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Homes for Sale in 10918

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  • /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
  • /28

    $515,000

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

    25 High St, Chester, NY 10918

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

    Agent Photo

    Alicia Goldman

    Christie's Int. Real Estate

    (845) 244-4823

    25 High St, Chester, NY 10918
  • /30

    $660,000

    • 3 Beds
    • 2 Baths
    • 1,987 Sq Ft

    39 Peddler Hill Rd, Monroe, NY 10950

    Welcome to your dream home in the heart of Monroe, NY—where modern elegance meets everyday convenience. This beautifully appointed 1,987 sq ft raised ranch offers a perfect blend of contemporary design, generous living space, and a prime location just one hour from New York City. With 3 spacious bedrooms, 2 updated bathrooms, and a layout crafted for both comfort and style, this home is ready to

    Jessica Evans Keller Williams Hudson Valley

    39 Peddler Hill Rd, Monroe, NY 10950
  • /93

    $1,975,000

    • 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

    Emily Iason Four Seasons Sotheby's Int.

    69 Cedar Pond Ln, 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
  • /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
  • /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
  • /2

    $499,000

    • Land
    • 4.5 Acres
    • $110,889 per Acre

    1414 Kings Hwy, Chester, NY 10918

    5 Lot subdivision which has been engineered and submitted to Chester planning board for approvals with water and sewer. Not approved but in the process. Buyer must finish. Site plan in documents as well as addressed planning board comments. Additional Information: SoilType:Unknown,

    Joe Distelburger Keller Williams Realty

    1414 Kings Hwy, Chester, NY 10918
  • /5

    $259,000

    • Land
    • 20.18 Acres
    • $12,834 per Acre

    32 Mountainside Dr, Chester, NY 10918

    A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • /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
  • /19

    $900,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    32 Fox Hollow Dr, Blooming Grove, NY 10918

    Discover a one-of-a-kind opportunity to own a modern ranch home on almost 6 acres that combines the tranquility of a scenic rural setting with the clean lines and comforts of contemporary living. Boasting over 3,500 finished sq. ft., this thoughtfully designed home offers 5 spacious bedrooms, including a private guest quarters located above the oversized 2-car garage, perfect for hosting

    Julissa Amaro Keller Williams Hudson Valley

    32 Fox Hollow Dr, Blooming Grove, NY 10918
  • /4

    $350,000

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

    2 Virginia Ln, Goshen, NY 10924

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

    Joe Distelburger Keller Williams Realty

    2 Virginia Ln, Goshen, NY 10924
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /2

    $164,400

    • Land
    • 14.4 Acres
    • $11,417 per Acre

    0 Route 94 Unit 11617205, Blooming Grove, NY 10950

    Online Only Auction Ending January 8 at AARauctions View website for complete details and photos. New Year - New Opportunity Real Estate Auction. COMMERCIAL LAND 14.40+/-acres ready for your money-making development vision along busy NYS Route 94. What will you design? How will you maximize this parcel's potential? Inquiring minds want to know. Act fast and dream big. There will only be one

    Frank Pietrzak ABSOLUTE AUCTION AND REALTY INC

    0 Route 94 Unit 11617205, Blooming Grove, NY 10950
  • /2

    $500,000

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

    0 Main St, Chester, NY 10918

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

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • /2

    $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
  • /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
  • /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
  • /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
  • /23

    $325,000

    • Land
    • 5.4 Acres
    • $60,185 per Acre

    0 Oxford Rd Unit ONEH6287716, Blooming Grove, NY 10918

    BUILD YOUR DREAM HOME !!! 5.4 acre lot in country setting, with 2000sf garage. Outbuilding/garage has a 12' garage door;14' ceilings. Perfect for storage. Partially wooded with walking paths and a spring fed pond. Located in the desirable town of Chester, within the Monroe- Woodbury School District, you'll enjoy a peaceful and private setting while still being convienently close to

    Donna Brunell RE/MAX Benchmark Realty Group

    0 Oxford Rd Unit ONEH6287716, Blooming Grove, 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
  • /49

    $1,500,000

    206 Greycourt Rd Unit 190, Chester, NY 10918

    **Endless Opportunities Await on This Rare 3.2-Acre Property!** ZONED COMMMERCIAL INDUSTRIAL USEFor the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home.

    Susan McMullen eXp Realty

    206 Greycourt Rd Unit 190, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /49

    $734,000

    • 4 Beds
    • 2.5 Baths
    • 3,112 Sq Ft

    15 Old Dominion Rd, Blooming Grove, NY 10914

    With over 3,000 sq ft of living space and set on 7.5 open, level acres, this sun-filled Colonial delivers unbeatable value, inside and out. From the moment you arrive, you're greeted by wide-open skies, sweeping lawn, and views that stretch as far as the eye can see. This home has been lovingly maintained by caring owners and offers a thoughtful layout ideal for both everyday living and

    Lazar Schvimmer Blooming Realty

    15 Old Dominion Rd, Blooming Grove, NY 10914
  • /48

    $750,000

    • 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
  • /15

    $999,000

    • 3 Beds
    • 1 Bath
    • 1,148 Sq Ft

    168 Prospect Rd, Monroe, NY 10950

    Welcome to your dream home! Lovingly maintained and nestled in a peaceful community, this charming ranch sits on a picturesque one-acre lot.Step inside to a warm and inviting living space, highlighted by a cozy wood-burning stove—perfect for chilly evenings. The home features three comfortable bedrooms and a well-appointed bathroom, offering both comfort and functionality.Enjoy

    Salvatore Girgenti Ben Bay Realty of Staten Isl.

    168 Prospect Rd, Monroe, NY 10950
  • /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
  • /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
  • /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

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