7

Pawling, NY Homes for Rent

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  • /24

    $1,950 Per Month

    • 2 Beds
    • 1 Bath
    • 818 Sq Ft
    • Apartment for Rent

    129 Charles Colman Blvd Unit A2, Pawling, NY 12564

    At your fingertips! Everything the Village of Pawling has to offer - Metro North, Lakeside Park, shopping, restaurants and services. Clean, affordable, two bedroom second floor apartment with newer windows and lots of extra storage. Good sized Living Room with plenty of sunshine. Eat in Kitchen with maple cabinets, recessed lighting and tile floor makes this fully functional for your cooking

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 668-4575

    129 Charles Colman Blvd Unit A2, Pawling, NY 12564
  • /24

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 690 Sq Ft
    • Apartment for Rent

    25 Fairway Dr Unit 2, Pawling, NY 12564

    Rare Village of Pawling 2 bedroom, second floor apartment. Open concept Living Room allows you to use the space to fit your needs. Remodeled kitchen with luxury vinyl flooring, stainless steel appliances, granite counter tops and white shaker cabinets for lots of storage. Beautiful, weathered wood backsplash adds a designer touch. Updated bathroom with tub/shower enclosure, white vanity and

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 202-4082

    25 Fairway Dr Unit 2, Pawling, NY 12564
  • /37

    $30,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,233 Sq Ft
    • House for Rent

    121 N Quaker Hill Rd, Pawling, NY 12564

    $30k/month summer. Inquire for other terms. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure

    Joseph Lorino Brown Harris Stevens HV LLC

    121 N Quaker Hill Rd, Pawling, NY 12564
  • /24

    $2,900 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,413 Sq Ft
    • House for Rent

    12 Evergreen Way, Pawling, NY 12564

    Welcome to Cedar Valley! Two-story Townhouse features a spacious Living Rm with fireplace and doors to a brick patio. There is also an open Dining Rm Area. The kitchen has a good amount of cabinets and counter-space, and a small dining area. Also on the first floor is a half bath. The second floor offers a Primary Bedroom with walk-in closet and primary bath. The second bedroom also has an

    Lisa Liffland McGrath Realty Inc

    12 Evergreen Way, Pawling, NY 12564
  • /17

    $3,250 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,700 Sq Ft
    • Apartment for Rent

    10 Fenwood Dr Unit B, Pawling, NY 12564

    Bright & Spacious 3-Bedroom Apartment in Private Setting – Close to Train, Shopping & Schools Enjoy privacy and convenience in this light-filled 3-bedroom, 2.5-bath apartment located in a well-maintained three-family home on a quiet, secluded road just off the main thoroughfare. This spacious apartment offers the perfect balance of peaceful living while being minutes from shopping centers,

    Clayton Livingston McGrath Premier Real Estate

    10 Fenwood Dr Unit B, Pawling, NY 12564
  • /8

    $2,000 Per Month

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

    10 Fenwood Dr Unit C, Pawling, NY 12564

    Charming and spacious 2-bedroom, 1-bath apartment featuring high ceilings, skylights, and ceramic tile floors throughout, creating a bright and open living environment. This inviting home offers a private entry, providing added privacy and convenience. The apartment is filled with natural light thanks to the skylights and generous ceiling height, giving the living spaces an airy and comfortable

    Clayton Livingston McGrath Premier Real Estate

    10 Fenwood Dr Unit C, Pawling, NY 12564

Why Live in Pawling

Pawling, NY, spans 45 square miles in Dutchess County, offering residents a blend of rural solitude and accessibility to New York City via an MTA station for an hour-long commute. The town features over 1,000 acres of protected parklands, including the Pawling Nature Reserve, where locals can hike the Appalachian Trail. Recreational options also include Dutcher Golf Course and Whaley Lake, the largest lake in the county, ideal for swimming, kayaking, and fishing. The Maybrook Trailway, part of the Empire State Trail system, provides scenic hiking opportunities. Pawling's housing market includes upscale single-family homes such as Colonial Revivals, ramblers, raised ranches, and split-levels, with exclusive areas like Quaker Hill offering large farms and multimillion-dollar properties. The central village features Craftsman and Victorian homes, while waterfront cottages are available in Holmes. Pawling Central School District serves the community with highly rated schools, including Pawling Elementary, Pawling Middle, and Pawling High. The private Trinity-Pawling School, an all-boys Episcopal boarding school, is also highly rated. Local amenities include grocery stores like Acme Markets and Hannaford along NY-22, and dining options such as O’Connor’s Public House downtown. Community traditions include the Pawling Farmers Market and the Pawling Concert Series, along with Decemberfest and Tree Lighting events. Commuters can reach Manhattan in an hour and a half by train or car, and New Haven, Connecticut, is accessible within two hours.

Frequently Asked Questions

How much does it cost to rent a home in Pawling, NY?
The median rent for a home in Pawling, NY is $2,000 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 Pawling, NY?
To comfortably afford the median rent in Pawling, NY, a household needs to earn roughly $80,000 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 $2,000 per month in Pawling, NY, renters typically need to show $6,000 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 Pawling, NY?
In Pawling, NY, the price-to-rent ratio is 20.3, 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 Pawling, NY

Rental Home Trends

Number of Homes for Rent
7
Median Rent
$2,000
Median Single Family Home Rent
$3,250
Median Townhouse Rent
$2,938
Median Condo Rent
$2,708
How to Rent a Home