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Chester, NY Homes for Rent

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  • /20

    $2,550 per month

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

    1912 Whispering Hills Unit 25, Chester, NY 10918

    Move right in to this recently renovated condo. Perfect commuter location, minutes from Route 17. Close to shopping, movies and public transportation. Additional Information: ParkingFeatures:1 Car Attached,

    Agent Photo

    Chris Staritz

    Howard Hanna Rand Realty

    (845) 572-1594

    1912 Whispering Hills Unit 25, Chester, NY 10918
  • /23

    $2,200 per month

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

    82 High St Unit 6, Chester, NY 10918

    This apartment is ready for occupancy. 2 big bedrooms! Primary bedroom offers double closets. The Living room/dining room combination is bright and sun filled with plenty of windows and a patio overlooking a private wooded area. The floors are a grey - vinyl and plush carpet in the bedrooms. The updated Kitchen has stainless steel appliances and a subway tile backsplash. You’ll love the

    Lynda Hoss Weichert Realtors

    82 High St Unit 6, Chester, NY 10918
  • /34

    $3,075 per month

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

    1421 Whispering Hills, Chester, NY 10918

    Step into comfort and style in this beautifully renovated end unit, where modern design meets everyday convenience. Featuring 3 spacious bedrooms, 2.5 sleek bathrooms, and a stunning kitchen with quartz countertops and stainless steel appliances, this home is made for relaxed living and effortless entertaining.Cozy up by the fireplace in the inviting living room, enjoy the convenience of

    Dennis Clark Howard Hanna Rand Realty

    1421 Whispering Hills, Chester, NY 10918
  • /9

    $1,600 per month

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

    13 Jackson St Unit B, Chester, NY 10918

    Enjoy the perfect blend of small-town charm and modern convenience in this inviting 1-bedroom, 1-bath apartment. Ideally located just steps from the Heritage Trail, local coffee shops, and popular restaurants, you’ll love being in the center of it all. This apartment features private off-street parking and easy access to major highways—making both commuting and weekend adventures a breeze.

    Brooke Lorimer Keller Williams Realty

    13 Jackson St Unit B, Chester, NY 10918
  • /6

    $1,500 per month

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

    3102 Whispering Hills Unit 678, Chester, NY 10918

    Current tenant 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 highways.

    Stephanie Landeck BHG Real Estate Green Team

    3102 Whispering Hills Unit 678, Chester, NY 10918
  • /26

    $3,050 per month

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

    3322 Whispering Hills Dr, Chester, NY 10918

    Application accepted. Lease is in process. Recently renovated & move-in ready. This spacious end unit offers updated Kitchen with stainless steel appliances. Bathrooms renovated in 2023. Three spacious Bedrooms, 2.5 Bathrooms, In-unit washer and dryer, 2 car Garage, Private outside fenced patio. Community Amenities: Swimming pool, playground for kids, Tennis court and Basketball courts. Close

    Phyllis Ayres Weichert Realtors

    3322 Whispering Hills Dr, Chester, NY 10918
  • /15

    $1,550 per month

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

    13 Jackson St Unit C, Chester, NY 10918

    Experience the charm of downtown Chester in this warm and welcoming 1 bed, 1 bath apartment. Just a short stroll to the Heritage Trail, local eateries, and cozy cafes, this location puts you right at the heart of village living. This unit includes private off-street parking and a small patio area—perfect for enjoying your morning coffee or some fresh air. With convenient access to major highways,

    Brooke Lorimer Keller Williams Realty

    13 Jackson St Unit C, Chester, NY 10918
  • /19

    $750 per month

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

    7915 State Route 9 Unit 2, Chester, NY 12860

    Basic 1BR/1BA apartment Pottersville! This unit has a large porch and semi-private yard. Exceptionally easy to access from I-87, close to skiing, 20 minutes to Gore, 25 minutes to Lake George. Heat, hot water, sewer and water included in rent. Landlord plows parking lot, tenant is responsible for their walkway. SF estimated. No smoking, no pets. 3x income and renter's insurance required. This

    Jonathan Van Dyk Equitas Realty

    7915 State Route 9 Unit 2, Chester, NY 12860
  • /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
  • /14

    $2,000 per month

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

    1358 Kings Hwy, Sugar Loaf, NY 10981

    Quintessential Sugar Loaf Cottage, newly renovated inside, featuring expansive windows in the front living space, new LVP Flooring throughout, new kitchen with plenty of cabinetry, open shelving and a bar style countertop for extra prep space or entertaining. The space also features an extra large pantry and a new spacious sunlit bathroom with stand up shower. First bedroom is on the main floor

    Christine DeLuca BHG Real Estate Green Team

    1358 Kings Hwy, Sugar Loaf, NY 10981
  • /22

    $3,050 per month

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • House for Rent

    46 Midway Dr, Monroe, NY 10950

    THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous two story home in the Monroe Woodbury School district. Spacious rooms, updated kitchen with plenty of cabinets, four season room fully equipped with new windows and heater can used as office, ample living space, and expansive backyard to enjoy all year round. This lovely home comes with lake rights and all your needs. Call today,

    Eliezer Safdie Sage Realty Center LLC

    46 Midway Dr, Monroe, NY 10950
  • /29

    $2,750 per month

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    582 Lakes Rd, Monroe, NY 10950

    LAKEFRONT LIVING WITH STUNNING VIEWS, BOAT HOUSE & DOCK! Overlooking Walton Lake, this 3 bedroom house offers an abundance of natural light, hardwood floors, natural gas and a cozy wood-burning stove. Visit the restaurants, unique shops and even a movie theater in the Village of Monroe which is only a few miles away. Enjoy fishing, swimming and boating right from your own private dock.

    Carol Buchanan BHG Real Estate Green Team

    582 Lakes Rd, Monroe, NY 10950

Why Live in Chester

Chester is a rural neighborhood known for its rich dairy farming history and as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions, Chester offers a variety of home styles, including single-family homes and larger farmhouses on multi-acre lots. The area is characterized by its park-heavy landscape, with Goosepond Mountain State Park providing 1,500 acres of trails for hiking and horseback riding. Carpenter Community Park serves as a central green space, featuring amenities like a playground, picnic pavilion, and sports courts. The Castle Fun Center offers family-friendly amusement with carnival rides, mini golf, and an indoor roller-skating rink. Chester's Erie Depot, a historic train station now a museum, connects to the Orange Heritage Trail, which runs nearly 20 miles through the county. Local attractions include Legoland, located five miles west in Goshen, and the Capelli Sports Complex, which offers various athletic facilities. Chester Mall provides shopping and entertainment options, while the Chester Agricultural Center offers farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from brick ranch-style and midcentury split-levels to larger contemporary and Craftsman-style homes, with undeveloped lots also available. The Chester Union Free School District serves the area, offering programs like the Healthy Kids Before and After School Program. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87.

Frequently Asked Questions

What are the most popular neighborhoods in Chester, NY for renters?
The most popular neighborhoods in Chester, NY for renters are Blooming Grove, Woodbury, Wallkill, New Windsor and Cornwall.
What are the most popular zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10940, 12550, 12508, 10960 and 07430.
How to Rent a Home