Chester Homes with Chester School district

Welcome to Chester, New York – a charming town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its stunning natural beauty, Chester is surrounded by the breathtaking views of the Hudson Valley and the majestic Catskill Mountains, making it an ideal destination for nature lovers and outdoor enthusiasts alike.

Chester offers a delightful blend of small-town charm and modern conveniences. With a rich history dating back to the 18th century, the town boasts a quaint downtown area filled with unique shops, cozy cafes, and local eateries, all contributing to its warm and inviting atmosphere. The community is known for its friendly residents who take pride in their town, making it a welcoming place for families and newcomers.

One of the highlights of Chester is its highly regarded school district. The Chester School District is committed to providing quality education, fostering a nurturing environment that encourages academic excellence and personal growth. Families looking to settle down in this area can find a variety of homes that cater to different lifestyles, from charming historic houses to modern family residences.

Living in Chester means enjoying the best of both worlds: a peaceful suburban lifestyle with easy access to the cultural and recreational offerings of nearby cities. Whether you’re hiking the scenic trails, exploring local parks, or participating in community events, Chester is a place where you can truly feel at home. Come discover the beauty and warmth of Chester, NY, and see why it’s the perfect place to call home!

Newest Chester Homes with Chester School district

$370,000

3 Beds ⋅ 1 Baths ⋅ 1033159 MLS

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 to the village!

33 Meadow Avenue, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031147 MLS

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 kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

3 Hilltop Lane, Chester

$279,999

2 Beds ⋅ 2 Baths ⋅ 1030827 MLS

Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two generously sized bedrooms and a full bath, while a convenient first-floor powder room is perfect for guests. Additional features include an attached two-car garage and access to Whispering Hills’ outstanding amenities, including a swimming pool, clubhouse, tennis courts, and basketball courts. Conveniently located close to shopping, restaurants, and major highways, this home offers easy, low-maintenance living with an unbeatable location.

2007 Whispering Hills, Chester

$350,000

4 Beds ⋅ 1 Baths ⋅ 1031155 MLS

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! Close to shops and restaurants! Great commuter location! Come preview today!

151 Main Street, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031045 MLS

1 Hilltop Lane, Chester

$315,000

2 Beds ⋅ 2 Baths ⋅ 1027838 MLS

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 entertaining.The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs,the primary bedroom offers vaulted ceilings,a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample size with a double door closet. A skylight in the hallways brightens the home. Additional features and highlights include central air, natural gas heating, an attached one car garage with extra storage, building roof replaced in 2022, HVAC 2013, skylight 2013, municipal water and sewer,reasonable hoa fees, snow removal and beautifully maintained grounds. Community amenities feature a dog park, playground, two pools, a gym and more. Just 5 minutes from the heart of Chester where you'll find local shopping,dining and entertainment all while remaining 70 miles from NYC, 10 minutes to LegoLand and close to Woodbury Common, Resorts Casino and Bethel Woods Concert Venue. Visit our nearby breweries, cafes,farmer market and historic Sugarloaf Village. Come see why everyone wants to live here!

4008 Whispering Hills Drive, Chester

$599,900

3 Beds ⋅ 2 Baths ⋅ 1029645 MLS

Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.

50 Hambletonian Avenue, Chester

$575,000

6 Beds ⋅ 2 Baths ⋅ 992189 MLS

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 Second beautiful structure offers hardwood floors, as seen, 2 bedrooms, a kitchen, a living room, and 1 full bath. In addition, there is a garage about 750 sq that can be rented out for another few hundred dollars a month. Enjoy the beautiful 1.1-acre property. This unique property has multiple opportunities!

68 Conklingtown Road Unit #1&2, Chester

$389,900

3 Beds ⋅ 2 Baths ⋅ 1027245 MLS

WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door) perfect for outdoor enjoyment and relaxation overlooking the pretty landscape. The kitchen has been thoughtfully renovated with new modern cabinetry, quartz countertops, updated backsplash, newer appliances (dishwasher, gas range and microwave), dedicated pantry with roll outs and ample shelving, new sink and pull out garbage drawer. Through the main entry level you have immediate access to the 1 car garage, which also has a dedicated storage space. This home has its own private entrance and the two story foyer offers a warm welcome to the unit. Notice how well maintained this home is as you tour. The primary bedroom is spectacular. This room is spacious and it has a large walk in closet and a gorgeous newly designed on suite full bathroom that feels like a "spa". Throughout the home, new flooring and window blinds have been installed, along with recessed lighting and a modern dining room chandelier. An added perk is that the entire condo was freshly painted in 2023. Further, additional significant updates offering peace of mind for years to come include: New furnace (2022) and new air conditioning unit (2023). There is also a smart thermostat system. This property is located in the Chester school district. Whispering Hills is an in-demand location - just minutes from shopping, restaurants, parks and more. Also, you'll love the easy access to main routes while enjoying the peaceful setting this development has to offer! Within Whispering Hills is the community pool for Summer fun, tennis court and sidewalks. Call for your private tour. Welcome home! *Special features sheet with more details and a floor-plan are available*

4114 Whispering Hills, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1025992 MLS

2 Hemlock Court, Chester

$350,000

3 Beds ⋅ 3 Baths ⋅ 1025165 MLS

Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and entertaining. Enjoy your own private patio with exceptional privacy—ideal for relaxing or hosting guests. A two-car garage provides ample parking and storage. Located in the highly desirable Whispering Hills community with access to outstanding amenities, and just minutes from shopping, restaurants, parks, commuter transportation, and Routes 17 and 94. This turnkey home combines convenience, low-maintenance living, and an unbeatable location. Don't miss this opportunity—schedule your showing today!

2604 Whispering Hills, Chester

$399,999

4 Beds ⋅ 2 Baths ⋅ 1024779 MLS

Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, Chester

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