15

Newest Homes for Rent in Chester, NY

Section Image Section Image
  • /25

    $2,800 Per Month

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

    1390 Kings Hwy, Chester, NY 10918

    Do not miss this 3 bedroom 2 bath rental in the heart of Sugarloaf Village! Close to the restaurants and shops. The bedrooms are large and the home is warm and welcoming. There is a large enclosed front porch as well as a back patio and yard. You will have use of the Garage and driveway. Room for 2 cars. No pets please.

    Christine Koenig Keller Williams Realty

    1390 Kings Hwy, Chester, NY 10918
  • /6

    $1,800 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    33 Schnabel Rd, Chester, NY 10918

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

    33 Schnabel Rd, Chester, NY 10918
  • /33

    $2,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Townhouse for Rent

    1502 Whispering Hills, Chester, NY 10918

    Beautiful 3 bedrooms and 2 baths in Whispering Hills. Updated and freshly painted. New carpeting. Fire place and vaulted ceiling.Enjoy resort style living with pools, tennis courts, club house, gym, playgrounds and basketball courts. Located close to major highways for an easy commute. Additional Information: ParkingFeatures:1 Car Attached,Storage: Garage,

    Nikki Grzegorzewski Keller Williams Realty

    1502 Whispering Hills, Chester, NY 10918
  • /13

    $2,900 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Apartment for Rent

    168 Pine Hill Rd Unit 1, Chester, NY 10918

    RENT INCLUDES ELECTRIC, CENTRAL AC, HEAT & HOT WATER!! Welcome to Unit #1 of 168 Pine Hill Rd. This lovely three bedroom, 1.5 bath apartment offers beautiful views with lots of natural light, an eat in kitchen with stainless steel refrigerator and stove (gas) as well as in unit washer and dryer for added convenience, 3 nice sized bedroom. Easy access- no steps to enter the two level unit. There

    Claudia Lepore Keller Williams Realty

    168 Pine Hill Rd Unit 1, Chester, NY 10918
  • /13

    $2,800 Per Month

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • House for Rent

    27 Midway Dr, Monroe, NY 10950

    Charming Ranch home is waiting for you! Super condition! Beautiful perfectly maintained kitchen, 3 Bedrooms and 1 full bath. Enjoy the secluded deck surrounded with beautiful greenery! This Home has Walton Lake rights! Schedule your tour today!

    Joseph Rosenfeld Flag Realty Group

    27 Midway Dr, Monroe, NY 10950
  • /43

    $3,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Apartment for Rent

    1403 Kings Hwy, Chester, NY 10918

    Luxury Farmhouse Rental in the Heart and Soul of Sugar Loaf – Warwick Schools! Experience country luxury at its finest in this stunning farmhouse rental located in the charming hamlet of Sugar Loaf. Designed for those who appreciate quality craftsmanship and timeless character, this exceptional home offers approximately 3,200 square feet of beautifully appointed living space. Step inside to

    Carla Terranova Keller Williams Realty

    1403 Kings Hwy, Chester, NY 10918
  • /20

    $2,695 Per Month

    • 3 Beds
    • 1 Bath
    • 2,386 Sq Ft
    • Apartment for Rent

    28 Academy Ave Unit 2, Chester, NY 10918

    Available for Rent! Spacious 3-bedroom, 1-bath second-floor apartment located in the heart of Chester. This well-maintained unit features a finished attic, providing additional flexible living space perfect for a home office, playroom, or storage. Conveniently located close to shopping, restaurants, parks, schools, and major commuter routes. Enjoy all that the Village of Chester has to offer

    Agent Photo

    Ammar Iqbal

    eXp Realty

    28 Academy Ave Unit 2, Chester, NY 10918
  • /16

    $2,670 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Townhouse for Rent

    1907 Whispering Hills, Chester, NY 10918

    Welcome home to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. Enjoy a cozy fireplace in your spacious living room, kitchen with tile flooring for easy cleanup, and a patio right outside your front sliding doors for summer night enjoyment after taking a dip in the community pool.

    Erin Hansford Stonewall Realty Group LLC

    1907 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

    $1,950 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

    7 Kennedy Ln Unit 3, Monroe, NY 10950
  • /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
  • /89

    $13,682

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $13,682/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 6, 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 be

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
  • /10

    $2,300 Per Month

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

    82 High St Unit 5, Chester, NY 10918

    NEW CARPET JUST INSTALLED.. 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

    Lynda Hoss Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
  • /7

    $4,000 Per Month

    • 6 Beds
    • 2 Baths
    • House for Rent

    5 Laroc Rd, Chester, NY 10918

    Property Id: 1802590Stunning Home with Expansive Yard and Abundant Storage!Welcome to this incredible property, boasting a massive backyard perfect for outdoor entertaining! Enjoy warm weather gatherings on the spacious deck, and make the most of the two sheds for storing tools, equipment, and more.This fantastic home also features:- 1 garage for secure vehicle

    5 Laroc Rd, 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 $2,900 per month, though prices vary by neighborhood, size, and property type. As of July 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 $116,000 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 $2,900 per month in Chester, NY, renters typically need to show $8,700 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 14.3, 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

Number of Homes for Rent
15
Median Rent
$2,900
Median Single Family Home Rent
$2,800
Median Townhouse Rent
$2,550
Median Condo Rent
$1,900
How to Rent a Home