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5-Bedroom Homes for Sale in Chester, NY

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  • /50

    $849,900

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft

    284 Bull Mill Rd, Chester, NY 10918

    Monroe's Stunning Mini Mansion Awaits Its New Owner!This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase.Before heading upstairs, prepare to be impressed by the spacious chef's

    Jayne Mangieri Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
  • /37

    $675,000 Open Sat 11AM - 2PM

    • 5 Beds
    • 3 Baths
    • 2,983 Sq Ft

    9 Mount Ridge Ct, Monroe, NY 10950

    Tucked away on a peaceful cul-de-sac, this lovingly maintained 5-bedroom, 3-full-bath home offers 3,000 square feet of light-filled living space and a layout designed for comfort and flexibility. Owned by the original homeowner since day one, this property has been thoughtfully cared for and is ready for its next chapter.Inside, you’ll find big, bright rooms and an easy flow perfect for

    James Feldhaus eXp Realty

    9 Mount Ridge Ct, Monroe, NY 10950
  • /45

    $650,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 3,617 Sq Ft

    65 Oxford Springs Rd, Chester, NY 10918

    Welcome to 65 Oxford Springs Road, Chester, NY, a one-of-a-kind custom-built Country Contemporary home perfectly set on a private 2.3-acre hilltop. This unique property offers a rare blend of privacy, space, and convenience, just minutes from the NYS Thruway, nearby state parks, and only 45 minutes to New York City.The bright, open floor plan is designed to welcome natural light into

    Ammar Iqbal eXp Realty

    65 Oxford Springs Rd, Chester, NY 10918
  • /35

    $1,700,000

    • 10 Beds
    • 6.5 Baths
    • 3,512 Sq Ft

    17 Bonnie Brook Rd, Monroe, NY 10950

    Over 20 sprawling acres with serene life, pond frontage, this is a true sanctuary. Located in Monroe-Woodbury this unique property offer two distinct residences and a spacious barn, providing endless possibilities. House 1: Contemporary Modern originally built in 1965. The first home boasts a generous 3,500+ sq ft of premium living space. Designed with a flexible layout, the home features two

    Pamela Henning Keller Williams Hudson Valley

    17 Bonnie Brook Rd, Monroe, NY 10950
  • /50

    $2,800,000

    • 16 Beds
    • 11 Baths
    • 7,511 Sq Ft

    10 Damien Ct, Chester, NY 10918

    Don't miss this incredible opportunity to own 10 & 12 Damien Court, two stunning custom homes being sold together on nearly 6 acres of beautifully landscaped grounds located on a peaceful cul-de- sac of Chester.Together offering 16 bedrooms and 11 baths, these homes are perfect for multigenerational living, extended families, or investment potential. Enjoy gourmet eat-in kitchens, private suites,

    Elimelech Kremer MS Realty Group USA, Inc

    10 Damien Ct, Chester, NY 10918
  • /45

    $700,000 Open House 8/09

    • 5 Beds
    • 2.5 Baths
    • 3,115 Sq Ft

    507 Bull Mill Rd, Chester, NY 10918

    Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design.Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both

    Alison Orlando Keller Williams Hudson Valley

    507 Bull Mill Rd, Chester, NY 10918

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$565,000
Median Single Family Sale Price
$565,000
Median 2 Bedroom Sale Price
$345,000
Average Price Per Sq Ft
$268
Number of Homes for Sale
1
Last 12 months Home Sales
37
Months of Supply
0.30
Median List Price
$574,900
Median Change From 1st List Price
13%
Median Home Sale Price YoY Change
-26%
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