9

Chester, NY Houses for Rent

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  • /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
  • /11

    $3,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • House for Rent

    13 Maple Ln, Monroe, NY 10950

    Property Id: 2842725 Piso/nivel superior en alquiler: 3 habitaciones 1 baño completo 1 cocina completa acceso al deck acceso a lavandería estacionamiento para 2 vehículos Precio: $3,000.00 con bills incluido Price: 3,000.00 with bills included top floor/level for rent: 3 bedrooms 1 full bathroom 1 full kitchen

    13 Maple Ln, Monroe, NY 10950
  • /6

    $1,800 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    33 Schnabel Rd, Chester, NY 10918

    Property Id: 2620401 One bedroom and one living room with private entrance private bathroom and Landry room and parking space

    33 Schnabel 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
  • /27

    $3,250 Per Month

    • 4 Beds
    • 1 Bath
    • 2,277 Sq Ft
    • House for Rent

    7 Ruscitti Dr, Chester, NY 10918

    Welcome to your spacious new home at 7 Ruscitti Drive in charming Chester, NY! This bright and airy single-family home features 4 generous bedrooms, a full bath, and a large basement with plenty of extra storage space, giving everyone room to relax, work, or stay organized. Best of all, pets are warmly welcomed! Located in a quiet, friendly neighborhood in the heart of the Hudson Valley, you’ll

    Abraham Schwartz Priority Management

    7 Ruscitti Dr, Chester, NY 10918
  • /36

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,630 Sq Ft
    • House for Rent

    21 Darin Rd, Warwick, NY 10990

    THE VIEWS, THE LIFESTYLE, THE SPACE all in one beautiful townhouse located in an award winning school district. Just five minutes to the Village of Warwick and easy access to major highway, this surprising end-unit townhome offers exceptional outdoor space with expansive decking and private large back and side yard with jaw dropping mountain views. A sunny open floor plan with a contemporary

    Amy Wilhelm Corcoran Baer & McIntosh

    21 Darin Rd, Warwick, NY 10990
  • /24

    $2,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,920 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
  • /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
  • /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

Frequently Asked Questions

How much does it cost to rent a single-family home in Chester, NY?
The median rent for a single-family home in Chester, NY is $2,600 per month, though prices vary by neighborhood, size, and property type. As of September 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 $111,000 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 $2,775 per month in Chester, NY, renters typically need to show $8,325 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 15.5, 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 Houses for Rent
9
Median Single Family Home Rent
$2,600
Median 3 Bedroom Single Family Home Rent
$3,500
Median 4 Bedroom Single Family Home Rent
$3,450
How to Rent a Home