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Newest Homes for Sale in Chester, NY

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  • 360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    /50

    $699,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    360 Prospect Rd, Chester, NY 10918

    B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

    Joseph Mendlowitz eRealty Advisors, Inc

    360 Prospect Rd, Chester, NY 10918
  • 6 Vista Dr, Chester, NY 10918
    6 Vista Dr, Chester, NY 10918
    6 Vista Dr, Chester, NY 10918
    /45

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,934 Sq Ft

    6 Vista Dr, Chester, NY 10918

    Stunning Chester Home with Pool, Pond & Private Backyard Oasis! Discover your own private retreat in this meticulously maintained 3-bedroom, 2.5-bath home in Chester. Perfectly positioned for privacy on a scenic lot featuring its own backyard pond, this property offers a rare combination of comfort and outdoor amenities. Step inside to a bright and airy main level where hardwood floors connect

    Christine Koenig Keller Williams Realty

    6 Vista Dr, Chester, NY 10918
  • 4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    /40

    $849,000

    • 5 Beds
    • 5.5 Baths
    • 5,403 Sq Ft

    4 Debbie Ct, Chester, NY 10918

    DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

    Joseph Rosenfeld Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
  • 3120 Whispering Hills, Chester, NY 10918
    3120 Whispering Hills, Chester, NY 10918
    3120 Whispering Hills, Chester, NY 10918
    /18

    $310,000

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

    3120 Whispering Hills, Chester, NY 10918

    Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a

    Bente Brown John J Lease REALTORS Inc

    3120 Whispering Hills, Chester, NY 10918
  • 3917 Whispering Hills, Chester, NY 10918
    3917 Whispering Hills, Chester, NY 10918
    3917 Whispering Hills, Chester, NY 10918
    /28

    $319,000

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

    3917 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

    Jie Liu Keller Williams Hudson Valley

    3917 Whispering Hills, Chester, NY 10918
  • 101 Oxford Rd, Chester, NY 10918
    101 Oxford Rd, Chester, NY 10918
    /2

    $669,000

    • 3 Beds
    • 1.5 Baths
    • 1,816 Sq Ft

    101 Oxford Rd, Chester, NY 10918

    This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

    Nathan Landau Loop Realty Inc

    101 Oxford Rd, Chester, NY 10918
  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /11

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Two story center unit with full basement located in Windridge community. Primary bedroom has large sitting area which can be used as home office. Sliders to rear patio with lake views!! Large living and dining area. Beautiful complex with mountain views.

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, Chester, NY 10918
  • 4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    /48

    $1,050,000

    • 5 Beds
    • 4 Baths
    • 5,080 Sq Ft

    4 Camelback Rd, Chester, NY 10918

    The one you don't to miss. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This meticulously

    Alexander Fayn Prominent Properties Sotheby's

    4 Camelback 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
    /50

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 3,617 Sq Ft

    65 Oxford Springs Rd, Chester, NY 10918

    Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on a private, 2.3-acre hilltop. This property offers the perfect mix of privacy, space, and convenience, all just minutes from the NYS Thruway, local state parks, and about 50 minutes from NYC. Inside, the home features a bright, open floor plan with plenty of natural light. You’ll find rich hardwood floors,

    Ammar Iqbal eXp Realty

    65 Oxford Springs Rd, Chester, NY 10918
  • 16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    /48

    $750,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft

    16 Oxford Springs Rd, Chester, NY 10918

    Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

    Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
  • 1503 Whispering Hills, Chester, NY 10918
    1503 Whispering Hills, Chester, NY 10918
    1503 Whispering Hills, Chester, NY 10918
    /17

    $309,900

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

    1503 Whispering Hills, Chester, NY 10918

    Big price reduction! Come see it before it's gone. 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

    Darlene Provino Century 21 E & M Williams Rlty

    1503 Whispering Hills, Chester, NY 10918
  • L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    /5

    $35,000

    • Land
    • 7.07 Acres
    • $4,950 per Acre

    L30 Lane Rd, Chester, NY 12853

    You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

    Julia Pucciarelli Gallo Realty ADK Inc

    L30 Lane Rd, Chester, NY 12853
  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 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
  • 36 Marian Ct, Warwick, NY 10990
    36 Marian Ct, Warwick, NY 10990
    36 Marian Ct, Warwick, NY 10990
    /27

    $395,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    36 Marian Ct, Warwick, NY 10990

    Turnkey Townhome with Scenic Views – No HOA – Warwick School District. Welcome to your newly renovated 2-bedroom, 1.5-bath townhome in the heart of Warwick, just 60 minutes from NYC. This beautifully updated home is perfect for first-time buyers or anyone seeking a stylish, low-maintenance lifestyle in a quiet, commuter-friendly setting—without the restrictions of an HOA. Set against a backdrop

    Courtney Tablante Keller Williams Realty

    36 Marian Ct, Warwick, NY 10990
  • 65 Hudson St, Chester, NY 10918
    65 Hudson St, Chester, NY 10918
    65 Hudson St, 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
  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /31

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

    Debbie Walsh SHAHAR Management LLC

    2 Pine Hill Rd, Chester, NY 10918
  • 651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    /7

    $874,900

    • 4 Beds
    • 2 Baths
    • 2,466 Sq Ft

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • 15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    /5

    $54,900

    • Land
    • 10.14 Acres
    • $5,414 per Acre

    15 Deer Run, Chester, NY 12817

    10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

    Patricia Seitz McAlonen Pearsall Realty

    15 Deer Run, Chester, NY 12817
  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /50

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    220 Oxford Rd, Chester, NY 10918

    Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres of peaceful living. Featuring 4 spacious bedrooms and 3.5 bathrooms, this home has been beautifully renovated with new plumbing, spotlights, flooring, kitchen, painting, and full wiring for a camera and security system. Enjoy a large eat-in kitchen, formal dining room, cozy family room, and a bright attic

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • 23 W Meadow Way, Warwick, NY 10990
    23 W Meadow Way, Warwick, NY 10990
    23 W Meadow Way, Warwick, NY 10990
    /48

    $920,000

    • 4 Beds
    • 2.5 Baths
    • 2,969 Sq Ft

    23 W Meadow Way, Warwick, NY 10990

    Views abound from this stunning colonial in the Warwick Ridge Sub-Division. Don't miss out on this custom built colonial.includes Chefs kitchen, quartz counters, extensive trim package, custom tile, hardwood the worksAccepted Offer 12/1

    Robert Valentine BHG Real Estate Green Team

    23 W Meadow Way, Warwick, NY 10990
  • 16 Mari Rd, Chester, NY 10918
    16 Mari Rd, Chester, NY 10918
    16 Mari Rd, Chester, NY 10918
    /38

    $500,000

    • 4 Beds
    • 3 Baths
    • 2,098 Sq Ft

    16 Mari Rd, Chester, NY 10918

    Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor.

    Kimberly Corkum Keller Williams Realty

    16 Mari Rd, Chester, NY 10918
  • 7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    /48

    $740,000

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft

    7 Park Place, Chester, NY 10918

    Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

    Luanne McGann Century 21 Full Service Realty

    7 Park Place, Chester, NY 10918
  • L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    /31

    $65,000

    • Land
    • 5.42 Acres
    • $11,993 per Acre

    L7 Macglashan Ln, Chester, NY 12817

    Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

    Walter Swartz Gallo Realty ADK Inc

    L7 Macglashan Ln, Chester, NY 12817
  • 9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    /30

    $725,000

    • 5 Beds
    • 2.5 Baths
    • 3,124 Sq Ft

    9 Country Woods Dr, Chester, NY 10918

    Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

    Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
  • 69 Cedar Pond Ln, Chester, NY 10918
    69 Cedar Pond Ln, Chester, NY 10918
    69 Cedar Pond Ln, Chester, NY 10918
    /93

    $1,875,000

    • 6 Beds
    • 7.5 Baths
    • 7,034 Sq Ft

    69 Cedar Pond Ln, Chester, NY 10918

    Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the

    Emily Iason Four Seasons Sotheby's Int.

    69 Cedar Pond Ln, Chester, NY 10918
  • L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    /14

    $144,900

    • Land
    • 0.47 Acre
    • $308,298 per Acre

    L31 Clarkson Rd, Chester, NY 12817

    Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

    Brooke Clark Four Seasons Sotheby's International Realty

    L31 Clarkson Rd, Chester, NY 12817
  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    /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
  • 5 Berkley Terrace, Monroe, NY 10950
    5 Berkley Terrace, Monroe, NY 10950
    5 Berkley Terrace, Monroe, NY 10950
    /24

    $530,000

    • 4 Beds
    • 2 Baths
    • 1,322 Sq Ft

    5 Berkley Terrace, Monroe, NY 10950

    Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

    Layla Rose Boyles Century 21 Realty Center

    5 Berkley Terrace, Monroe, NY 10950
  • 8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    /11

    $349,999

    • Land
    • 4.9 Acres
    • $71,428 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

    James Feldhaus eXp Realty

    8 Camelback Rd, Chester, NY 10918
  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /23

    $430,000

    • 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
  • 32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    /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
  • 34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, 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
  • 391 Bull Mill Rd, Chester, NY 10918
    391 Bull Mill Rd, Chester, NY 10918
    391 Bull Mill Rd, Chester, NY 10918
    /32

    $509,999

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    391 Bull Mill Rd, Chester, NY 10918

    Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 412-9860

    391 Bull Mill Rd, Chester, NY 10918
  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /48

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,467 Sq Ft

    53 Odyssey Dr, Chester, NY 10918

    Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

    Hilary Ryan Goldman Howard Hanna Rand Realty

    53 Odyssey Dr, Chester, NY 10918
  • 78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    /37

    $569,999

    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    78 Pickerel Rd, Monroe, NY 10950

    Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

    Lauren Kelly Howard Hanna Rand Realty

    78 Pickerel Rd, Monroe, NY 10950
  • 37 Main St, Chester, NY 10918
    37 Main St, Chester, NY 10918
    37 Main St, 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
  • 0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    /4

    $350,000

    • Land
    • 5.1 Acres
    • $68,627 per Acre

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

    Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

    Theresa Powers Keller Williams Realty

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

Showing Results 1 - 40, Page 1 of 2

New York Orange County Chester

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 $613,024.
How many homes have sold over the last 12 months in Chester, NY?
106 homes have sold in Chester, NY over the last 12 months.
What are the most popular zip codes in Chester, NY?
The most popular zip codes in Chester, NY include 10918, 10990, 10950, 10924 and 10921.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $554,000. If you put a 20% down payment of $110,800 and had a 30-year fixed mortgage with an interest rate of 6.15%, your estimated principal and interest payment would be $2,700 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
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 Warwick Valley Middle School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 60 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, NY over the last 12 months is $510,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$510,000
Median Single Family Sale Price
$614,750
Median Townhouse Sale Price
$322,500
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$265
Number of Homes for Sale
25
Last 12 months Home Sales
106
Months of Supply
2.80
Median List Price
$554,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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