22

Homes for Sale near Chester Elementary School

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  • /37

    $789,900

    Open Sat 12PM - 2PM
    • 5 Beds
    • 4 Baths
    • 4,697 Sq Ft

    19 Grand View Terrace, Chester, NY 10918

    Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living

    Agent Photo

    Randolph Rogers

    eXp Realty

    19 Grand View Terrace, Chester, NY 10918
  • /50

    $1,000,000

    • 4 Beds
    • 2.5 Baths
    • 3,955 Sq Ft

    1 Oakland Ave, Chester, NY 10918

    Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    1 Oakland Ave, Chester, NY 10918
  • /50

    $370,000

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

    3815 Whispering Hills Dr, Chester, NY 10918

    Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

    David Kraus MK Realty Inc

    3815 Whispering Hills Dr, Chester, NY 10918
  • /47

    $469,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    20 Cherrywood Dr, Goshen, NY 10924

    Well Maintained 3 Bedroom 2 Full Bath Ranch in Goshen Town with Chester Schools on a corner lot. The Front Porch with trex decking leads to a beautiful double door entry. Primary Suite includes a full bath with a nice tiled shower. The Living room has hardwood floors with natural light from large window and leads to Dining area and Kitchen. Additional room near Kitchen can be used as eat in

    Frank Cafarchio Keller Williams Realty

    20 Cherrywood Dr, Goshen, NY 10924
  • /23

    $390,000

    • 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
  • /35

    $879,999

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,236 Sq Ft

    24 Boville Ct, Chester, NY 10918

    Welcome to 24 Boville Court, a beautifully situated home tucked away on a quiet cul-de-sac in the desirable Town of Chester. Offering a wonderful blend of comfort, privacy, and convenience, this property is the perfect place to call home. Step inside to discover bright and inviting living spaces, generously sized rooms, and a functional floor plan designed for both everyday living and

    Jennifer Acevedo KW Hudson Valley United

    24 Boville Ct, Chester, NY 10918
  • /50

    $1,145,000

    $50K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

    Beth Palma Keller Williams Realty

    19 High St, 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
  • /43

    $430,000

    $20K PRICE DROP
    • 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
  • /49

    $769,000

    $31K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Price improvement! Wait until you see all this home has to offer! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /29

    $549,900

    • 3 Beds
    • 2 Baths
    • 2,138 Sq Ft

    3318 State Route 94, Chester, NY 10918

    This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the

    Asha Keegan Howard Hanna Rand Realty

    3318 State Route 94, Chester, NY 10918
  • /22

    $570,000

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,968 Sq Ft

    2 Sycamore Ln, Goshen, NY 10924

    Charming Split-Level fenced in property located in the highly sought-after Chester School District in Goshen, New York. Don't miss the opportunity to preview this beautiful home featuring an open and inviting floor plan designed for comfortable everyday living and entertaining. Step outside to a spacious rear yard complete with an above-ground pool and gazebo, creating the perfect setting for

    Jeanette Santory Howard Hanna Rand Realty

    2 Sycamore Ln, Goshen, NY 10924
  • /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
  • /28

    $579,999

    • 4 Beds
    • 2.5 Baths
    • 2,698 Sq Ft

    24 Walnut St, Chester, NY 10918

    Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

    Tara Roufanis Keller Williams Village Sq Rlt

    24 Walnut St, Chester, NY 10918
  • /39

    $365,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2703 Whispering Hills, Chester, NY 10918

    Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the

    Rebecca Matta-Candela Keller Williams Realty

    2703 Whispering Hills, Chester, NY 10918
  • /33

    $260,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, Chester, NY 10918
  • /40

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,730 Sq Ft

    37 Surrey Rd, Chester, NY 10918

    Looking for a 4-bed home in Chester, NY with a pool, major system updates, generous outdoor living space, and convenient access to schools, parks, shopping, and commuter routes? Welcome to 37 Surrey Road, a beautifully maintained raised ranch offering 4 bedrooms, 2 full bathrooms, approximately 1,730 square feet of living space, and a backyard designed for entertaining and relaxation. Set on a

    Lady Castro eXp Realty

    37 Surrey Rd, Chester, NY 10918
  • /29

    $499,900

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,032 Sq Ft

    35 Maple Ave, Chester, NY 10918

    Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances,

    Joanne Timperio RE/MAX Benchmark Realty Group

    35 Maple Ave, Chester, NY 10918
  • /26

    $399,900

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    Great new price! Come take a look at 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

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • /50

    $599,000

    $251K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    558 Pine Hill Rd, Chester, NY 10918

    Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

    Charnie Guttmann eRealty Advisors, Inc

    558 Pine Hill Rd, Chester, NY 10918
  • /29

    $720,000

    • 4 Beds
    • 2.5 Baths
    • 1,718 Sq Ft

    26 Bridle Ln, Chester, NY 10918

    From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

    David White Owner Entry.com

    26 Bridle Ln, Chester, NY 10918
  • /38

    $579,999

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    3 Elmwood Dr, Goshen, NY 10924

    MOVE-IN READY BI-LEVEL AVAILABLE IN GOSHEN/CHESTER AREA! If you're searching for an exceptional home in the desirable Goshen/Chester area with low property taxes, this beautifully updated bi-level is a must-see. Renovated in 2022 and offering nearly 2,000 square feet of meticulously maintained living space, this home combines modern style with everyday comfort. Step inside to discover beautifully

    Vincent McAteer Terrie OConnor

    3 Elmwood Dr, Goshen, NY 10924
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