6

Chester, NY Houses for Rent

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  • 20 Goshen Rd, Chester, NY 10918
    20 Goshen Rd, Chester, NY 10918
    20 Goshen 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
  • 208 Glenmere Rd, Chester, NY 10918
    208 Glenmere Rd, Chester, NY 10918
    208 Glenmere Rd, Chester, NY 10918
    /11

    $3,400 Per Month

    • 5 Beds
    • 2.5 Baths
    • 1,815 Sq Ft
    • House for Rent

    208 Glenmere Rd, Chester, NY 10918

    A charming country cottage is available for rent and is situated on a picturesque country road. The main level features an eat-in kitchen, dining room, and two bedrooms, while the upper level has three bedrooms. The cottage boasts updated flooring, windows, kitchen, and heating. The interior has been freshly painted, and new appliances and flooring have been added in 2021. The older "Hamptons"

    208 Glenmere Rd, Chester, NY 10918
  • 66 Murray Dr, Chester, NY 10918
    66 Murray Dr, Chester, NY 10918
    66 Murray Dr, 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
  • 4 Ayr Rd, Chester, NY 10918
    4 Ayr Rd, Chester, NY 10918
    4 Ayr Rd, Chester, NY 10918
    /35

    $4,300 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,968 Sq Ft
    • House for Rent

    4 Ayr Rd, Chester, NY 10918

    Welcome to 4 Ayr Court in Chester, NY — a spacious and beautifully maintained 6-bedroom, 4-bathroom home available for rent! Nestled on a quiet street, this impressive property offers the perfect blend of space, comfort, and convenience. Step inside to find a bright and inviting interior featuring generous living areas, ideal for both everyday living and entertaining. The expansive layout

    Danielle Riggs Keller Williams Hudson Valley

    4 Ayr Rd, Chester, NY 10918
  • 98 Main St, Chester, NY 10918
    98 Main St, Chester, NY 10918
    98 Main St, Chester, NY 10918
    /32

    $2,800 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
  • 60 Evan Rd, Warwick, NY 10990
    60 Evan Rd, Warwick, NY 10990
    60 Evan Rd, Warwick, NY 10990
    /28

    $2,900 Per Month

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

    60 Evan Rd, Warwick, NY 10990

    Please check this well maintained, clean and great size townhouse! It is nestled in the heart of Orange County with Warwick school district. This beautiful home is offering 3 bedrooms, 2 1/2 bathrooms, one car garage and a partial finished basement great for your additional room or for storage. It is an easy commute to major highways, shopping and restaurants. You will enjoy the spacious living

    Anita S. Cristiano HomeSmart Homes & Estates

    60 Evan Rd, Warwick, NY 10990
New York Orange County Chester

Houses for Rent in Chester, NY

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 May 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 $127,000 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 $3,175 per month in Chester, NY, renters typically need to show $9,525 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 13.2, 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 in Chester, NY

There are currently 6 single-family homes available for rent in Chester, NY. The median rent is $2,600 per month, with 3-bedroom houses renting at $3,150, 4-bedroom houses at $3,800 and 5-bedroom houses at $3,400.

Rental Home Trends

Number of Houses for Rent
6
Median Single Family Home Rent
$2,600
Median 3 Bedroom Single Family Home Rent
$3,150
Median 4 Bedroom Single Family Home Rent
$3,800
Median 5 Bedroom Single Family Home Rent
$3,400
How to Rent a Home

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