14

Chester, NY Homes for Rent

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  • /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
  • /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
  • /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
  • /20

    $15,842

    Total Monthly Price

    • 7 Beds
    • 5.5 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $15,843/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 be

    45 Conklingtown Rd Unit SI ID1466647P, 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
  • /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. 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 checked .proof of income. Heat and

    53 Main St Unit 4, 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
  • /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
  • /18

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • Townhouse for Rent

    402 Mountain Laurel Dr, Monroe, NY 10950

    Waterfront living at its finest! HEAT and HOT WATER Included. Welcome to this beautifully maintained center-unit townhome in one of Monroe's most sought-after communities. Offering over 1,800 square feet of living space, this home features 3 bedrooms, 2 full bathrooms, 1 half bath, and breathtaking lake views right from your backyard. The updated eat-in kitchen is the heart of the home,

    Alexandria Sarki Keller Williams Realty

    402 Mountain Laurel Dr, Monroe, NY 10950
  • /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 highways, this surprising end-unit townhome offers exceptional private outdoor space with expansive decking and both large back and side yards with jaw dropping mountain views. A sunny open floor plan with a

    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

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

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 $3,250 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 $130,000 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 $3,250 per month in Chester, NY, renters typically need to show $9,750 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 13.1, 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
14
Median Rent
$3,250
Median Single Family Home Rent
$2,600
Median Townhouse Rent
$2,550
Median Condo Rent
$2,000
How to Rent a Home