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Chester, NY Homes for Rent

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  • /29

    $2,400 per month

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

    3917 Whispering Hills, Chester, NY 10918

    TWO-LEVEL RENTAL in Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances as well as a convenient in-unit washer and dryer. The first level offers a stylish half bath and brand-new flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio.

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 460-1589

    3917 Whispering Hills, Chester, NY 10918
  • /20

    $11,797 per month

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $11,797/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
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    $1,900 per month

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

    2 Oak St, Chester, NY 10918

    Freshly updated and well-maintained 2 bedroom unit in a multi-family home. Open concept living space with kitchen, dining space and living room. Beautiful view of the Chester farmlands from the living room. Two nicely sized bedrooms with large closets. Separate entrance for tenant, access to side yard in front of unit, tenant gets space in the driveway for 2 cars. Landlord pays heat, hot water,

    Elissa Elliott Howard Hanna Rand Realty

    2 Oak St, Chester, NY 10918
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    $5,300 per month

    • 4 Beds
    • 2 Baths
    • 3,412 Sq Ft
    • House for Rent

    66 Murray Dr, Chester, NY 10918

    Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer

    Tehillah Deslandes Howard Hanna Rand Realty

    66 Murray Dr, Chester, NY 10918
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    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 944 Sq Ft
    • House for Rent

    492 Black Meadow Rd, Chester, NY 10918

    Looking for a quiet rental with privacy? This rental is on the ground level - no stairs! Large sun filled living space, and one bedroom. Large full bathroom, and a storage room for everything. Tons of parking!

    Jennifer Gillett Howard Hanna Rand Realty

    492 Black Meadow Rd, Chester, NY 10918
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    $3,700 per month

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • House for Rent

    12 Juniper Ln, Monroe, NY 10950

    Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for guests, or a

    Danielle Riggs Keller Williams Hudson Valley

    12 Juniper Ln, Monroe, NY 10950
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    $6,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,348 Sq Ft
    • House for Rent

    20 Goshen Rd, Chester, NY 10918

    Rare rental opportunity to occupy a premier estate in Chester. This property is perfectly suited for those seeking a self-sufficient lifestyle without sacrificing modern luxury. The 4-bedroom, 3-bath custom home is complemented by expansive grounds crisscrossed with miles of private horse trails and a thriving, mature fruit orchard. Practicality meets scale with an infrastructure designed for

    Ramanjit Dhanoa eXp Realty

    20 Goshen Rd, 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

    ***Rare opportunity***Available April 1st for occupancy! 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,

    Robert Addon Keller Williams Realty

    408 Bull Mill Rd Unit 2, Chester, NY 10918
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    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    204 Pine Hollow Way, Chester, NY 10918

    Highly desirable one bedroom apartment for rent! Spacious open concept unit with lots of natural light! Relax on your own private patio and enjoy the peaceful surroundings of the outdoors. Large bedroom with great closet space! This unit has a private laundry room with hook ups. Close to all shopping, restaurants, apple picking, wineries, breweries & everything the beautiful Hudson Valley has to

    Kristie Jacques Century 21 Full Service Realty

    204 Pine Hollow Way, Chester, NY 10918
  • /9

    $2,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • House for Rent

    71 Greycourt Rd, Chester, NY 10918

    Lovely and Private! Welcome to 71 Greycourt rd. this house is conveniently located just in the right location being close to major highways and shopping! This home was recently renovated with lots of upgrades. nice size kitchen, upgraded electricity, and much more! This house is private, sitting on a 2-acre property and a fenced-in yard for total privacy. This house is your dream rental! Don't

    Mordechai Ungar HFA Realty Group

    71 Greycourt Rd, 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
  • /10

    $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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    $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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    $3,050 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
  • /2

    $2,850 per month

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

    2104 Whispering Hills, Chester, NY 10918

    Experience the best of Whispering Hills in this expansive 3-bedroom, 2.5-bathroom townhouse—the largest model available in the community! Currently undergoing a fresh renovation, this home will be move-in ready by April 15, 2026. The layout features a spacious master suite complete with a private walk-in closet, perfect for your wardrobe needs. Located just minutes from premier shopping, dining,

    Jayne M. Prechtel Keller Williams Valley Realty

    2104 Whispering Hills, Chester, NY 10918
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    $2,700 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Property for Rent

    112 Scott St, Monroe, NY 10950

    A truly charming place to call home! Beautiful open concept home for rent featuring an airy floor plan with abundant windows that fill the space with natural light. This inviting property offers a lovely dining area, a spacious primary bedroom with its own private bath, and generous closet space thru-out, a washer/dryer, a nice relaxing deck and so much more. The home can be rented partially

    Sy Mujovic I Realty LLC

    112 Scott St, Monroe, NY 10950
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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, 10924, 10950 and 10987.
How to Rent a Home