16

Chester, NY Homes for Rent

Section Image Section Image
  • /37

    $2,950 Per Month

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

    2722 Whispering Hills Unit 542, Chester, NY 10918

    New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym,

    Agent Photo

    Erin Connolly-Frontino

    Artisan Realty

    (845) 385-1695

    2722 Whispering Hills Unit 542, Chester, NY 10918
  • /7

    $4,000 Per Month

    • 6 Beds
    • 2 Baths
    • House for Rent

    5 Laroc Rd, Chester, NY 10918

    Property Id: 1802590Stunning Home with Expansive Yard and Abundant Storage!Welcome to this incredible property, boasting a massive backyard perfect for outdoor entertaining! Enjoy warm weather gatherings on the spacious deck, and make the most of the two sheds for storing tools, equipment, and more.This fantastic home also features:- 1 garage for secure vehicle

    (845) 572-1279

    5 Laroc Rd, Chester, NY 10918
  • /20

    $2,695 Per Month

    • 3 Beds
    • 1 Bath
    • 2,386 Sq Ft
    • Apartment for Rent

    28 Academy Ave Unit 2, Chester, NY 10918

    Available for Rent! Spacious 3-bedroom, 1-bath second-floor apartment located in the heart of Chester. This well-maintained unit features a finished attic, providing additional flexible living space perfect for a home office, playroom, or storage. Conveniently located close to shopping, restaurants, parks, schools, and major commuter routes. Enjoy all that the Village of Chester has to offer

    Agent Photo

    Ammar Iqbal

    eXp Realty

    (845) 493-3043

    28 Academy Ave Unit 2, Chester, NY 10918
  • /6

    $2,000 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    7 Kennedy Ln Unit 3, Monroe, NY 10950

    Property Id: 2505575Welcome to this well-kept 1 bedroom + extra bonus room apartment located at — perfect for anyone needing a little extra space for a home office, guest room, or creative setup.•1 large bedroom + versatile bonus room•Private front & back entrances•Covered patio + backyard access•Small private yard space•Metal shed for extra storage•Off-street

    (845) 604-9599

    7 Kennedy Ln Unit 3, Monroe, NY 10950
  • /12

    $2,100 Per Month

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

    1358 Kings Hwy, Chester, NY 10918

    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 Corcoran Baer & McIntosh

    1358 Kings Hwy, Chester, NY 10918
  • /31

    $3,795 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • Spacious Mountain View Home in Sugar Loaf – Pet Friendly & Move-In Ready

    4 Wright Rd, Chester, NY 10918

    Welcome to this beautifully maintained home nestled in a quiet, family-friendly neighborhood with stunning mountain views. Located less than a 10-minute walk from Valkyrie Coffee, the Indigo Collective salon, and the heart of Sugar Loaf, you'll enjoy easy access to unique shops, restaurants, and local attractions. The village's annual May festival transforms the streets into a vibrant

    4 Wright Rd, Chester, NY 10918
  • /38

    $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
  • /37

    $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
  • /16

    $2,670 Per Month

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

    1907 Whispering Hills, Chester, NY 10918

    Welcome home to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. Enjoy a cozy fireplace in your spacious living room, kitchen with tile flooring for easy cleanup, and a patio right outside your front sliding doors for summer night enjoyment after taking a dip in the community pool.

    Erin Hansford Stonewall Realty Group LLC

    1907 Whispering Hills, Chester, NY 10918
  • /13

    $2,900 Per Month

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

    168 Pine Hill Rd Unit 1, Chester, NY 10918

    INLCUDES UTILITIES, HEAT & HOT WATER!! Welcome to Unit #1 of 168 Pine Hill Rd. This lovely three bedroom, 1.5 bath apartment offers beautiful views with lots of natural light, an eat in kitchen with stainless steel refrigerator and stove (gas) as well as washer and dryer for added convenience, 3 nice sized bedroom. Easy access- no steps to enter the two level unit. There is a wrap around driveway

    Claudia Lepore Keller Williams Realty

    168 Pine Hill Rd Unit 1, Chester, NY 10918
  • /12

    $3,399 Per Month

    • 4 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • House for Rent

    8 Hickory Ln, Monroe, NY 10950

    Single-family spacious bi-level in a beautiful neighborhood in Monroe. Private In Law Suite Own Entrance No Stairs fully-equipped ,The main floor offers an open living and dining room three nice size bedrooms and a full bath and kitchen with appliances, The lower level has a private entrance and a beautiful size family room and a bedroom plus an office room and kitchen with

    Eliezer Safdie Sage Realty Center LLC

    8 Hickory Ln, Monroe, NY 10950
  • /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
  • /22

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,699 Sq Ft
    • Townhouse for Rent

    256 Heritage Ln, Monroe, NY 10950

    Monroe, NY - Spacious, two-level townhouse end unit. First floor features living room/dining area, kitchen with dinette area, half bath, laundry room & garage. Top level contains master bedroom suite with full bath & walk-in closet, second bedroom, third bedroom, second full bathroom and hallway walk-in closet. Additional features: Young carpeting, entry way flooring, butcher block counter top &

    Frank Gomez HomeSmart Homes & Estates

    256 Heritage Ln, Monroe, NY 10950
  • /13

    $2,800 Per Month

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

    27 Midway Dr, Monroe, NY 10950

    Charming Ranch home is waiting for you! Super condition! Beautiful perfectly maintained kitchen, 3 Bedrooms and 1 full bath. Enjoy the secluded deck surrounded with beautiful greenery! This Home has Walton Lake rights! Schedule your tour today!

    Joseph Rosenfeld Flag Realty Group

    27 Midway Dr, Monroe, NY 10950
  • /33

    $2,900 Per Month

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

    1502 Whispering Hills, Chester, NY 10918

    Beautiful 3 bedrooms and 2 baths in Whispering Hills. Updated and freshly painted. New carpeting. Fire place and vaulted ceiling.Enjoy resort style living with pools, tennis courts, club house, gym, playgrounds and basketball courts. Located close to major highways for an easy commute. Additional Information: ParkingFeatures:1 Car Attached,Storage: Garage,

    Nikki Grzegorzewski Keller Williams Realty

    1502 Whispering Hills, Chester, NY 10918
  • /43

    $3,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Apartment for Rent

    1403 Kings Hwy, Chester, NY 10918

    Luxury Farmhouse Rental in the Heart and Soul of Sugar Loaf – Warwick Schools! Experience country luxury at its finest in this stunning farmhouse rental located in the charming hamlet of Sugar Loaf. Designed for those who appreciate quality craftsmanship and timeless character, this exceptional home offers approximately 3,200 square feet of beautifully appointed living space. Step inside to

    Carla Terranova Keller Williams Realty

    1403 Kings Hwy, 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

How much does it cost to rent a home in Chester, NY?
The median rent for a home in Chester, NY is $3,372 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Chester, NY?
To comfortably afford the median rent in Chester, NY, a household needs to earn roughly $134,880 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $3,372 per month in Chester, NY, renters typically need to show $10,116 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chester, NY?
In Chester, NY, the price-to-rent ratio is 12.3, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Trends in Chester, NY

Rental Home Trends

Number of Homes for Rent
16
Median Rent
$3,372
Median Single Family Home Rent
$2,750
Median Townhouse Rent
$2,550
Median Condo Rent
$1,750
How to Rent a Home