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Newest Homes for Sale in Chester, NY

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  • 3409 Whispering Hills, Chester, NY 10918
    3409 Whispering Hills, Chester, NY 10918
    /2

    $360,000

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

    3409 Whispering Hills, Chester, NY 10918

    Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways.Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace,

    Bernadette Giordano Howard Hanna Rand Realty

    3409 Whispering Hills, Chester, NY 10918
  • 188 Creamery Pond Rd, Chester, NY 10918
    188 Creamery Pond Rd, Chester, NY 10918
    188 Creamery Pond Rd, Chester, NY 10918
    /46

    $675,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 3,202 Sq Ft

    188 Creamery Pond Rd, Chester, NY 10918

    The search for your DREAM HOME ends when you visit this property, since it will check all your boxes ! LOCATION which is perfect for commuters, just a few feet away from the charming Sugar Loaf Craft Village, situated between Warwick and Chester for your enjoyment and convenience of both town's amenities and activities. Corner lot, vinyl siding, deck overlooking the private backyard with a raised

    Patricia Brady Keller Williams Realty

    188 Creamery Pond Rd, Chester, NY 10918
  • 2124 Whispering Hills, Chester, NY 10918
    2124 Whispering Hills, Chester, NY 10918
    2124 Whispering Hills, Chester, NY 10918
    /18

    $299,000

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

    2124 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes, highways, and bus service to NYC, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to

    Beverly Huaman Howard Hanna Rand Realty

    2124 Whispering Hills, Chester, NY 10918
  • 3561 State Route 94, Chester, NY 10918
    3561 State Route 94, Chester, NY 10918
    /2

    $649,999

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 2,902 Sq Ft

    3561 State Route 94, Chester, NY 10918

    Showings begin on 8/28. More information and pics coming soon.

    Gina Dudgeon Howard Hanna Rand Realty

    3561 State Route 94, Chester, NY 10918
  • 72 Lake Region Blvd, Monroe, NY 10950
    72 Lake Region Blvd, Monroe, NY 10950
    72 Lake Region Blvd, Monroe, NY 10950
    /10

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,854 Sq Ft

    72 Lake Region Blvd, Monroe, NY 10950

    Opportunity knocks in Walton Park. 72 Lake Region Blvd is a 3-bedroom, 2 bath home offering 1,854 square feet on a 9,690 square foot lot, and it has the one thing you cannot renovate into a house: excellent bones. Hardwood floors, a solid structure, a 2-car garage, and a layout worth restoring. The home needs renovation including a new roof, and it is priced accordingly at 499,000. Oil heat and a

    Peter Sisca Real Broker NY LLC

    72 Lake Region Blvd, Monroe, NY 10950
  • 255 Heritage Ln, Monroe, NY 10950
    255 Heritage Ln, Monroe, NY 10950
    255 Heritage Ln, Monroe, NY 10950
    /33

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft

    255 Heritage Ln, Monroe, NY 10950

    Welcome to Windridge! This well-maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfortable, carefree living in a convenient Hudson Valley location. The first floor features a spacious eat-in kitchen with new stainless-steel appliances, a powder room, and an open living/dining area with sliding doors leading to the patio. Upstairs offers two bedrooms, a full bath, and a spacious

    Agent Photo

    Elsa Seguinot

    Coldwell Banker Realty

    255 Heritage Ln, Monroe, NY 10950
  • 13 Bianca Blvd, Chester, NY 10918
    13 Bianca Blvd, Chester, NY 10918
    13 Bianca Blvd, 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
  • 173 Creamery Pond Rd, Chester, NY 10918
    173 Creamery Pond Rd, Chester, NY 10918
    173 Creamery Pond Rd, Chester, NY 10918
    /48

    $699,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 2,533 Sq Ft

    173 Creamery Pond Rd, Chester, NY 10918

    Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities.

