24

Homes for Sale near Chester Elementary School

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  • /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
  • /9

    $369,900

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

    3910 Whispering Hills, Chester, NY 10918

    Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

    Agent Photo

    Randolph Rogers

    eXp Realty

    (845) 957-9249

    3910 Whispering Hills, Chester, NY 10918
  • /2

    $425,000 Open Sun 12PM - 2PM

    • 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
  • /8

    $699,990

    • 4 Beds
    • 3 Baths
    • 1,867 Sq Ft

    34 Mountainside Dr, Chester, NY 10918

    ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
  • /47

    $799,999 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Brand new to the market! This spectacular spacious colonial has room for everyone! Perched at the top of the Fieldcrest subdivision with sweeping views that can’t be missed you will find this property that offers something for everyone.Set on 1.3 picturesque acres in a desirable neighborhood, this beautifully maintained home offers the perfect blend of comfort, space, and functionality. Enjoy

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /50

    $699,000

    • 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
  • /31

    $649,999

    • 5 Beds
    • 6 Baths
    • 3,568 Sq Ft

    7 Cherrywood Dr, Goshen, NY 10924

    This beautiful, spacious contemporary split-level home is perfect for the in-laws, featuring a separate apartment. The main house boasts 5 bedrooms and 4 bathrooms, with an entrance foyer leading to a large entertaining room with Fireplace. From there, you can move into the media room and then onto separate entrance to pool areaOn the main level, features hardwood floors threw out home. Large

    Joseph Brown RE/MAX Real Property Group

    7 Cherrywood Dr, Goshen, NY 10924
  • /8

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 2,603 Sq Ft

    32 Mountainside Dr, Chester, NY 10918

    A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • /30

    $550,000

    • 5 Beds
    • 2.5 Baths
    • 1,815 Sq Ft

    208 Glenmere Rd, Chester, NY 10918

    Welcome to 208 Glenmere Rd, Chester, NY! This charming country home, nestled on picturesque grounds, is now available for sale. The main level features an eat-in kitchen, a formal dining room, and two spacious bedrooms, while the upper level offers three additional bedrooms. The newly renovated cottage boasts new flooring, windows, kitchen, and heating system. The interior has been freshly

    David Kraus MK Realty Inc

    208 Glenmere Rd, Chester, NY 10918
  • /5

    $259,000

    • Land
    • 20.18 Acres
    • $12,834 per Acre

    32 Mountainside Dr, Chester, NY 10918

    A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • /50

    $1,195,000

    • 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

    $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
  • /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
  • /31

    $389,000

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

    1221 Whispering Hills, Chester, NY 10918

    Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! 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

    Malia Leonard BUY NY REALTY LLC

    1221 Whispering Hills, Chester, NY 10918
  • /9

    $149,900

    • Land
    • 8,873 Sq Ft
    • $735,886 per Acre

    2 Imperial Park, Chester, NY 10918

    Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

    William Scolza HomeSmart Homes & Estates

    2 Imperial Park, 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
  • /33

    $260,000

    • 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
  • /3

    $650,000

    • Land
    • 2 Acres
    • $325,000 per Acre

    50 Elkay Dr, Chester, NY 10918

    Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

    Leib Glanz Point Realty USA

    50 Elkay Dr, Chester, NY 10918
  • /29

    $529,900 Open Sun 1PM - 3PM

    • 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
  • /23

    $410,000

    • 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
  • /32

    $319,900

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

    2820 Whispering Hills, Chester, NY 10918

    Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

    Anne Marie Scouarnec R2M Realty Inc.

    2820 Whispering Hills, Chester, NY 10918
  • /32

    $344,900

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

    1311 Whispering Hills Unit 96, Chester, NY 10918

    Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

    Michael Jenney Keller Williams Realty

    1311 Whispering Hills Unit 96, Chester, NY 10918
  • /8

    $225,000

    • Land
    • 1 Acre
    • $225,000 per Acre

    34 Mountainside Dr, Chester, NY 10918

    Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at Sugar

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
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