12

Chester, NY Homes for Sale under $500,000

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  • /44

    $450,000

    • 4 Beds
    • 2 Baths
    • 1,642 Sq Ft

    82 Southside Dr, Monroe, NY 10950

    Welcome to 82 Southside Dr in Monroe — a beautifully renovated ranch-style home offering effortless one-level living in the highly sought-after Monroe-Woodbury School District. This 4-bedroom, 2-bath home features a versatile layout with an additional home office or den, ideal for remote work, a playroom, or guest space. Fully renovated from top to bottom, the home showcases brand-new flooring

    Agent Photo

    Ammar Iqbal

    eXp Realty

    (329) 214-0985

    82 Southside Dr, Monroe, NY 10950
  • /32

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    5 Roggia Rd, Chester, NY 10918

    Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and

    Agent Photo

    Nazma Sooknanan

    Nazma Real Estate LLC

    (845) 606-3972

    5 Roggia Rd, Chester, NY 10918
  • /2

    $425,000

    Open Sun 12PM - 2PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2722 Whispering Hills Unit 542, Chester, NY 10918

    New beginnings offered in this light and bright completely updated end unit featuring two car garage, brand new floors, freshly painted, update kitchen with new stainless steel appliances and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village

    Agent Photo

    Erin Connolly-Frontino

    Artisan Realty

    (845) 932-1237

    2722 Whispering Hills Unit 542, Chester, NY 10918
  • /43

    $450,000

    • 3 Beds
    • 1.5 Baths
    • 1,177 Sq Ft

    151 Laroe Rd, Chester, NY 10918

    What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional

    Todd Sullivan Keller Williams Realty

    151 Laroe Rd, Chester, NY 10918
  • /13

    $460,000

    • 3 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    1367 Kings Hwy, Chester, NY 10918

    Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

    Mark Karten Karten Real Estate Svcs LLC

    1367 Kings Hwy, Chester, NY 10918
  • /48

    $485,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    35 Maple Ln, Monroe, NY 10950

    Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

    Kewin Garabito eXp Realty

    35 Maple Ln, Monroe, NY 10950
  • /28

    $500,000

    • 3 Beds
    • 2 Baths
    • 2,688 Sq Ft

    5 N Hudson St Unit N, Chester, NY 10918

    3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

    Bernadette Corrigan Keller Williams Realty

    5 N Hudson St Unit N, Chester, NY 10918
  • /23

    $400,000

    $55K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,561 Sq Ft

    33 Meadow Ave, Chester, NY 10918

    One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

    Ernie Acampora River Realty Services, Inc.

    33 Meadow Ave, Chester, NY 10918
  • /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • /27

    $499,900

    Open Sat 12PM - 2PM $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    11 Oxford Depot, Chester, NY 10918

    Welcome to 11 Oxford Depot Rd, Chester, NY — a unique 3-bedroom, 2-bath home that perfectly blends charm, space, and modern updates. Featuring beautiful hardwood floors throughout, multiple living and entertaining areas, spacious bedrooms, updated bathrooms, and flexible bonus space ideal for a home office, playroom, or guest setup. The finished lower level adds even more versatility with

    Aneudy Rosa Keller Williams Realty

    11 Oxford Depot, Chester, NY 10918
  • /23

    $410,000

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    This 2 bedroom charmer with additional room offers potential 3 bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • /37

    $405,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    58 Darin Rd, Warwick, NY 10990

    Welcome to this beautifully renovated townhome offering the perfect blend of modern upgrades, natural light, and low-maintenance living in one of the Hudson Valley’s most desirable communities. Step inside to discover gleaming hardwood floors, an open and inviting layout, and a sun-filled living space designed for both comfort and entertaining. The updated kitchen features stainless steel

    Melissa Forsyth Hudson Valley Home Connection

    58 Darin Rd, Warwick, NY 10990

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$501,500
Median Single Family Sale Price
$665,000
Median Townhouse Sale Price
$337,450
Median 2 Bedroom Sale Price
$307,500
Average Price Per Sq Ft
$275
Number of Homes for Sale
44
Last 12 months Home Sales
91
Months of Supply
5.80
Median List Price
$549,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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