10

Chester, NY Homes for Rent

Section Image Section Image
  • /4

    $4,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,894 Sq Ft
    • House for Rent

    3 Brookside Ave, Chester, NY 10918

    Come see this mixed use residential and commercial property for rent. Enjoy the benefits of working from home as you can have your business in the same home. 3 bed 3 bath home in Chester. Enjoy the ample amount of parking available, fitting well over 10 cars on your lot. Call today for a showing

    Agent Photo

    Joel Ayala

    HomeSmart Homes & Estates

    3 Brookside Ave, Chester, NY 10918
  • /20

    $16,214

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $16,214/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 11, 2027.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
  • /20

    $2,300 Per Month

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

    82 High St Unit 5, Chester, NY 10918

    Fresh carpet has just been laid throughout this luminous top-floor penthouse, where an open layout and abundant sunshine create an inviting canvas for daily life. At 900 square feet, this 2-bedroom, 1-bath home balances spaciousness with a cozy, lived-in warmth. Cooks will appreciate the updated kitchen, outfitted with a new stainless steel refrigerator and dishwasher that bring both style and

    Agent Photo

    Ourania Pizzolato

    Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
  • /10

    $1,750 Per Month

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

    105 Pine Hollow Way, Chester, NY 10918

    Welcome to the desirable Pine Hollow Complex in Chester! This spacious one-bedroom, one-bath residence offers a bright, open-concept floor plan filled with natural light, creating a warm and inviting atmosphere. The open living area features a gas fireplace and central air conditioning, providing comfort throughout every season. The generously sized bedroom offers generous closet space, while a

    Kristie Jacques Century 21 Full Service Realty

    105 Pine Hollow Way, Chester, NY 10918
  • /5

    $3,350 Per Month

    • 4 Beds
    • 3 Baths
    • 1,134 Sq Ft
    • Condo for Rent

    616 Lakes Rd, Monroe, NY 10950

    Beautifully and freshly redone. Has amazing water views from both floors windows!!!

    616 Lakes Rd, Monroe, NY 10950
  • /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
  • /14

    $2,350 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 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
  • /22

    $3,250 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
  • /6

    $1,600 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 1 bath. This is within the 3 bedroom unit and common area/kitchen will be shared with the owner. This is 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

    Stephanie Landeck BHG Real Estate Green Team

    3102 Whispering Hills Unit 678, Chester, NY 10918
  • /24

    $2,950 Per Month

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

    35 Helene Rd, Warwick, NY 10990

    Welcome to Kings Estates! This updated end-unit townhome offers the perfect combination of comfort, style, and convenience. Featuring 3 bedrooms and 2.5 bathrooms, this move-in-ready home showcases an updated kitchen with newer appliances, hardwood floors throughout, and a thoughtfully finished basement that provides additional living and entertaining space. The spacious backyard is a true

    Ishadar Garvey KW Hudson Valley United

    35 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

How much does it cost to rent a home in Chester, NY?
The median rent for a home in Chester, NY is $3,275 per month, though prices vary by neighborhood, size, and property type. As of August 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 $131,000 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 $3,275 per month in Chester, NY, renters typically need to show $9,825 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 12.7, 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 Home Trends

Number of Homes for Rent
10
Median Rent
$3,275
Median Single Family Home Rent
$2,650
Median Townhouse Rent
$2,550
Median Condo Rent
$1,750
How to Rent a Home