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Chester, NY Homes for Rent

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  • /20

    $8,435 per month

    • 7 Beds
    • 5.5 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

    Escape to this luxurious 7-bedroom home in Chester, NY, designed for ultimate relaxation. This spacious home features stylish furnishings and elegant touches throughout, making you feel at home.This home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy a game room with a pool table, a spacious dining room, a gas fireplace, a powder

    45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918
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    $3,800 per month

    • 4 Beds
    • 3 Baths
    • 2,457 Sq Ft
    • House for Rent

    118 Booth Rd, Chester, NY 10918

    A tastefully, restored 2-story, 4BR, 3BTH, bi-level style home set on over 3+ prestine acres at the end of a quaint cul-de-sac. Enjoy the large open fields, secluded from all the stresses of the day. Plenty of room for an athletic field, in-ground pool or just a peaceful sanctuary. The exquisite touches throughout add to its elegance, from high-end ceramics to restored oak floors. The

    Chris Scibelli Keller Williams Realty

    118 Booth Rd, Chester, NY 10918
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    $2,200 per month

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

    82 High St Unit 5, Chester, NY 10918

    Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

    Lynda Hoss Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
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    $1,700 per month

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

    8 Main St, Chester, NY 10918

    Located in Historic Downtown Chester. This is a 1 bedroom apartment located on the 2nd floor. Open floor plan with exposed brick walls and lots of natural light. Walking distance to shops, restaurants, brewery, and the Heritage Trail. Close to public transportation and Route 17.

    Jeanmarie Valentin HomeSmart Homes & Estates

    8 Main St, Chester, NY 10918
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    $1,600 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 cafés, 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. This unit is situated on quiet Jackson

    Brooke Lorimer Keller Williams Realty

    13 Jackson St Unit C, Chester, NY 10918
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    $2,300 per month

    • 3 Beds
    • 1 Bath
    • 866 Sq Ft
    • House for Rent

    2 Oxford Depot, Chester, NY 10918

    Well-maintained 3-bed Chester, NY....This home is meticulous and move-in ready! Rent this home and be close to everything! Just a few minutes to the highway, close to commuter bus train, and less than an hour to GWB! Popular heritage trails are 100 yards away for biking, walking, and running. Additional Information: Heating Fuel Oil Below Ground,

    Mordechai Ungar HFA Realty Group

    2 Oxford Depot, Chester, NY 10918
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    $2,000 per month

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

    1396 Kings Hwy, Chester, NY 10918

    Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday

    Roxanne Hartman Timothy W. Kramer

    1396 Kings Hwy, Chester, NY 10918
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    $1,900 per month

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    347 Bellvale Rd, Chester, NY 10918

    Move-in ready rental in beautiful Warwick, NY. This spacious apartment-style home is nestled in a peaceful countryside setting and is available for a full-time tenant. Enjoy comfortable one-level living with scenic nature views in every direction.Upon entry, you are welcomed by a large foyer that leads into a sun-soaked living room, perfect for relaxing or entertaining. Just off the living

    Alissa Taylor-Vetell Keller Williams Realty

    347 Bellvale Rd, Chester, NY 10918
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    $2,450 per month

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

    1107 Whispering Hills, Chester, NY 10918

    Great 2bd 1.5ba Townhouse style unit in Whispering Hills. Living room w/ fireplace open to the dining room. Laminate floors throughout. We’ll appointed kitchen with newer cabinets and SS appliances. Vaulted Ceilings in the Master Bedroom with walk-in closet and organizer. Central air, TWO car garage, Washer/Dryer! This complex offers 2 community pools, clubhouse, tennis/basketball courts and gym.

    Joseph Trifono HomeSmart Homes & Estates

    1107 Whispering Hills, Chester, NY 10918
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    $3,850 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Apartment for Rent

    408 Bull Mill Rd Unit 2, Chester, NY 10918

    Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms, thoughtfully laid out to maximize comfort and natural light.

    Robert Addon Keller Williams Realty

    408 Bull Mill Rd Unit 2, Chester, NY 10918
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    $1,950 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
    • 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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    $2,850 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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    $2,700 per month

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

    47 Helene Rd, Warwick, NY 10990

    Great spacious end unit townhouse in Kings Estates ! Freshly painted with professionally cleaned carpets makes this townhouse move in ready! This unit has been renovated within the last few years and includes newer stainless steel appliances and hardwood floors throughout the living and dining room. Back deck off of the dining room and kitchen area offers a GREAT view. Must see to appreciate !

    Christina Biagini Weichert Realtors

    47 Helene 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 zip codes in Chester, NY for renters?
The most popular zip codes in Chester, NY for renters include 10918, 10990, 10950, 10921 and 10924.
How to Rent a Home