barrett · Keller Williams Realty

Price Reduced39Active

$475,000

4 bd · 2 ba · 1,820 sqft

32 Surrey Road, Chester, NY

Ammar Iqbal · eXp Realty

46Active

$839,000

4 bd · 4 ba · 2,707 sqft

34 Boville Court, Chester, NY

Jillian Laga · Keller Williams Valley Realty

36Active

$749,900

4 bd · 4 ba · 3,080 sqft

20 Mountainside Drive, Chester, NY

Randolph Rogers · eXp Realty

50Active

$799,000

4 bd · 3 ba · 2,516 sqft

3 Garnett Hill Road, Chester, NY

Jacob Fried · Keller Williams Realty

38Active

$585,000

4 bd · 2 ba · 1,948 sqft

548 White Schoolhouse Road, Chester, NY

Carol Monroe · Najer Realty

Price Reduced35Active

$459,900

4 bd · 3 ba · 1,990 sqft

3001 Schroon River Road, Chester, NY

Jonathan Minerick · Homecoin.com

Price Reduced39Active

$449,500

4 bd · 3 ba · 2,058 sqft

7 May Road, Chester, NY

Jennifer Ball · Hunt ERA

Price Reduced36Active

$475,500

4 bd · 2 ba · 1,369 sqft

7189 US. 9, Chester, NY

Julia Pucciarelli · Gallo Realty ADK Inc

Price Reduced16Active

$299,000

4 bd · 1 ba · 1,504 sqft

151 Main Street, Chester, NY

Eveline R White · Hudson Valley Griffith

29Active

$549,999

4 bd · 3 ba · 2,098 sqft

7 Lakeview Drive, Chester, NY

Sheyla L. Falesto · Howard Hanna Rand Realty

36Active

$799,000

4 bd · 3 ba · 3,070 sqft

197 Oxford Road, Chester, NY

Regina Carmel · Howard Hanna Rand Realty

Price Reduced35Active

$349,999

4 bd · 2 ba · 1,560 sqft

241 Meadow Avenue, Chester, NY

Chativa Bowen · Keller Williams Realty

Price Reduced40Active

$634,999

4 bd · 3 ba · 2,316 sqft

424 Laroe Road, Chester, NY

Jeffrey Morrissey · Epique Realty

Price Reduced36Active

$750,000

4 bd · 4 ba · 3,100 sqft

985 Craigville Road, Chester, NY

David Deberardinis · Serhant LLC

47Active

$699,900

4 bd · 3 ba · 3,977 sqft

342-346 Starbuck Hill Road, Chester, NY

Holly Dansbury · Davies Davies & Associates Real Estate LLC

50Active

$1,195,000

4 bd · 4 ba · 4,281 sqft

22 Goshen Road, Chester, NY

Martha Randazzo · Howard Hanna Rand Realty

35Active

$875,000

4 bd · 3 ba · 3,656 sqft

49 Stone Mountain Trail, Chester, NY

Arya Rabinovits · eRealty Advisors, Inc

Price Reduced50Active

$990,000

4 bd · 3 ba · 3,955 sqft

1 Oakland Avenue, Chester, NY

Christina Rowan · Howard Hanna Rand Realty

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 15:37:50 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 15:37:50 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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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