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Homes for Sale near Chester Elementary School

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  • /37

    $789,900

    • 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
  • /35

    $374,999

    $25K PRICE DROP Pre-Foreclosure
    • 4 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    241 Meadow Ave, Chester, NY 10918

    Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

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    Chativa Bowen

    Keller Williams Realty

    241 Meadow Ave, Chester, NY 10918
  • /50

    $990,000

    $10K PRICE DROP
    • 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
  • /36

    $540,000

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

    5 Walnut Ct, Goshen, NY 10924

    Lovely raised ranch on a cul de sac. Updated kitchen and bathrooms. Open floor plan with a deck off the kitchen/dining area. The deck is fabulous and large, perfect for entertaining, dining al fresco, enjoying a beverage of your choice or lounging with a good read. Beautiful, large backyard. Don't miss the opportunity to own a home that gives you a lot for your money. Come explore the lay out see

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    Pamela Burns

    Corcoran Legends Realty

    5 Walnut Ct, Goshen, NY 10924
  • /33

    $315,000

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

    4008 Whispering Hills Dr, Chester, NY 10918

    Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for

    Karen Taphorn Howard Hanna Rand Realty

    4008 Whispering Hills Dr, Chester, NY 10918
  • /36

    $375,000

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

    1310 Whispering Hills, Chester, NY 10918

    Welcome to this comfortable 3-bedroom, 3-bathroom, end unit condo with a 2-car garage in the Whispering Hills community of Chester, NY. It’s the kind of place that feels easy the moment you walk in—spacious enough for everyday living, yet low-maintenance so you can actually enjoy your free time.Whispering Hills is one of those communities that just works. Residents get access to two outdoor

    Joseph Williams Hudson Premium Realty

    1310 Whispering Hills, Chester, NY 10918
  • /48

    $450,000

    $50K 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
  • /37

    $749,000

    • 6 Beds
    • 3 Baths
    • 3,066 Sq Ft

    3 Grand View Terrace, Chester, NY 10918

    Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

    Shalom Landau eRealty Advisors, Inc

    3 Grand View Terrace, Chester, NY 10918
  • /24

    $295,000

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

    2113 Whispering Hills Unit 178, Chester, NY 10918

    Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

    Valerie Quinn Keller Williams Realty

    2113 Whispering Hills Unit 178, Chester, NY 10918
  • /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    3 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    3 Hilltop Ln, Chester, NY 10918
  • /35

    $629,000

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

    14 Larchwood Dr, Goshen, NY 10924

    Gorgeous corner fully fenced in Bi-Level house for sale in Town of Goshen. State of the art heating system, central air, beautiful sunroom, modern kitchen and bathrooms. House was fully remodeled in 2014. The main level features three bedrooms, master bathroom has walk in closet with access to the bathroom, spacious living room, dinning room, kitchen and sunroom. The lower level offers additional

    Jonathan Minerick HomeCoin.com

    14 Larchwood Dr, Goshen, NY 10924
  • /29

    $389,900

    • 3 Beds
    • 2 Baths
    • 1,393 Sq Ft

    4114 Whispering Hills, Chester, NY 10918

    WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door)

    Gzim Hakanjin Coldwell Banker Realty

    4114 Whispering Hills, 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 One of America's Great Equestrian LandmarksSteeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of

    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
  • /3

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    2 Boville Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    2 Boville Ct, Chester, NY 10918
  • /49

    $749,999

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is

    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
  • /2

    $1,975,000

    • Land
    • 79.2 Acres
    • $24,937 per Acre

    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914

    A once-in-a-generation opportunity to acquire 79.2 acres in the highly sought-after Town of Blooming Grove. Rarely does a parcel of this size become available in one of Orange County's fastest-growing and most desirable communities. Whether you're a long-term investor, developer, or land banker, this exceptional property offers tremendous upside and the potential to capitalize on the area's

    Yoel Kornbluh Mount Realty

    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
  • /35

    $377,000

    $20K PRICE DROP
    • 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
  • /34

    $349,999

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

    3414 Whispering Hills, Chester, NY 10918

    Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

    Kevin Grier KW Hudson Valley United

    3414 Whispering Hills, Chester, NY 10918
  • /22

    $550,000

    $25K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,968 Sq Ft

    2 Sycamore Ln, Goshen, NY 10924

    Charming Split Three-Level fenced in property located Hudson Valley's Chester School District in Goshen, New York. Don't miss the opportunity to preview this beautiful home featuring three bedrooms, den, family room, two bathrooms, 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

