Chester Homes under $1 million

Welcome to Chester, New York—an enchanting town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its charming small-town atmosphere, Chester is not just a place to live; it’s a place to thrive, especially for families seeking an excellent education for their children.

One of the standout features of Chester is its highly regarded school district. The Chester Union Free School District is committed to providing a nurturing and academically rigorous environment for students from pre-kindergarten through high school. With dedicated educators and a range of extracurricular activities, students are encouraged to explore their interests and develop their talents. Parents can feel confident that their children are receiving a well-rounded education, preparing them for future success.

For those looking to settle down in this idyllic community, Chester offers a variety of homes priced under $1 million. Whether you're searching for a cozy cottage, a spacious family home, or a charming historic property, Chester has something to suit every taste and budget. The real estate market here is diverse, with many properties boasting beautiful views, ample outdoor space, and proximity to local amenities.

Living in Chester means enjoying a blend of rural charm and modern conveniences, with easy access to hiking trails, parks, and local shops. The community hosts various events throughout the year, fostering a strong sense of belonging among residents. Discover the enchanting lifestyle that awaits you in Chester, where quality education and affordable housing come together to create the perfect place to call home.

Newest Chester Homes under $1 million

$339,900

2 Beds ⋅ 2 Baths ⋅ 1039289 MLS

Discover a compelling combination of space, convenience and Chester accessibility at 3706 Whispering Hills. This 2-bedroom, 2-bath, approximately 1,086-sq-ft townhome-style residence is reported to offer central air, a fireplace, attached garage. Set within the established Whispering Hills community, the location provides convenient access to Route 17, Route 94 and the Chester Park & Ride, along with the Orange County Heritage Trail, Goosepond Mountain State Park and the arts and destinations of the greater Hudson Valley. An appealing alternative for buyers comparing condo and townhome living in Orange County.

3706 Whispering Hills, Chester

$309,000

2 Beds ⋅ 2 Baths ⋅ 1050213 MLS

Welcome to 2107 Whispering Hills, a comfortable 2-bedroom, 1-bath condo offering 1,086 square feet of living space in a convenient Chester location. This home offers an easy, low-maintenance lifestyle with a practical layout and plenty of opportunity to make the space your own. Residents can enjoy community amenities including a swimming pool, providing a great place to relax and enjoy the warmer months without the maintenance of owning a private pool. The condo setting also offers the convenience of having exterior and community maintenance handled for you, allowing more time to simply enjoy your home and surroundings. Whether you're a first-time buyer, downsizing, looking for a weekend getaway, or seeking a low-maintenance home in the Hudson Valley, 2107 Whispering Hills is worth a look. Conveniently located near shopping, dining, parks, and transportation, this home offers a great combination of comfort, convenience, and community living.

2107 Whispering Hills, Chester

$549,000

4 Beds ⋅ 2 Baths ⋅ 1052484 MLS

Bring your vision to **147 Main Street in the Village of Chester**. Zoned **Duplex with Neighborhood Business use**, this spacious property offers an excellent opportunity for investors, business owners or buyers looking to renovate and create value. The property features multiple living areas, four bedrooms, a large kitchen with center island, one full bathroom, a half bathroom, laundry and storage space. An additional apartment includes its own entrance, kitchen, living area, bedroom and full bathroom. Multiple entrances provide flexibility throughout the property. Outside, enjoy several patio areas, a spacious fenced yard, mature trees and off-street parking. Conveniently located in the heart of the Village of Chester, near local shopping, dining, services and major roadways. The property requires repairs and updating and is being offered as an investment and renovation opportunity. Buyers should independently verify all property information, square footage, zoning, permitted uses and certificate-of-occupancy requirements with the Village of Chester.

147 Main Street, Chester

$269,000

2 Beds ⋅ 1 Baths ⋅ 1048656 MLS

Welcome to stress-free Hudson Valley living in the desirable Whispering Hills community! This end unit, bright and airy 2-bedroom, 1-bathroom condo features soaring cathedral ceilings, a cozy fireplace, and an updated kitchen complete with sleek stainless steel appliances. Enjoy fantastic turn-key amenities right outside your door, including two community pools, a clubhouse, gym, tennis, basketball courts, handball, and playgrounds. Conveniently located near major highways and shopping for an effortless commute, you are also just minutes away from local vineyards, Legoland, scenic hiking trails, and everything the vibrant Hudson Valley has to offer.

1212 Whispering Hills, Chester

$299,900

3 Beds ⋅ 2 Baths ⋅ 1051585 MLS

PRICED TO SELL! Bright and spacious 3-bedroom, 2-bath end-unit townhouse in Whispering Hills, offered at an attractive price compared with other condos in the community. Enjoy a cozy fireplace, double patio sliders to a private patio and open yard, generous bedrooms, ample storage, and a private garage with direct entry. Whispering Hills offers resort-style amenities, including a pool, tennis, basketball, dog runs, and fitness center. Conveniently located near Route 17, the NYS Thruway, Route 84, shopping, restaurants, and major attractions. A wonderful opportunity for first-time buyers, downsizers, or investors. Don't miss this value!

