13

Newest Homes for Rent in Chester, NY

Section Image Section Image
  • /7

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft
    • Property for Rent

    222 Lehigh Ave, Chester, NY 10918

    Charming. Updated. Affordable.Welcome to this beautifully updated 2-bedroom, 1-full bath trailer, offering comfortable living with modern finishes throughout. Step inside to a bright, open living area designed for both relaxing and entertaining.The stunning white kitchen features elegant quartz countertops with quartz backsplash, beautiful cabinetry, and plenty of workspace, creating

    Roxanne Hartman Timothy W. Kramer

    222 Lehigh Ave, Chester, NY 10918
  • /6

    $1,600 Per Month

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

    8 Main St Unit 1, Chester, NY 10918

    Located in Historic Downtown Chester. This is a 1 bedroom apartment located on the 2nd floor. New kitchen and flooring throughout. Open floor plan with exposed brick walls and lots of natural light. Access to a backyard area. 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 Unit 1, Chester, NY 10918
  • /21

    $3,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    580 Lakes Rd, Monroe, NY 10950

    LAKE VIEWS FROM BALCONY!!! LAKE RIGHTS! With lake access and a deck on the lake. Check out this 3 Bedroom, 2 bathroom Two Story style home nestled in the Village of Monroe and directly across the street from Walton Lake, located in the Monroe-Woodbury School District and within a short drive to local restaurants, shopping, parks and most major highways. If the location isn't enough then check out

    Moses Schreiber MS Realty Group USA, Inc

    580 Lakes Rd, Monroe, NY 10950
  • /12

    $2,100 Per Month

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

    53 Main St Unit 4, Chester, NY 10918

    Property Id: 2791335 Welcome to your new home at 53 Main St in Chester, NY! This single unit offers modern amenities including oven, microwave, washer, dryer, and more. Enjoy the convenience of off-street parking, security cameras, and a secure building. No pets allowed. Rent for $2100/month starting 09/01/2026. Don't miss out on this fantastic opportunity! No Smoking ,credit and reference

    53 Main St Unit 4, 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
  • /14

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 1,784 Sq Ft
    • House for Rent

    649 Lakes Rd, Monroe, NY 10950

    Escape to this adorable, quaint 1 bedroom stone cottage in the heart of Monroe, just minutes from the Village, local shops, restaurants, and the scenic Millponds. This fully furnished one-bedroom rental offers flexible lease terms and a bright, welcoming layout filled with natural light. The spacious bedroom and living room showcases beautiful natural wood walls, creating warmth and character,

    Sandra Spector Howard Hanna Rand Realty

    649 Lakes Rd, Monroe, NY 10950
  • /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
  • /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
  • /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
  • /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

    $3,275 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
  • /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
  • /89

    $16,143

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $16,143/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

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 $2,300 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 $92,000 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 $2,300 per month in Chester, NY, renters typically need to show $6,900 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 18.1, 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
13
Median Rent
$2,300
Median Single Family Home Rent
$2,600
Median Townhouse Rent
$2,520
Median Condo Rent
$2,000
How to Rent a Home