Homes for Sale in 10918

• 

  

  

  /10

  $585,000 Coming Soon

  • 4 Beds
  • 1.5 Baths
  • 2,191 Sq Ft

  165 Round Hill Rd, Washingtonville, NY 10992

  Welcome to 165 Round Hill Road, a beautiful traditional home set on a peaceful acre with mountain views that never get old. From the moment you arrive, you'll feel the care and history that's been poured into this home over the years. Inside, you'll find many original details that add character and warmth, including parquet flooring and stained glass windows flanking the front door. The family

  Victoria Wander Divine Realty NY, LLC

  165 Round Hill Rd, Washingtonville, NY 10992
• 

  

  /2

  $799,999 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  5 Bens Way, Chester, NY 10918

  On Market Monday 2/9/2026

  Anthony Rivas Keller Williams Hudson Valley

  5 Bens Way, 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.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
• 

  

  

  /38

  $635,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  25 Sugarloaf Mountain Rd, Chester, NY 10918

  MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades.From the moment you step inside, you are greeted by a stunning foyer that

  Frank Muccari Cronin & Company Real Estate

  25 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  

  

  /48

  $999,000

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

  4 Camelback Rd, Chester, NY 10918

  Welcome home to 4 Camelback Road. 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

  Alexander Fayn Prominent Properties Sotheby's

  4 Camelback Rd, Chester, NY 10918
• 

  

  /3

  $699,000

  • Land
  • 2 Acres
  • $349,500 per Acre

  50 Elkay Dr, Chester, NY 10918

  Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

  Leib Glanz Point Realty USA

  50 Elkay Dr, Chester, NY 10918
• 

  

  /15

  $1,399,999

  • 4 Beds
  • 4 Baths
  • 4,508 Sq Ft

  145 Kings Highway Bypass, Chester, NY 10918

  A Refined Custom Estate in One of Warwick’s Most Coveted Enclaves. Set on 3.8 private acres and surrounded by similarly distinguished luxury residences, this exceptional custom home offers the rare balance of architectural elegance, lifestyle amenities, and commuter convenience—located within the highly regarded Warwick School District. Offering over 4,500 square feet of beautifully finished

  Courtney Tablante Keller Williams Realty

  145 Kings Highway Bypass, Chester, NY 10918
• 

  

  /8

  $460,000

  • 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, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep 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. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, Chester, NY 10918
• 

  

  /49

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand

  Claudia Lepore Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
• 

  

  /34

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
• 

  

  /20

  $299,999

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

  4508 Whispering Hills, Chester, NY 10918

  Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that

  

  Ammar Iqbal

  eXp Realty

  (845) 668-4564

  4508 Whispering Hills, Chester, NY 10918
• 

  

  /24

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2113 Whispering Hills Unit 178, Chester, NY 10918

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

  Valerie Quinn Keller Williams Realty

  2113 Whispering Hills Unit 178, Chester, NY 10918
• 

  

  /37

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,780 Sq Ft

  108 Pine Hill Rd, Chester, NY 10918

  Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,

  Avi Samet Avion

  108 Pine Hill Rd, Chester, NY 10918
• 

  

  /30

  $289,000

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

  3308 Whispering Hills Dr, Chester, NY 10918

  Welcome to your 2 bedroom, 1.5 bathroom town house condo with a one car garage in the highly desirable Whispering Hills Community in Chester, NY. Well maintained and cared for by its original owner, this unit is located in a nice private section along a green space. The second floor features two spacious bedrooms and one full bathroom. The primary bedroom has cathedral ceilings and a sizable

  Joseph Paoli Howard Hanna Rand Realty

  3308 Whispering Hills Dr, Chester, NY 10918
• 

  

  /35

  $999,999

  • 5 Beds
  • 3.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
• 

  /2

  $199,000

  • Land
  • 7.2 Acres
  • $27,639 per Acre

  0 Oxford Rd Unit KEY946546, Blooming Grove, NY 10918

  7.20 Acre Vacant land, Nice partly cleared and private land

  Chaim Spitzer Blooming Realty

  0 Oxford Rd Unit KEY946546, Blooming Grove, NY 10918
• 

  /2

  $199,000

  • Land
  • 2.6 Acres
  • $76,538 per Acre

  0 Oxford Rd Unit KEY945194, Blooming Grove, NY 10918

  2.6 Acre Vacant land, Nice piece of land

  Chaim Spitzer Blooming Realty

  0 Oxford Rd Unit KEY945194, Blooming Grove, 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
• 

  

  /18

  $299,000

  • 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
• 

  

  /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
• 

  /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
• 

  

  /38

  $449,000

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  71 Greycourt Rd, Chester, NY 10918

  Discover comfort, privacy, and convenience in this beautifully maintained home set on a 2 acre property. Located in a peaceful area, this residence offers a warm and inviting layout with a nicely sized kitchen, three comfortable bedrooms, and two well kept bathrooms.The outdoors is offering a stunning fenced backyard, lots of playground space for entertainment. Minutes to all major highways

  Lazar Schvimmer Blooming Realty

  71 Greycourt Rd, 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
• 

  

  /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
• 

  

  /17

  $309,900

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

  1503 Whispering Hills, Chester, NY 10918

  Lowest priced 3 Bedroom in the complex! This 3 bedroom 2.1 bath end unit is move in with some tlc needed to make it shine! Put your DIY skills to good use! 2 car garage, private patio, central air. Community pool, tennis, playground. close to bus stop, pool and amenities. Easy access to highways Route 17 and the NYS Thruway.

  Darlene Provino Century 21 E & M Williams Rlty

  1503 Whispering Hills, 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
• 

  

  /33

  $289,500

  • 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
• 

  

  /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
• 

  

  /48

  $730,000

  • 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

  (845) 447-0221

  7 Park Place, 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
• 

  

  /93

  $1,750,000

  • 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
• 

  

  /16

  $900,000

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

  32 Fox Hollow Dr, Blooming Grove, NY 10918

  SINGLE LEVEL LIFESTYLE! Discover this Modern Farmhouse Style RANCH on almost 6 acres. Boasting over 3,500 finished sq. ft., this thoughtfully designed home offers 5 spacious bedrooms, one of them set up as a completely private guest quarters located above the oversized 2-car garage, perfect for hosting overnight guests. From the moment you arrive, the eye-catching details and inviting 32 ft long

  

  Julissa Amaro

  Keller Williams Hudson Valley

  (845) 581-2763

  32 Fox Hollow Dr, Blooming Grove, 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
• 

  

  /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
• 

  /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

  $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
• 

  

  /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
• 

  

  /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

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, 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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2