    Michele Tobin Keller Williams Realty

    173 Creamery Pond Rd, Chester, NY 10918
  • 65 Oxford Springs Rd, Chester, NY 10918
    65 Oxford Springs Rd, Chester, NY 10918
    65 Oxford Springs Rd, Chester, NY 10918
    /38

    $699,000

    • 5 Beds
    • 3.5 Baths
    • 3,463 Sq Ft

    65 Oxford Springs Rd, Chester, NY 10918

    Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace

    Stephanie Dolan HomeSmart Homes & Estates

    65 Oxford Springs Rd, Chester, NY 10918
  • 1 Sanford Ave, Chester, NY 10918
    1 Sanford Ave, Chester, NY 10918
    1 Sanford Ave, Chester, NY 10918
    /30

    $750,000

    • 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
  • 4827 New York 8, Chester, NY 12817
    4827 New York 8, Chester, NY 12817
    4827 New York 8, Chester, NY 12817
    /41

    $380,000

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft

    4827 New York 8, Chester, NY 12817

    The perfect cottage for your Adirondack getaway or year-round living. Like new , move in condition. Features a cozy living room with electric fireplace, eat in kitchen w/ solid surface countertops & sliding doors opening to back deck, overlooking the large private backyard, Enjoy the evenings by the firepit. Radiant heated floors,. Full bath downstairs. Upstairs features a spacious primary

    Vickie Reed Hunt ERA

    4827 New York 8, Chester, NY 12817
  • 63 Hubshop Rd, Chester, NY 10918
    63 Hubshop Rd, Chester, NY 10918
    63 Hubshop Rd, Chester, NY 10918
    /19

    $459,000

    • 4 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    63 Hubshop Rd, Chester, NY 10918

    Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a

    Ryan Barrett Keller Williams Realty

    63 Hubshop Rd, Chester, NY 10918
  • 34 Boville Ct, Chester, NY 10918
    34 Boville Ct, Chester, NY 10918
    34 Boville Ct, 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
  • 74 Heaton Rd, Monroe, NY 10950
    74 Heaton Rd, Monroe, NY 10950
    74 Heaton Rd, Monroe, NY 10950
    /23

    $530,000

    $529K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,676 Sq Ft

    74 Heaton Rd, Monroe, NY 10950

    Step inside to hardwood floors and a welcoming eat-in kitchen featuring stainless steel appliances, ceramic tile flooring and soft-close cabinetry and drawers. Both full bathrooms have been beautifully updated with newer showers, tile and fixtures, plus the everyday luxury of HEATED FLOORS.The major improvements are already done: 200-amp electrical service (2025), rear property-line fencing

    Barbara Bloch Coldwell Banker Realty

    74 Heaton Rd, Monroe, NY 10950
  • 32 Surrey Rd, Chester, NY 10918
    32 Surrey Rd, Chester, NY 10918
    32 Surrey Rd, Chester, NY 10918
    /39

    $489,000

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

    32 Surrey Rd, Chester, NY 10918

    Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors.

    Agent Photo

    Ammar Iqbal

    eXp Realty

    32 Surrey Rd, Chester, NY 10918
  • 1 Bell Way, Chester, NY 10918
    1 Bell Way, Chester, NY 10918
    1 Bell Way, Chester, NY 10918
    /50

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft

    1 Bell Way, Chester, NY 10918

    COLOR AT THE CURB. A POP OF PERSONALITY AT THE DOOR. FROM THE FIRST HELLO, THIS ONE FEELS LIKE HOME.Before you even step inside, this home makes a memorable first impression. The perennial garden, natural stone walkway, and inviting front door adds just the right pop of color and personality, setting the tone for a home that feels fresh, welcoming and anything but cookie-cutter. Tucked away

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    1 Bell Way, Chester, NY 10918
  • 20 Mountainside Dr, Chester, NY 10918
    20 Mountainside Dr, Chester, NY 10918
    20 Mountainside Dr, 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

    Agent Photo

    Randolph Rogers

    eXp Realty

    20 Mountainside Dr, Chester, NY 10918
  • 1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    /16

    $440,000

    • 3 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    1367 Kings Hwy, Chester, NY 10918

    Historic Colonial Era Home in the Heart of Sugar Loaf, NY. Located just 60 minutes from NYC. Zoned Residential/Commercial. Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Built in 1770, this unique property features:• One of a kind Colonial era home,

