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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

    $6,940 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
  • /37

    $5,500 per month

    • 4 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 4-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
  • /14

    $2,300 per month

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

    4013 Whispering Hills, Chester, NY 10918

    Welcome to this well-maintained 2-bedroom, 1.5-bath townhouse located in Whispering Hills. This unit features an open layout with laminate flooring throughout the main living areas. The living room includes a fireplace and a slider to your own private deck. Enjoy a functional kitchen and dining room that makes everyday living and hosting a breeze. Down the hallway an updated bathroom and two

    Joseph Trifono HomeSmart Homes & Estates

    4013 Whispering Hills, Chester, NY 10918
  • /37

    $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
  • /28

    $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
  • /22

    $2,300 per month

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

    4001 Whispering Hills Unit 463, Chester, NY 10918

    Welcome home to Resort Living! Highly desirable Whispering Hills condo for rent with 2 BR, 1 Bath w/1 car garage End Unit in a Great Location! Open Floor Plan with Hardwood Floors, Cathedral Ceilings, Wood-Burning Fireplace, Central Air, Primary Bedroom has a Huge Walk-In closet and generously sized second bedroom! This condo offers comfort, style and convenience - all on one easy-living level.

    Kristie Jacques Century 21 Full Service Realty

    4001 Whispering Hills Unit 463, Chester, NY 10918
  • /20

    $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
  • /33

    $1,700 per month

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

    13 Railroad Ave, Chester, NY 10918

    FANTASTIC and huge 1 bedroom apartment in the heart of the historic Village of Chester. A second floor unit in the historic American House (a former hotel) with lots of windows for great natural light, and hardwood floors throughout. Private entrance which includes large closet for storage -- then up the stairs to the apartment. Tenant responsible for electric & heat(and Internet/cable/phone,

    Dean Diltz Keller Williams Realty

    13 Railroad Ave, Chester, NY 10918
  • /16

    $2,500 per month

    • 1 Bed
    • 1 Bath
    • 1,768 Sq Ft
    • House for Rent

    21 Murray Dr, Chester, NY 10918

    Introducing a wonderfully spacious one-bedroom apartment on the bottom floor, which offers an impressive 1768 square feet of living space. This apartment features a generously sized bedroom, plenty of closet space and storage, an updated eat-in kitchen with granite countertops, stainless steel appliances, and a full bath, ensuring comfort and convenience. Laundry facilities are available in the

    Carla Terranova Keller Williams Realty

    21 Murray Dr, Chester, NY 10918
  • /14

    $1,600 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
  • /15

    $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
  • /2

    $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

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 10918, 10990, 10950, 10924 and 10926.
How to Rent a Home