1223 Whispering Hills, Chester

$525,000

2 Beds ⋅ 2 Baths ⋅ 1050131 MLS

Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finished basement and finished attic for all your storage needs. Large 2-car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and an oversized deck with an above-ground pool for outdoor enjoyment for all. The home boasts charm and beautiful hardwood flooring throughout many areas of the home. This home is conveniently located near shopping, fine dining, and many leisure activities for all age groups. Easy commute to the city and major transportation hubs for commuters. Local highway and interstate access within minutes. This is a property you want to see; come see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester

$370,000

3 Beds ⋅ 3 Baths ⋅ 1038636 MLS

Welcome home to your beautiful, quiet and peaceful oasis. This 3 bed/3bath unit with a spacious 2-car garage has many new recent updates including new flooring, updated kitchen and bathroom, and an elegant hanging chandelier. Have your morning coffee or evening dinner on your lovely private patio and in the winter enjoy your cozy fireplace. The amenities will give you that vacation resort feel including, tennis and basketball courts, pools, a playground, and a clubhouse with a gym. This Whispering Hills home in this wonderful community and scenic views will surely bring you much pleasure and enjoyment for years to come.

4704 Whispering Hills, Chester

$364,900

3 Beds ⋅ 3 Baths ⋅ 1043986 MLS

WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace! Master Bedroom Suite with Walk In Closet! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Dog Walk! Perfect Commuter Location! Close to Major Highways, Buses & Shopping! Walk to NYC Bus!

2921 Whispering Hills, Chester

$290,000

2 Beds ⋅ 2 Baths ⋅ 1043197 MLS

Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors. Additional updates include a newer furnace, central air conditioning and water heater! Enjoy country club-style living with fantastic community amenities including clubhouses, swimming pools, tennis courts, basketball courts, playgrounds, walking areas and a dog run. An excellent commuter location with NYC bus service right in the complex, plus convenient access to major highways, shopping, restaurants and everyday necessities. Comfort, convenience and community amenities all in one—this is one you won’t want to miss!

1005 Whispering Hills, Chester

$289,000

2 Beds ⋅ 1 Baths ⋅ 1042658 MLS

Welcome to Whispering Hills! This inviting end-unit home overlooks picturesque woodlands, offering a peaceful and private setting while providing a comfortable blend of everyday living and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for those seeking the comfort and tranquility of home without sacrificing accessibility. Come home to a welcoming community and enjoy all that this convenient location has to offer.

2124 Whispering Hills, Chester

$619,999

3 Beds ⋅ 3 Baths ⋅ 1041906 MLS

If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space, flexibility, privacy, and convenience! Step inside to a bright, open-concept main level with soaring vaulted ceilings, a welcoming living room with fireplace, and a dining area featuring custom lighting. The beautifully appointed kitchen offers granite countertops, breakfast island, stainless steel appliances, and direct access to the spacious back deck—perfect for effortless indoor/outdoor entertaining. Three bedrooms are located on the main level, including a spacious primary suite with vaulted ceiling, wall-to-ceiling closets, hardwood floors, and abundant natural light. Two additional bedrooms and convenient main-level laundry complete the first floor. The fully finished lower level is a true bonus, offering endless possibilities with LVP flooring, custom built-in shelving, walk-out access, entertainment space, family room/den, and a bonus room currently used as an office that could easily serve as a guest room or additional sleeping space. A full bath with custom vanity and tiled shower makes this level ideal for guests, extended living, hobbies, or working from home. Outside, enjoy a sprawling yard, mature landscaping, circular driveway, and plenty of room to play, relax, and entertain. The spacious back deck and hot tub create the perfect private retreat. Space, style, flexibility, and location—all in one exceptional property. This is the one you’ve been waiting for!

3561 Rte 94, Chester

$750,000

4 Beds ⋅ 3 Baths ⋅ 1041533 MLS

Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal. Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious kitchen features custom cabinetry, granite countertops, and a custom wine rack with wine fridge, creating a stylish and functional space for everyday living and entertaining. The main level includes a bedroom and full bath for added flexibility, while the spacious primary bedroom offers a private ensuite full bath. The lower level provides additional finished living space with plenty of flexibility for a recreation room, home office, gym, media area, or other needs. Additional interior features include surround sound and smart thermostats. The attached 2-car garage includes an EV charger, while the property also features solar panels leased through Sunrun and a backup generator. Additional highlights include spray foam insulation, central air, on-demand hot water, and forced-air propane heating. Located in a desirable Chester setting, this home offers convenient access to shopping, dining, parks, major roadways, and commuter routes, providing a comfortable setting with everyday convenience.

1 Sanford Avenue, Chester

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