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Chester, NY Homes for Rent

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  • /29

    $8,970 per month

    • 7 Beds
    • 5.5 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

    Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918
  • /21

    $2,150 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    12 Railroad Ave Unit Floor 2, Chester, NY 10918

    Is there a 2-bed apartment in Chester Village with parking, outdoor space, and walkable access to downtown? This newly refreshed second floor rental offers approximately 1,000 square feet, a private covered deck, garage parking, and an updated kitchen, all set in Historic Downtown Chester near dining, shops, and the Heritage Trail. This spacious apartment at 12 Railroad Avenue, Unit Floor 2

    Geoffrey Green BHG Real Estate Green Team

    12 Railroad Ave Unit Floor 2, Chester, NY 10918
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    $3,200 per month

    • 4 Beds
    • 2 Baths
    • House for Rent

    3 Tulip Ln, Monroe, NY 10950

    Property Id: 2288513Your Ideal Home Awaits;Section 8 Accepted! Enjoy the comfort of this stunning apartment, featuring 4 spacious bedrooms and 2 full baths. Bright, Airy Spaces;Key Features• 4 generous bedrooms• 2 full bathrooms• Large deck• Convenient location near amenitiesExperience the perfect balance of space and style in your new home.Call to

    3 Tulip Ln, Monroe, NY 10950
  • /29

    $3,300 per month

    • 4 Beds
    • 1.5 Baths
    • 1,605 Sq Ft
    • House for Rent

    98 Main St, Chester, NY 10918

    Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

    Eveline White Hudson Valley Griffith

    98 Main St, Chester, NY 10918
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    $2,950 per month

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Townhouse for Rent

    4321 Whispering Hills, Chester, NY 10918

    This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways and rail for commuters. Freshly painted, new carpets, hardwood floors redone. Must see if you are looking to rent!!! Additional Information: ParkingFeatures:1 Car Attached.

    Dan Neil Field Pointe Realty LLC

    4321 Whispering Hills, Chester, NY 10918
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    $2,450 per month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    3607 Whispering Hills Unit 295, Chester, NY 10918

    Don't miss the opportunity to lease this picture-perfect, beautifully renovated townhome featuring two bedrooms and 1.5 brand-new bathrooms. The residence boasts a brand-new kitchen outfitted with stainless steel appliances and includes a dedicated laundry room with a new washer and dryer. Upstairs, the space is brightened by a cathedral ceiling and skylight, adding an airy and luxurious feel.

    Nikki Grzegorzewski Keller Williams Realty

    3607 Whispering Hills Unit 295, Chester, NY 10918
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    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Townhouse for Rent

    2910 Whispering Hills Dr, Chester, NY 10918

    Welcome to Whispering Hills Chester's highly desirable condo community offering comfort, convenience, and lifestyle! This spacious 3-bedroom, 2.5-bathroom unit features soaring ceilings, generous room sizes, and excellent storage throughout. The stylish kitchen boasts brand-new appliances and modern two-tone cabinets, creating a sleek and inviting space that opens to a private deck ideal for

    Nathen Singer MK Realty Inc

    2910 Whispering Hills Dr, Chester, NY 10918
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    $3,950 per month

    • 4 Beds
    • 2.5 Baths
    • 2,840 Sq Ft
    • House for Rent

    948 Craigville Rd, Chester, NY 10918

    Amazingly beautiful 1850's renovated home and horse property. Over 11 acres of land with approx. 3.5 acres of 4-board fenced-in pasture including 2 run-in sheds with access to water. The house is in excellent condition with high-efficiency radiant heated floors, central a/c and natural gas! There is also a stand-by generator. Enjoy beautiful wide-plank wood floors, meticulously maintained and

    Layla Rose Boyles Century 21 Realty Center

    948 Craigville Rd, Chester, NY 10918
  • /11

    $2,650 per month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    1418 Whispering Hills, Chester, NY 10918

    Looking for a 2 car garage? Look no further! Welcome to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. The first level offers a cozy fireplace in your spacious living room, dining area with sliding glass doors to your private patio, kitchen, half bath, and washer/ dryer. You will

    Erin Hansford Stonewall Realty Group LLC

    1418 Whispering Hills, Chester, NY 10918
  • /7

    $1,700 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    8 Main St, Chester, NY 10918

    Conveniently located in the Village of Chester, this spacious one-bedroom apartment is close to all amenities and Route 17. It is situated on the 3rd floor and features an open floor plan with exposed brick walls, providing plenty of natural light and windows.

    Jeanmarie Valentin HomeSmart Homes & Estates

    8 Main St, Chester, NY 10918
  • /6

    $2,450 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • House for Rent

    2208 Whispering Hills, Chester, NY 10918

    Welcome to 2208 Whispering Hills! This stunning townhouse will capture your heart with its impeccable features and unbeatable location. Step inside and be welcomed by the warm and inviting atmosphere. The main level boasts a beautifully designed open floor plan, allowing for seamless flow between the living room, dining area, and kitchen. Newer tiles in the kitchen, you'll find 2 bedrooms, each

    Mordechai Ungar HFA Realty Group

    2208 Whispering Hills, Chester, NY 10918
  • /13

    $3,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    25 Trotting Dr, Chester, NY 10918

    Welcome to 25 Trotting Drive, located in the heart of Chester, NY. This spacious rental offers the perfect blend of comfort and convenience with plenty of room for everyday living. The home is set in a quiet residential neighborhood, providing a peaceful setting with easy access to local shopping, schools, and major highways. Tenants will be responsible for all utilities. Trash collection & Lawn

    Anthony Rivas Keller Williams Hudson Valley

    25 Trotting Dr, Chester, NY 10918
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    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    82 High St Unit 2, Chester, NY 10918

    This ground-floor apartment is ready for occupancy. The Primary bedroom has double closets and can fit a king-sized bed. The Living room/dining room combination is bright and sun-filled, with plenty of windows and a patio overlooking a private wooded area. The flooring is grey vinyl, and there is plush carpet in the bedrooms. The updated kitchen has stainless steel appliances and a subway tile

    Lynda Hoss Weichert Realtors

    82 High St Unit 2, Chester, NY 10918
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    $2,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Townhouse for Rent

    2805 Whispering Hills Unit 573, Chester, NY 10918

    2BD 1.5BA rental in Whispering Hills! This unit has been updated top to bottom, featuring LVP flooring throughout, new refrigerator, new stove and a brand new full bath! The entire space has been professionally painted and feels like new. Updated kitchen including newer cabinets and granite countertops. The master bedroom offers a walk in closet. Washer and dryer in unit and private garage. The

    Joseph Trifono HomeSmart Homes & Estates

    2805 Whispering Hills Unit 573, Chester, NY 10918

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

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