12

Chester, NY Homes for Sale under $400,000

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  • /20

    $360,000

    • 3 Beds
    • 1.5 Baths
    • 1,460 Sq Ft

    4 Maple Ln, Monroe, NY 10950

    If you possess talent and intelligence, this is your moment! Attention First time homebuyers and astute investors! Seize this opportunity to improve this charming Fixer upper home. With a little tender loving care, it can be wonderful once more. Situated in a fantastic area, with all amenities nearby. With some effort you can enjoy the benefits forever!

    Joseph Rosenfeld Flag Realty Group

    4 Maple Ln, Monroe, NY 10950
  • /23

    $400,000

    • 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
  • /36

    $395,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    223 Eagleton Dr, Monroe, NY 10950

    Welcome home to this tastefully updated and meticulously maintained 3 bedroom, 2.5 bath unit in a highly sought after community in the Monroe Woodbury school district. The Windridge community is clustered around ponds adding to the country feel. Located near the back of the cul-de-sac, this home features an open floorplan for easy living and entertaining. Step out of the sliding door in the

    Theresa Powers Keller Williams Realty

    223 Eagleton Dr, Monroe, NY 10950
  • /39

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • /31

    $397,000

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    1221 Whispering Hills, Chester, NY 10918

    Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural light, this home blends modern upgrades with functional design. Once you step inside, you will discover brand new

    Malia Leonard BUY NY REALTY LLC

    1221 Whispering Hills, Chester, NY 10918
  • /11

    $349,999

    • Land
    • 4.9 Acres
    • $71,428 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

    James Feldhaus eXp Realty

    8 Camelback Rd, Chester, NY 10918
  • /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • /28

    $305,000

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    3917 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

    Jie Liu Keller Williams Hudson Valley

    3917 Whispering Hills, Chester, NY 10918
  • /38

    $350,000

    • 2 Beds
    • 1 Bath
    • 1,272 Sq Ft

    307 Gibson Hill Rd, Chester, NY 10918

    Looking for a solid built home with great bones and a lot of space in the Warwick School District? This spacious ranch home is waiting for your modern touches. Built strong, this home is in need of some cosmetic updates but you can live in the home and enjoy it as you go. This home offers 2 bedrooms (plus a den) and a full bath. The kitchen makes every square inch count with ample storage and

    Donna Gennaro Howard Hanna Rand Realty

    307 Gibson Hill Rd, Chester, NY 10918
  • /14

    $370,000

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2203 Whispering Hills, Chester, NY 10918

    Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

    Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
  • /2

    $350,000

    • Land
    • 5.7 Acres
    • $61,404 per Acre

    552 Pine Hill Rd, Chester, NY 10918

    Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

    Charnie Guttmann eRealty Advisors, Inc

    552 Pine Hill Rd, Chester, NY 10918
  • /4

    $350,000

    • Land
    • 5.1 Acres
    • $68,627 per Acre

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

    Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

    Theresa Powers Keller Williams Realty

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$505,000
Median Single Family Sale Price
$620,000
Median Townhouse Sale Price
$327,500
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
32
Last 12 months Home Sales
105
Months of Supply
3.70
Median List Price
$520,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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