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Modern Homes for Sale in Chester, NY

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  • /50

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft

    1 Bell Way, Chester, NY 10918

    COLOR AT THE CURB. A POP OF PERSONALITY AT THE DOOR. FROM THE FIRST HELLO, THIS ONE FEELS LIKE HOME.Before you even step inside, this home makes a memorable first impression. The perennial garden, natural stone walkway, and inviting front door adds just the right pop of color and personality, setting the tone for a home that feels fresh, welcoming and anything but cookie-cutter. Tucked away

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    1 Bell Way, Chester, NY 10918
  • /38

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,711 Sq Ft

    63 Whitetail Run, Chester, NY 10918

    This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

    Artan Kukaj SPIRAL NY Real Estate LLC

    63 Whitetail Run, Chester, NY 10918
  • /40

    $634,999

    $15K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,316 Sq Ft

    424 Laroe Rd, Chester, NY 10918

    Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.

    Jeffrey Morrissey Epique Realty

    424 Laroe Rd, Chester, NY 10918
  • /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
  • /36

    $750,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    985 Craigville Rd, Chester, NY 10918

    Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

    DAVID DEBERARDINIS Serhant LLC

    985 Craigville Rd, Chester, NY 10918
  • /20

    $894,000

    $105K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,535 Sq Ft

    220 Oxford Rd, Chester, NY 10918

    220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

    Moche Halpern Blooming Realty

    220 Oxford Rd, Chester, NY 10918
  • /50

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    66 Whitetail Run, Chester, NY 10918

    Welcome to 66 Whitetail Run – Chester, NY.Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities.Step inside to a

    Soleil Jackman Howard Hanna Rand Realty

    66 Whitetail Run, Chester, NY 10918
  • /50

    $3,400,000

    • 4 Beds
    • 4 Baths
    • 7,750 Sq Ft

    19 Greentree Ln, Chester, NY 10918

    Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

    Jake Garay Serhant LLC

    19 Greentree Ln, Chester, NY 10918
  • /34

    $650,000

    • 3 Beds
    • 4 Baths
    • 2,520 Sq Ft

    29 Murray Dr, Chester, NY 10918

    Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances

    Liudmila Lobeeva eXp Realty

    29 Murray Dr, Chester, NY 10918
  • /35

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 3,656 Sq Ft

    49 Stone Mountain Trail, Chester, NY 10918

    Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

    Arya Rabinovits eRealty Advisors, Inc

    49 Stone Mountain Trail, Chester, NY 10918
  • /2

    $649,999

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 2,902 Sq Ft

    3561 State Route 94, Chester, NY 10918

    Showings begin on 8/28. More information and pics coming soon.

    Gina Dudgeon Howard Hanna Rand Realty

    3561 State Route 94, Chester, NY 10918
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