Chester Real Estate

Welcome to the Chester School District, a vibrant educational community nestled in the picturesque town of Chester, New York, within the heart of Orange County. Renowned for its commitment to academic excellence, Chester School District serves students from pre-kindergarten through high school, providing a nurturing environment that fosters both intellectual and personal growth.

Chester’s schools are dedicated to delivering a well-rounded education, blending rigorous academic programs with a rich array of extracurricular activities. This ensures that students not only excel in their studies but also develop essential life skills through arts, athletics, and community service initiatives. The district prides itself on small class sizes, allowing for personalized attention and a strong rapport between teachers and students, which enhances the overall learning experience.

Parents in the Chester area appreciate the district's focus on innovation and technology, preparing students for success in an ever-evolving world. With a curriculum that emphasizes critical thinking and problem-solving, students are equipped with the tools they need to thrive in higher education and beyond.

Moreover, Chester is surrounded by breathtaking natural beauty, providing students with ample opportunities for outdoor learning and exploration. The school district actively engages with the community, fostering strong partnerships that enrich the educational experience and encourage parental involvement.

Choosing Chester School District means investing in a bright future for your child. With its strong academic reputation, supportive community, and commitment to excellence, Chester is not just a place to learn—it's a place to grow, thrive, and prepare for a successful tomorrow. Come discover the charm of Chester, where education meets opportunity!

Newest Listings in Chester

$525,000

2 Beds ⋅ 2 Baths ⋅ 1050131 MLS

Welcome to Chester, NY!! Come see this spacious home with features 3 bedrooms and 2 full baths. This home has plenty of possibilities, 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 oversized deck with above ground pool for outdoor enjoyment for all. Home boost with 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 s a property you want to see, comes see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester

$370,000

3 Beds ⋅ 2 Baths ⋅ 1046996 MLS

Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level living in the desirable Whispering Hills community. As soon as you enter the welcoming two-story foyer, you’ll appreciate how bright, open, and impeccably maintained this home is. The spacious open-concept living area features vaulted ceilings and a beautiful Marble & Wood fireplace, creating a warm, inviting atmosphere. Sliding doors lead to your private deck provides easy access to enjoy the peaceful, beautifully landscaped surroundings. The renovated kitchen is both stylish and functional, featuring modern cabinetry, granite countertops, updated backsplash, Stainless appliances and a pantry with plenty of shelving, The spacious primary suite is truly a standout! Enjoy a large walk-in closet with California shelving and a renovated full bath frameless shower. Two additional bedrooms provide plenty of flexibility for guests, a home office, or other needs. Additional updates include sparkling new flooring throughout, new water heater & Washer/Dryer. The attached one-car garage provides convenient direct access to the home along with dedicated storage space. Enjoy all that Whispering Hills has to offer, including a two community pools, tennis court, kids park, dog park, sidewalks, and a peaceful setting—while being just minutes from shopping, restaurants, parks, and major commuter routes. Located in the Chester School District. All this with New York City bus that picks up and drops off right in the complex. Don't miss your opportunity to make it yours. Call today for your private tour. *****Professional Photos Coming Soon****

3211 Whispering Hills, Chester

$380,000

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

$374,900

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

$25,000

1043650 MLS

Convenience store for sale located in the Village of Chester. Business only for sale. Lease is $1,700 per month.

6 Main Street, 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

$550,000

3 Beds ⋅ 2 Baths ⋅ 1042882 MLS

Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an effortless connection to the serene backyard perfect for relaxing, entertaining, or enjoying the surrounding nature. The spacious primary suite features a huge closet and a private master bath. Two additional bedrooms offer generous closet space, providing plenty of room for family, guests, or a home office. Step outside and cross the charming bridge over the stream to access the enlarged backyard, offering even more space to enjoy the outdoors. A spacious 24' x 28' detached garage with a 10' x 10' garage door provides ample room for large vehicles, ATVs, a workshop, equipment, and storage. Conveniently located just minutes from Route 17, shopping, restaurants, and everyday amenities, this property offers the perfect blend of country tranquility and convenient access to town.

50 Hambletonian Avenue, Chester

$299,000

2 Beds ⋅ 1 Baths ⋅ 1042658 MLS

Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to offer.

2124 Whispering Hills, Chester

$649,999

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

$360,000

3 Beds ⋅ 3 Baths ⋅ 1032618 MLS

Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain with a new HVAC system. The kitchen boasts modern stainless-steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the community pool, play a match on the tennis courts, or hit the gym for your daily workout. There are also handball courts and beautifully landscaped surroundings that make everyday living feel like a getaway. With a prime location, you’re never far from shopping, dining, and recreation options.

3409 Whispering Hills, Chester

$475,000

4 Beds ⋅ 2 Baths ⋅ 1040785 MLS

Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors. Conveniently located close to shopping, dining, and major highways, this home offers a great combination of space, comfort, and accessibility. Don't miss the opportunity to make it yours!

32 Surrey Road, Chester

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