    Jeanette Santory Howard Hanna Rand Realty

    2 Sycamore Ln, Goshen, NY 10924
  • /50

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    21 Trotting Dr, Chester, NY 10918

    Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend

    Michele Kayser Keller Williams Realty

    21 Trotting Dr, Chester, NY 10918
  • /2

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,677 Sq Ft

    1 Arborvitae Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    1 Arborvitae Ct, Chester, NY 10918
  • /50

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    3 Boville Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Dovid Hoffman MK Realty Inc

    3 Boville Ct, Chester, NY 10918
  • /32

    $295,000

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft

    2119 Whispering Hills, Chester, NY 10918

    Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and

    Jasmine Wadhwa Howard Hanna Rand Realty

    2119 Whispering Hills, 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
  • /28

    $559,000

    $21K PRICE DROP
    • 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
  • /45

    $495,000

    Coming Soon
    • 4 Beds
    • 1.5 Baths
    • 1,820 Sq Ft

    8 Bridle Ln, Chester, NY 10918

    Welcome to 8 Bridle Lane, Chester, NY, located in the desirable Surrey Meadows neighborhood. Lovingly owned by just one family, this well-maintained 4-bedroom, 1.5-bath has been beautifully cared for and is truly move-in ready.Inside, you'll find beautiful hardwood floors, a comfortable floor plan, and tastefully updated kitchen and baths that blend timeless style with everyday functionality.

    John Olivero Keller Williams Realty

    8 Bridle Ln, Chester, NY 10918
  • /16

    $325,000

    $25K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,504 Sq Ft

    151 Main St, Chester, NY 10918

    A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors!

    Eveline White Hudson Valley Griffith

    151 Main St, Chester, NY 10918
  • /13

    $579,900

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,583 Sq Ft

    50 Hambletonian Ave, Chester, NY 10918

    4 ACRES | RENOVATED | VILLAGE OF CHESTER | PRIVATE & MOVE-IN READY. FOR SALE BY OWNER. Rarely do you find 4 private acres in the heart of the Village of Chester. Welcome to 50 Hambletonian Avenue, a beautifully renovated home offering the perfect combination of privacy, space, and convenience. Just steps from Chester Academy and the Heritage Trail, you’re close to schools, shops, restaurants,

    Derek Greene Greene Realty Group

    50 Hambletonian Ave, Chester, NY 10918
  • /26

    $379,900

    $45K 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
  • /21

    $370,000

    • 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
  • /5

    $850,000

    • 5 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    5 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail

    Moshe Kaufman MK Realty Inc

    5 Hilltop Ln, Chester, NY 10918
  • /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    1 Hilltop Ln, Chester, NY 10918
  • /2

    $1,700,000

    • Land
    • 46.5 Acres
    • $36,559 per Acre

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

    Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

    Lazar Schvimmer Mount Realty

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
  • /44

    $279,999

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft

    2007 Whispering Hills, Chester, NY 10918

    Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two

    Philip Szumlaski Keller Williams Realty

    2007 Whispering Hills, Chester, NY 10918
  • /35

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,086 Sq Ft

    2604 Whispering Hills, Chester, NY 10918

    Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and

    Sonia Gonzalez HomeSmart Homes & Estates

    2604 Whispering Hills, Chester, NY 10918
  • /38

    $575,000

    • 6 Beds
    • 2 Baths

    68 Conklingtown Rd Unit 1&2, Chester, NY 10918

    Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The

    Moses Schreiber MS Realty Group USA, Inc

    68 Conklingtown Rd Unit 1&2, Chester, NY 10918
  • /27

    $469,000

    • 3 Beds
    • 3 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate

    Pedro Garcia Curasi Realty, Inc.

    70 Main St, Chester, NY 10918
  • /35

    $369,000

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

    2522 Whispering Hills Unit 518, Chester, NY 10918

    Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're downsizing for care free, low maintenance living. Enjoy this spacious 3 bedroom, 3 bath townhouse with lots of storage and your private garage with direct entry into your home. Comfortable and spacious bedroom layouts with baths and

    Ann Marie Silvani Howard Hanna Rand Realty

    2522 Whispering Hills Unit 518, Chester, NY 10918
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