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Chester, NY Townhomes for Sale

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  • /22

    $345,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    65 Darin Rd, Warwick, NY 10990

    Charming and move-in ready townhouse in desirable Kings Estates of Warwick, NY, located in the Warwick Valley Central School District with no HoA fees and 60 mins to/from NYC. This cozy 3-bedroom, 2.5-bath home offers an open-concept living and dining area filled with natural light. The updated kitchen boats stainless steel appliances, offering a modern touch to this warm and inviting home. A

    Sandra Laramore Redfin Real Estate

    65 Darin Rd, Warwick, NY 10990
  • /34

    $299,999

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

    2317 Whispering Hills, Chester, NY 10918

    Welcome to your new home at 2317 Whispering Hills, Chester, NY 10918, where resort-style living meets suburban charm! This meticulously updated property offers an incredible opportunity to enjoy a life of comfort and convenience.This delightful 2-bedroom, 1.5-bathroom home has been thoughtfully renovated from top to bottom. The kitchen is a chef's dream with brand-new stainless steel

    Jeffrey Morrissey HomeSmart Homes & Estates

    2317 Whispering Hills, Chester, NY 10918
  • /22

    $295,000

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

    3708 Whispering Hills, Chester, NY 10918

    Welcome to this fantastic 2-bedroom, 1.5-bathroom condo, perfectly situated in the desirable Whispering Hills community. This unit offers a perfect blend of comfort and convenience, with an array of amenities that make everyday living a breeze. Step inside and discover a spacious, bright living area that flows seamlessly into the dining space. The updated kitchen is a true highlight, featuring

    Nikki Grzegorzewski Keller Williams Realty

    3708 Whispering Hills, Chester, NY 10918
  • /34

    $369,000

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

    3915 Whispering Hills, Chester, NY 10918

    Highly desirable 3 BR, 2.5 Bath w/2 car garage condo in Whispering Hills! Pristine Condition! Nothing to do but move in! End Unit and Largest Unit in the complex! Great Location! Updated kitchen and baths, flooring, carpet, garage door! This Condo of distinction boasts an Open Floor Plan, Cathedral Ceilings, Skylight, Wood-Burning Fireplace, Central Air, Primary Bedroom w/Full Bath, Private Patio

    Kristie Jacques Century 21 Full Service Realty

    3915 Whispering Hills, Chester, NY 10918
  • /26

    $357,000

    • 3 Beds
    • 2.5 Baths
    • 1,316 Sq Ft

    2503 Whispering Hills, Chester, NY 10918

    PRICE REDUCED NEED TO SELL!!! Motivated Seller -- Discover this beautiful 3-bedroom, 2.5-bath duplex offering 1,316 sq ft of comfortable living in the highly desirable Whispering Hills condo community in Chester, NY. Enjoy great outdoor space, perfect for relaxing or entertaining. Ideal for commuters with easy access to major highways, and located within the sought-after Chester School District.

    Sonia Gonzalez Keller Williams Hudson Valley

    2503 Whispering Hills, Chester, NY 10918
  • /2

    $349,900

    • 3 Beds
    • 1.5 Baths
    • 1,376 Sq Ft

    264 Heritage Ln, Monroe, NY 10950

    Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

    Frank Golio Howard Hanna Rand Realty

    264 Heritage Ln, Monroe, NY 10950
  • /21

    $390,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    51 Darin Rd, Warwick, NY 10990

    Whether you're downsizing or searching for your perfect home, this affordable townhome in beautiful Warwick, NY offers a blend of comfort, functionality, and lifestyle. Located in a vibrant neighborhood with no HOA fees, you'll enjoy convenient access to shopping, transportation, and the charm of a close-knit community.Step inside to find an open-concept first floor where a modern kitchen

    Anthony Spadaro RE/MAX Benchmark Realty Group

    51 Darin Rd, Warwick, NY 10990
  • /27

    $385,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    36 Marian Ct, Warwick, NY 10990

    Turnkey Townhome with Scenic Views – No HOA – Warwick School District. Welcome to your newly renovated 2-bedroom, 1.5-bath townhome in the heart of Warwick, just 60 minutes from NYC. This beautifully updated home is perfect for first-time buyers or anyone seeking a stylish, low-maintenance lifestyle in a quiet, commuter-friendly setting—without the restrictions of an HOA. Set against a backdrop

    Courtney Tablante Keller Williams Realty

    36 Marian Ct, Warwick, NY 10990

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$526,000
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$315,000
Median 2 Bedroom Sale Price
$295,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$265
Number of Homes for Sale
26
Last 12 months Home Sales
135
Months of Supply
2.30
Median List Price
$574,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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