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Chester, NY Homes for Rent

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  • /30

    $3,000 per month

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

    3404 Whispering Hills Unit 44260, Chester, NY 10918

    This spacious 3-bedroom, 2.5-bathroom townhouse in the heart of Chester, NY, offers the perfect balance of comfort and convenience. Nestled in a commuter-friendly location, this home is ideal for those seeking easy access to major highways, while enjoying a peaceful village setting.Step inside to discover a bright, open floor plan featuring laminate floors throughout the main level and a

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    (845) 704-4882

    3404 Whispering Hills Unit 44260, Chester, NY 10918
  • /20

    $6,900 per month

    • 7 Beds
    • 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
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    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Townhouse for Rent

    3911 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This spacious end-unit condo offers 3 bedrooms and 2 full bathrooms, featuring an updated kitchen with quartz countertops, stainless steel appliances, and hardwood floors in the kitchen, dining area, and primary bedroom. The open living room boasts cathedral ceilings and an electric fireplace with a blower, creating a warm and inviting space. The primary suite

    Sean Israelski Howard Hanna Rand Realty

    3911 Whispering Hills, Chester, NY 10918
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    $1,500 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    103 Scott St, Monroe, NY 10950

    Property Id: 2090968Room for Rent - Walton ParkSpacious one and a half room available for rent in a private house located in Walton Park.Ideal for a single person looking for a quiet and comfortable living space.Location: Walton ParkContact: Frank -

    103 Scott St, Monroe, NY 10950
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    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 1,632 Sq Ft
    • Townhouse for Rent

    41 Evan Rd, Warwick, NY 10990

    Spacious and sparkling three floor townhouse located in Kings Estates ! This unit has a finished full sized basement, great closet space and sparkling hardwood floors. The back deck off of the dining room and kitchen area offers a great view. Call for your showing today.

    Christina Biagini Weichert Realtors

    41 Evan Rd, Warwick, NY 10990
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    $2,100 per month

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

    25 Ruscitti Dr Unit 2, Chester, NY 10918

    Discover this delightful 1-bedroom, 1-bathroom ranch-style apartment in a quiet corner of Blooming Grove/Chester. As part of a 2-unit residence, this apartment provides a private and serene living experience. The single-level layout is perfect for easy access and comfortable living. A wonderful opportunity to enjoy a peaceful setting while still being conveniently located.

    Abraham Schwartz Priority Management

    25 Ruscitti Dr Unit 2, Chester, NY 10918
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    $2,600 per month

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft
    • Townhouse for Rent

    1220 Whispering Hills, Chester, NY 10918

    Looking for the perfect rental that is pet (small pet) friendly? Well here you go! This 2 bedroom townhome with an attached one car garage is in the Whispering Hills community known for easy commutes to NYC with buses that come right into the complex. Beautifully renovated unit with a contemporary flair of vaulted ceilings, chocolate Pergo floors, light stone fireplace, new lighting, new

    Karen Taphorn Howard Hanna Rand Realty

    1220 Whispering Hills, Chester, NY 10918
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    $3,400 per month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    21 Sackett Square, Chester, NY 10918

    Picture Perfect Beautiful is this charming ranch style house rental available for immediate occupancy. Enjoy one level living, so you can skip the stairs! Newly renovated, fully detached home situated in commuter friendly Chester and in the Monroe-Woodbury school district. Featuring three bedrooms, two full baths and a large level backyard. Master bedroom suite with full bath. The kitchen

    Courtney Tablante Keller Williams Realty

    21 Sackett Square, Chester, NY 10918
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    $2,550 per month

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

    4706 Whispering Hills, Chester, NY 10918

    Welcome to this beautifully updated residence in the desirable Whispering Hills community, where comfort and convenience come together in a thoughtfully designed home. Featuring 2 bedrooms and 1.5 baths, this property offers a warm and inviting fireplace, an in-unit washer and dryer, generous storage space, and the rare advantage of a private two-car garage. The updates throughout the home

    Nael Dassan Century 21 Elite Realty

    4706 Whispering Hills, Chester, NY 10918
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    $2,550 per month

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Townhouse for Rent

    4612 Whispering Hills, Chester, NY 10918

    Welcome to 4612 Whispering Hills — a spacious, move-in-ready 2-bedroom townhome nestled in the highly sought-after Whispering Hills complex. This home offers the perfect blend of comfort, privacy, and convenience, just minutes from major highways, commuter buses, shopping centers, and more.Step inside through your private entrance and enjoy serene nature views right from your doorstep. The main

