14

Newest Homes for Rent in Chester, NY

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  • /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

    $2,450 Per Month

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • House for Rent

    27 Chester St, Monroe, NY 10950

    AMAZING LOCATION!!! LARGE YARD!!! CLOSE TO EVERYTHING!!! Check out this 3 Bedroom, 2 Bathroom house , Updated eat-in kitchen. Large, updated bathroom. Spacious primary bedroom,pull stairs to the attic which can be expanded to add to your living space,within a close proximity to local eateries/restaurants, local shopping, schools,pull stairs to the attic which can be expanded to add to your living

    Nathan Landau Loop Realty Inc

    27 Chester St, Monroe, NY 10950
  • /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
  • /14

    $2,950 Per Month

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

    3410 Whispering Hills, Chester, NY 10918

    Welcome to this charming apartment 3410 Whispering Hills. In this apartment, you will find just about everything you need. Nice kitchen with granite countertops and sunny windows, large dining room with a cozy fireplace, central air condition, 3 nice bedrooms, 3 baths, community pool, and tennis court. this apartment is a corner unit, and it's beautiful. come take a look at this beautiful

    Mordechai Ungar HFA Realty Group

    3410 Whispering Hills, Chester, NY 10918
  • /45

    $2,490 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft
    • Townhouse for Rent

    1208 Whispering Hills, Chester, NY 10918

    Super Clean & Bright Rental in Whispering Hills. 2 Bedrooms, 1.5 Baths, 1 Car Garage with Central Air, Young Kitchen and Appliances, Laminate Flooring on 1st Floor with Laundry and updated Half Bath. Freshly Painted in 2022. Upstairs you will find Primary Bedroom with Vaulted Ceilings, Walk in Closet w/Organizers, Updated Full Bath, Skylight and Spacious Guest Room. Upstairs offers Carpeting.

    Rosalie Cook Weichert Realtors

    1208 Whispering Hills, Chester, NY 10918
  • /6

    $2,100 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
  • /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
  • /28

    $2,800 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
  • /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
  • /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
  • /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

    $3,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Apartment for Rent

    408 Bull Mill Rd Unit 2, Chester, NY 10918

    ***Rare opportunity***Available April 1st for occupancy! Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms,

    Robert Addon Keller Williams Realty

    408 Bull Mill Rd Unit 2, Chester, NY 10918
  • /20

    $16,120

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $16,120/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 17, 2026.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

    (845) 599-0724

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
  • /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

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 $3,400 per month, though prices vary by neighborhood, size, and property type. As of May 2026, condos tend to be the most affordable option while single-family homes and townhouses 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 $136,000 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 $3,400 per month in Chester, NY, renters typically need to show $10,200 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 Home Trends in Chester, NY

Rental Home Trends

Number of Homes for Rent
14
Median Rent
$3,400
Median Single Family Home Rent
$2,500
Median Townhouse Rent
$2,550
Median Condo Rent
$1,700
How to Rent a Home