    Derek Greene Greene Realty Group

    1367 Kings Hwy, Chester, NY 10918
  • 3 Garnett Hill Rd, Chester, NY 10918
    3 Garnett Hill Rd, Chester, NY 10918
    3 Garnett Hill Rd, Chester, NY 10918
    /50

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    3 Garnett Hill Rd, Chester, NY 10918

    This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the

    Jacob Fried Keller Williams Realty

    3 Garnett Hill Rd, Chester, NY 10918
  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /46

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • 166 Bull Mill Rd, Chester, NY 10918
    166 Bull Mill Rd, Chester, NY 10918
    166 Bull Mill Rd, Chester, NY 10918
    /37

    $340,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    166 Bull Mill Rd, Chester, NY 10918

    Step into the timeless charm of this historic 1800s farmhouse, where character and history come together in a warm, inviting setting. Original details, classic craftsmanship, and the unique character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that

    Stephen Ramundo Keller Williams Valley Realty

    166 Bull Mill Rd, Chester, NY 10918
  • 412 Laroe Rd, Chester, NY 10918
    412 Laroe Rd, Chester, NY 10918
    412 Laroe Rd, Chester, NY 10918
    /46

    $615,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    412 Laroe Rd, Chester, NY 10918

    Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The

    Nathalie Sessoms Howard Hanna Rand Realty

    412 Laroe Rd, Chester, NY 10918
  • 21 Trotting Dr, Chester, NY 10918
    21 Trotting Dr, Chester, NY 10918
    21 Trotting Dr, Chester, NY 10918
    /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
  • 213 Eagleton Dr, Monroe, NY 10950
    213 Eagleton Dr, Monroe, NY 10950
    213 Eagleton Dr, Monroe, NY 10950
    /32

    $389,900

    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    213 Eagleton Dr, Monroe, NY 10950

    Some homes simply make everyday life easier, and 213 Eagleton Drive is one of them. This 3-bedroom, 2.5-bath townhome offers a practical layout with comfortable living spaces, an attached garage, additional driveway parking, and an unfinished basement for lots of storage. During the winter months, the home offers views of the community lake, adding a peaceful backdrop to the changing

    Deborah Warner Keller Williams Valley Realty

    213 Eagleton Dr, Monroe, NY 10950
  • 0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
    /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
  • L4/5 Marina Rd, Chester, NY 12817
    L4/5 Marina Rd, Chester, NY 12817
    L4/5 Marina Rd, Chester, NY 12817
    /6

    $88,900

    • Land
    • 1.79 Acres
    • $49,665 per Acre

    L4/5 Marina Rd, Chester, NY 12817

    This lot has beach rights to two beaches shown on map. Home Owners's associationfee includes beach maintenance only. HOA board is working toward the possibility of installing a boat docking system for the future. Presently there is space of non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's trust of which he is a co-executor. New excavation

    John Palermo Palermo John R

    L4/5 Marina Rd, Chester, NY 12817
  • 102 Hillcrest Ave, Monroe, NY 10950
    102 Hillcrest Ave, Monroe, NY 10950
    102 Hillcrest Ave, Monroe, NY 10950
    /4

    $300,000

    • 2 Beds
    • 1 Bath
    • 1,396 Sq Ft

    102 Hillcrest Ave, Monroe, NY 10950

    Situated in a quiet neighborhood on level corner property. House is in need of complete renovation. A suitable project for experienced contractor/builder.

    Rosy Wansor Wansor Realty

    102 Hillcrest Ave, Monroe, NY 10950
  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, 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
  • 176 Beverly Rd, Chester, NY 10918
    176 Beverly Rd, Chester, NY 10918
    176 Beverly Rd, Chester, NY 10918
    /39

    $699,900

    $77K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    176 Beverly Rd, Chester, NY 10918

    Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid driveway address, professionally landscaped grounds accented by natural stone and in-ground lighting, and an insulated two-car carriage-style garage with glass doors. A grand two-story foyer with soaring ceilings, elegant wainscoting, and abundant

    David White Owner Entry.com

    176 Beverly Rd, Chester, NY 10918
  • L20 Granite Ridge Rd, Chester, NY 12817
    L20 Granite Ridge Rd, Chester, NY 12817
    /2

    $39,000

    • Land
    • 1.32 Acres
    • $29,545 per Acre

    L20 Granite Ridge Rd, Chester, NY 12817

    Beautiful 1.32 acre parcel in Adirondack Heights! APA approved Subdivision of Adirondack Heights with proposed home location that is already cleared with underground power! Close proximity to all your local lakes, hiking trails, Gore Mountain & Chestertown. Your Adirondack adventure awaits!