    Alissa Taylor-Vetell Keller Williams Realty

    4612 Whispering Hills, Chester, NY 10918
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    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 1,316 Sq Ft
    • Condo for Rent

    3102 Whispering Hills Unit 678, Chester, NY 10918

    CURRENT TENANTE IS SEEKING A ROOMMATE. Looking to rent a fully furnished 1 bedroom with a private bathroom and share the living and kitchen space in a fully air conditioned unit. This would be a month-to-month tenancy and owner is very flexible. Assigned parking spot is available with access to the swimming pool, common area and gym. Located in Chester, NY which is accessible to major

    Stephanie Landeck BHG Real Estate Green Team

    3102 Whispering Hills Unit 678, Chester, NY 10918
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    $5,500 per month

    • 6 Beds
    • 3 Baths
    • 3,066 Sq Ft
    • House for Rent

    3 Grand View Terrace, Chester, NY 10918

    Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

    Shalom Landau eRealty Advisors, Inc

    3 Grand View Terrace, Chester, NY 10918
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    $3,950 per month

    • 4 Beds
    • 2 Baths
    • 3,330 Sq Ft
    • House for Rent

    114 Old Mansion Rd, Chester, NY 10918

    Charming Colonial with 4 Bedrooms on Nearly an Acre – Prime Location! Welcome to this beautifully maintained Colonial-style home nestled on agenerous 0.92-acre lot, offering space, comfort, and convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms,and a versatile layout perfect for modern living. The first floor boasts gleaming hardwood floors, a warm wood

    Chaya Weiss Master Realty Group Inc.

    114 Old Mansion Rd, Chester, NY 10918
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    $2,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft
    • Condo for Rent

    2117 Whispering Hills, Chester, NY 10918

    JUST LISTED * 2 Bedroom Townhome Rental in Whispering Hills * 2 level unit with a 1 Car garage Beautiful Townhome * No Carpets at all - Pergo floos * Spacious & Bright Master Bedroom has Huge Walk in closet * Laundry on main level * Central Air * NYC bus comes in development, Sidewalks too, near Shoprite, CVS, McDonalds ,Mobil & all Highways to NYC * Great location for West Point or NYC Commuter

    Rosalie Cook Weichert Realtors

    2117 Whispering Hills, Chester, NY 10918
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    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 1,258 Sq Ft
    • Apartment for Rent

    15 Railroad Ave Unit 2, Chester, NY 10918

    FANTASTIC and huge 2 bedroom apartment in the heart of the historic Village of Chester. A third floor unit in the historic American House (a former hotel) -- and with either first or second floor access -- with lots of windows for great natural light, and hardwood floors throughout. CENTRAL AIR! Approx. 1,258 square feet, along with a HUGE walk-up attic. There's a small third room which can be an

    Dean Diltz Keller Williams Realty

    15 Railroad Ave Unit 2, Chester, NY 10918
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    $1,500 per month

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

    26 Main St Unit C, Chester, NY 10918

    Live in the heart of historic Chester! This beautiful third floor 1-bedroom, 1-bath apartment is located right on Main Street. Featuring tons of natural light and a private back deck it's the perfect retreat in a vibrant village setting. You'll be steps away from coffee shops, restaurants, and the Heritage Trail, making it easy to enjoy everything Chester has to offer. Commuters will love the

    Brooke Lorimer Keller Williams Realty

    26 Main St Unit C, Chester, NY 10918
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    $2,700 per month

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    62 Main St, Chester, NY 10918

    Tons of square footage in a quiet area with amazing views. With coffe shops , entertainment and restaurants within walking distance , this rental will go quick! Ample parking, a backyard complete with play area, bamboo floors and 5 minutes from commuting highways make this place a unicorn in the real estate world. Come check it out!

    Ryan Case Keller Williams Realty

    62 Main St, Chester, NY 10918
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    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft
    • Townhouse for Rent

    93 Evan Rd, Warwick, NY 10990

    Spacious townhouse located in Kings Estates! This unit offers 3 sizeable bedrooms and 2.5 bathrooms with a sizeable living, dining room, sparkling hardwood floors, granite countertops, and one car garage. Enjoy the use of the backyard and deck during the summertime. Conveniently located near shops, restaurants, and various establishments. Call to book your showing today!

    Christina Biagini Weichert Realtors

    93 Evan Rd, Warwick, NY 10990

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.

Frequently Asked Questions

What are the most popular neighborhoods in Chester, NY for renters?
The most popular neighborhood in Chester, NY for renters is West Ramapo.
What are the most popular zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10990, 10918, 10924, 10950 and 10963.
How to Rent a Home