Chester Homes with Washingtonville School district

Welcome to Chester, New York – a picturesque gem nestled in the heart of Orange County. Known for its breathtaking landscapes and vibrant community, Chester is a perfect blend of small-town charm and modern conveniences. With its rolling hills, lush greenery, and access to pristine lakes, this area offers an idyllic setting for families, outdoor enthusiasts, and anyone looking to embrace a tranquil lifestyle.

Chester is not just a place to live; it’s a community where neighbors become friends. The town boasts a variety of local shops, delightful eateries, and seasonal farmers' markets, making it easy to enjoy the best of local culture. The surrounding natural beauty provides ample opportunities for hiking, fishing, and exploring, ensuring that residents can take full advantage of the great outdoors.

For families considering a move, the homes within the Washingtonville School District are particularly appealing. This district is renowned for its commitment to educational excellence, offering a range of programs designed to foster student growth and achievement. Parents can feel confident knowing their children are receiving a quality education in a supportive environment.

Whether you're drawn to Chester's scenic beauty, its tight-knit community, or the outstanding educational opportunities available, this charming town has something for everyone. With a variety of homes to choose from, including cozy cottages and spacious family residences, Chester is the perfect place to call home. Discover the charm of Chester, where every day feels like a retreat, and your next adventure awaits just around the corner.

Newest Chester Homes with Washingtonville School district

$699,000

5 Beds ⋅ 4 Baths ⋅ 1041722 MLS

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 create a warm and welcoming atmosphere. The heart of the home is the expansive open kitchen, featuring modern appliances, generous cabinetry, and plenty of counter space, making it ideal for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, offering both open gathering spaces and cozy nooks. Five generously sized bedrooms provide flexibility and room for everyone. Enjoy the outdoors from the extensive decks overlooking the mature, wooded surroundings, complete with a charming koi pond that adds to the property's peaceful, natural setting. Whether enjoying morning coffee, entertaining guests, or simply unwinding, this outdoor space offers a tranquil retreat. Adding exceptional versatility, a separate approximately 800-square-foot building offers endless possibilities as an art studio, workshop, private office, creative space, or whatever best suits your needs. With its combination of generous living space, distinctive character, privacy, and flex outbuilding space, this property offers a truly special place to call home.

65 Oxford Springs Road, Chester

$459,000

4 Beds ⋅ 3 Baths ⋅ 1039933 MLS

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 gym, playroom for the kids, entertainment room for guests or whatever your needs may be. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with its own full bathroom. Last but certainly not least, is the tranquility and calmness this property has to offer. As you venture outside, you will find yourself tucked away on a quiet road with an inviting backyard that has access to Cromline Creek! This offers the perfect setting for those early morning coffees or long days of entertainment . Add easy highway access, an easy commute to NYC, and proximity to shopping destinations like Woodbury Commons, and you've found a location that truly checks all the boxes. Schedule your showing today and make this beautiful home yours before the new school year begins!

63 Hubshop Road, Chester

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.