5

Chester, NY Condos 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
  • /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
  • /5

    $3,350 Per Month

    • 4 Beds
    • 3 Baths
    • 1,134 Sq Ft
    • Condo for Rent

    616 Lakes Rd, Monroe, NY 10950

    Beautifully and freshly redone. Has amazing water views from both floors windows!!!

    616 Lakes Rd, Monroe, NY 10950
  • /6

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 1,316 Sq Ft
    • Condo for Rent

    3102 Whispering Hills Unit 678, Chester, NY 10918

    CURRENT TENANTE IS SEEKING A ROOMMATE. Looking to rent a fully furnished 1 bedroom 1 bath. This is within the 3 bedroom unit and common area/kitchen will be shared with the owner. This is a fully air conditioned unit. This would be a month-to-month tenancy and owner is very flexible. Assigned parking spot is available with access to the swimming pool, common area and gym. Located in Chester, NY

    Stephanie Landeck BHG Real Estate Green Team

    3102 Whispering Hills Unit 678, Chester, NY 10918
  • /89

    $16,124

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $16,125/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

Frequently Asked Questions

How much does it cost to rent a condo in Chester, NY?
The median rent for a condo in Chester, NY is $1,950 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 Condos for Rent
5
Median Condo Rent
$1,950
Median 1 Bedroom Condo Rent
$1,650
Median 2 Bedroom Condo Rent
$2,100
Median 3 Bedroom Condo Rent
$2,825
How to Rent a Home