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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

    Agent Photo

    Randolph Rogers

    eXp Realty

    19 Grand View Terrace, Chester, NY 10918
  • /49

    $700,000

    • 4 Beds
    • 2.5 Baths
    • 3,296 Sq Ft

    13 Bianca Blvd, Chester, NY 10918

    Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,

    Theresa Powers

    Keller Williams Realty

    13 Bianca Blvd, Chester, NY 10918
  • /50

    $549,000

    • 4 Beds
    • 2 Baths
    • 2,824 Sq Ft

    147 Main St, Chester, NY 10918

    Bring your vision to **147 Main Street in the Village of Chester**. Zoned **Duplex with Neighborhood Business use**, this spacious property offers an excellent opportunity for investors, business owners or buyers looking to renovate and create value.The property features multiple living areas, four bedrooms, a large kitchen with center island, one full bathroom, a half bathroom, laundry

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    Samantha Ortiz

    Howard Hanna Rand Realty

    147 Main St, Chester, NY 10918
  • /36

    $749,900

    • 4 Beds
    • 4 Baths
    • 3,080 Sq Ft

    20 Mountainside Dr, Chester, NY 10918

    20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

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    Randolph Rogers

    eXp Realty

    20 Mountainside Dr, Chester, NY 10918
  • /50

    $990,000

    Open Sat 12PM - 2PM $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
  • /45

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,583 Sq Ft

    50 Hambletonian Ave, Chester, NY 10918

    Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an

    Agent Photo

    Jennifer Loprieno

    Howard Hanna Rand Realty

    50 Hambletonian Ave, Chester, NY 10918
  • /36

    $519,000

    $21K PRICE DROP
    • 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

    Agent Photo

    Pamela Burns

    Corcoran Legends Realty

    5 Walnut Ct, Goshen, NY 10924
  • /35

    $349,999

    $50K 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

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    241 Meadow Ave, Chester, NY 10918
  • /32

    $750,000

    Open Sat 2PM - 4PM
    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    1 Sanford Ave, Chester, NY 10918

    Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal.Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious

    Danielle Hinton Redfin Real Estate

    1 Sanford Ave, Chester, NY 10918
  • /24

    $275,000

    $20K PRICE DROP
    • 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
  • /46

    $839,000

    • 4 Beds
    • 4 Baths
    • 2,707 Sq Ft

    34 Boville Ct, Chester, NY 10918

    Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a peaceful cul-de-sac and set on just shy of two acres. Thoughtfully designed with timeless style and modern functionality, this completely move-in-ready home offers an exceptional blend of space, comfort, and sophistication. Step inside to beautiful hardwood floors and a bright, inviting layout made for both

    Jillian Laga Keller Williams Valley Realty

    34 Boville Ct, Chester, NY 10918
  • /48

    $269,000

    Open Sat 12PM - 2PM
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1212 Whispering Hills, Chester, NY 10918

    Welcome to stress-free Hudson Valley living in the desirable Whispering Hills community! This end unit, bright and airy 2-bedroom, 1-bathroom condo features soaring cathedral ceilings, a cozy fireplace, and an updated kitchen complete with sleek stainless steel appliances. Enjoy fantastic turn-key amenities right outside your door, including two community pools, a clubhouse, gym, tennis,

    Beth Palma Keller Williams Realty

    1212 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

    $744,999

    Open Sat 12PM - 2PM $55K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Looking for a spacious home that has everything? Look no more! Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial offers over 3,300sqft of living space! The property offers four spacious sleeping areas (room for 8+) and 2.5 baths. Endless possibilities for additional use continue on the 3rd floor with a 15 x 42 climate-controlled walk-up attic, offering

    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
  • /2

    $329,000

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

    2107 Whispering Hills, Chester, NY 10918

    Welcome to 2107 Whispering Hills, a comfortable 2-bedroom, 1-bath condo offering 1,086 square feet of living space in a convenient Chester location. This home offers an easy, low-maintenance lifestyle with a practical layout and plenty of opportunity to make the space your own.Residents can enjoy community amenities including a swimming pool, providing a great place to relax and enjoy the

    Zachary Leentjes Wansor Realty

    2107 Whispering Hills, Chester, NY 10918
  • /18

    $299,900

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

    1223 Whispering Hills Unit 138, Chester, NY 10918

    PRICED TO SELL! Bright and spacious 3-bedroom, 2-bath end-unit townhouse in Whispering Hills, offered at an attractive price compared with other condos in the community. Enjoy a cozy fireplace, double patio sliders to a private patio and open yard, generous bedrooms, ample storage, and a private garage with direct entry.Whispering Hills offers resort-style amenities, including a pool,

    Jonathon Lee KW Hudson Valley United

    1223 Whispering Hills Unit 138, 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

    Jake Garay Serhant LLC

    19 Greentree Ln, Chester, NY 10918
  • /28

    $525,000

    $55K 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
  • /19

    $370,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    4704 Whispering Hills, Chester, NY 10918

    Welcome home to your beautiful, quiet and peaceful oasis. This 3 bed/3bath unit with a spacious 2-car garage has many new recent updates including new flooring, updated kitchen and bathroom, and an elegant hanging chandelier. Have your morning coffee or evening dinner on your lovely private patio and in the winter enjoy your cozy fireplace. The amenities will give you that vacation resort feel

    Evelyn Martino Sahagian Realty LLC

    4704 Whispering Hills, Chester, NY 10918
  • /18

    $525,000

    Open Sat 12PM - 2:30PM
    • 2 Beds
    • 2 Baths
    • 1,910 Sq Ft

    19 Meadow Ave, Chester, NY 10918

    Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finished basement and finished attic for all your storage needs. Large 2-car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and an

    Delease Jenkins RE/MAX Town & Country

    19 Meadow Ave, Chester, NY 10918
  • /42

    $364,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2921 Whispering Hills, Chester, NY 10918

    WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace! Master Bedroom Suite with Walk In Closet! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Dog Walk! Perfect Commuter Location! Close to Major Highways, Buses & Shopping! Walk to NYC Bus!

    Amanda Dnistrian ARC Realty 1 in Sales

    2921 Whispering Hills, Chester, NY 10918
  • /16

    $299,000

    $51K 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
  • /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
  • /28

    $290,000

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft

    1005 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors.

    Kristie Jacques Century 21 Full Service Realty

    1005 Whispering Hills, 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
  • /50

    $635,999

    Open Sun 11AM - 1PM $14K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,902 Sq Ft

    3561 State Route 94, Chester, NY 10918

    If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space,

    Gina Dudgeon Howard Hanna Rand Realty

    3561 State Route 94, 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

    $359,000

    $10K PRICE DROP
    • 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
  • /18

    $289,000

    Open Sat 12PM - 2PM $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    2124 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This inviting end-unit home overlooks picturesque woodlands, offering a peaceful and private setting while providing a comfortable blend of everyday living and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for those seeking the comfort and tranquility of home without sacrificing accessibility. Come home to a

    Beverly Huaman Howard Hanna Rand Realty

    2124 Whispering Hills, Chester, NY 10918
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