18

Homes for Sale near Chester Academy - Middle/High School

Section Image Section Image
  • /30

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    2812 Whispering Hills Unit 577, Chester, NY 10918

    Motivated sellers. Welcome to Whispering Hills, one of the most sought-after communities in the area with resort style amenities and unbeatable commuter convenience. Picture yourself coming home to this beautiful space. The large living room opens to sliding glass doors that lead out to your private deck, the perfect spot to unwind after a long day. Cathedral ceilings create an open, airy feel,

    Agent Photo

    Kathy White

    Exit Realty Connections

    (845) 390-2310

    2812 Whispering Hills Unit 577, Chester, NY 10918
  • /28

    $515,000

    • 4 Beds
    • 2.5 Baths
    • 2,898 Sq Ft

    25 High St, Chester, NY 10918

    25 High Street is back on the market and newly refreshed, making this Victorian gem more inviting than ever. Brimming with character and ready for your personal touch, this special home welcomes you with original wide-plank wood floors throughout—preserved under carpeting to maintain their timeless authenticity and warmth. Entertain in style in the bright, modern kitchen or host memorable

    Agent Photo

    Alicia Goldman

    Christie's Int. Real Estate

    (845) 244-4823

    25 High St, Chester, NY 10918
  • /27

    $500,000

    • 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
  • /35

    $489,000

    • 3 Beds
    • 1.5 Baths
    • 1,284 Sq Ft

    27 Cherrywood Dr, Goshen, NY 10924

    (LOW TAXES) Welcome to this Beautifully maintained, and charming 3-bedroom, 2-bath home perfectly situated in the heart of Goshen. This inviting property offers the ideal combination of comfort, space, and convenience. Step inside to find a bright and open layout filled with natural light. The spacious living area flows seamlessly into a well-appointed kitchen and dining space — ideal for

    Kevin Grier Keller Williams Hudson Valley

    27 Cherrywood Dr, Goshen, NY 10924
  • /23

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

    Kassandra Mott Keller Williams Hudson Valley

    70 Main St, 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.).

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
  • /17

    $339,900

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

    1503 Whispering Hills, Chester, NY 10918

    Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground and tennis across the street, pool, clubhouse and bus

    Darlene Provino Century 21 E & M Williams Rlty

    1503 Whispering Hills, Chester, NY 10918
  • /33

    $295,000

    • 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
  • /33

    $369,900

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    18 Oakland Ave, Chester, NY 10918

    This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door." There is a large shed in the backyard, all near all the activities the Village has to offer.

    Claude Brischoux Keller Williams Realty

    18 Oakland Ave, Chester, NY 10918
  • /24

    $345,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    65 Hudson St, Chester, NY 10918

    A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure

    Nikki Grzegorzewski Keller Williams Realty

    65 Hudson St, Chester, NY 10918
  • /40

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 3,627 Sq Ft

    1 Jessica Ct, Goshen, NY 10924

    You’ll feel it the moment you pull into 1 Jessica Court — a sense that very few homes carry: new-home energy, thoughtful layout, and a location that mediates between calm and connection. Built in 2017, this colonial still has the glow of modern craftsmanship: systems built to last, clean lines, and finishes you won’t feel inclined to upgrade. But the magic is how naturally it molds itself to your

    Alex Mashkin Keller Williams Realty Partner

    1 Jessica Ct, 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
  • /28

    $1,498,888

    • 4 Beds
    • 4 Baths
    • 7,308 Sq Ft

    37 Main St, Chester, NY 10918

    Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features:•

    James Feldhaus eXp Realty

    37 Main St, 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
  • /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

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
  • /4

    $350,000

    • Land
    • 5.4 Acres
    • $64,815 per Acre

    2 Virginia Ln, Goshen, NY 10924

    Town of Goshen 3 commercial lots with road frontage. Selling all 3 lots together. Most likely lot 2 is not buildable due to wetland constraints. Great location with easy build. There is no engineering available. Survey is old and not accurate. Very little infrastructure needed. See brochure in documents. Additional Information: SoilType:Unknown,

    Joe Distelburger Keller Williams Realty

    2 Virginia Ln, Goshen, NY 10924
  • /2

    $500,000

    • Land
    • 0.83 Acre
    • $603,355 per Acre

    0 Main St, Chester, NY 10918

    Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • /2

    $299,900

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

    2104 Whispering Hills, Chester, NY 10918

    WHISPERING HILLS!! SOLD AS IS!!! Largest Model! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Living Room! Master Bedroom Suite with Walk in Closet! Patio! Country Club Living! Clubhouses! Pools! Tennis! Basket Ball! Tot Lot! Dog Walk! Perfect Commuter Location! Walk to NY Bus! Close to Major Highway & Shopping!

    Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
How to Buy a Home How to Finance a Home How to Sell a Home