    Nancy Freebern Gallo Realty ADK Inc

    L20 Granite Ridge Rd, Chester, NY 12817
  • 66 Whitetail Run, Chester, NY 10918
    66 Whitetail Run, Chester, NY 10918
    66 Whitetail Run, Chester, NY 10918
    /50

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    66 Whitetail Run, Chester, NY 10918

    Welcome to 66 Whitetail Run – Chester, NY.Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities.Step inside to a

    Soleil Jackman Howard Hanna Rand Realty

    66 Whitetail Run, Chester, NY 10918
  • 2522 Whispering Hills Unit 518, Chester, NY 10918
    2522 Whispering Hills Unit 518, Chester, NY 10918
    2522 Whispering Hills Unit 518, 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
  • 23 Pike Ct, Monroe, NY 10950
    23 Pike Ct, Monroe, NY 10950
    23 Pike Ct, Monroe, NY 10950
    /8

    $425,000

    • 3 Beds
    • 2 Baths
    • 2,460 Sq Ft

    23 Pike Ct, Monroe, NY 10950

    Welcome to 23 Pike Court. Unlock the potential of this spacious 3-bedroom, 2-bath raised ranch, which offers 2,460 square feet of living space on a generous .75 acre lot, giving you the space and flexibility to create something truly special. Perfect for an investor, contractor, or DIY enthusiast, this home is ready for someone with vision. While it needs work, it is move-in ready and offers an

    Patricia Sassi RE/MAX Benchmark Realty Group

    23 Pike Ct, Monroe, NY 10950
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow 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
  • 3 Hilltop Ln, Chester, NY 10918
    3 Hilltop Ln, 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
  • 151 Main St, Chester, NY 10918
    151 Main St, Chester, NY 10918
    151 Main St, 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
  • 4008 Whispering Hills Dr, Chester, NY 10918
    4008 Whispering Hills Dr, Chester, NY 10918
    4008 Whispering Hills Dr, Chester, NY 10918
    /33

    $290,000

    $25K PRICE DROP
    • 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
  • 68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    68 Conklingtown Rd Unit 1&2, 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
  • 1 Hilltop Ln, Chester, NY 10918
    1 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
  • 29 Murray Dr, Chester, NY 10918
    29 Murray Dr, Chester, NY 10918
    29 Murray Dr, Chester, NY 10918
    /34

    $650,000

    • 3 Beds
    • 4 Baths
    • 2,520 Sq Ft

    29 Murray Dr, Chester, NY 10918

    Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances

    Liudmila Lobeeva eXp Realty

    29 Murray Dr, Chester, NY 10918

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Newest Listings for Sale in Chester, NY

Frequently Asked Questions

What is the average home price in Chester, NY?
Homes for sale in Chester, NY have an average home price of $635,042.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Chester, NY?
84 homes have sold in Chester, NY over the last 12 months.
What is the average household income in Chester, NY?
The average household income in Chester, NY is $137K.
What are the most popular zip codes in Chester, NY?
The most popular zip codes in Chester, NY include 10918, 10950, 10990, 10924 and 10921.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $605,000. If you put a 20% down payment of $121,000 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $3,110 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $133K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $137K.
How are the schools in Chester, NY?
Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Greenwood Lake Elementary School, Warwick Valley High School and CJ Hooker Middle School. Browse all the schools in Chester, NY to learn more.

Home Prices in Chester, NY

The median home sale price in Chester, NY is $500,750, down 5% year-over-year. Homes in Chester sell in 66 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$500,750
Median Single Family Sale Price
$669,000
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
69
Last 12 months Home Sales
84
Months of Supply
9.90
Median List Price
$605,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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