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Pawling, NY Homes for Rent

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  • /10

    $1,400 total monthly price

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    23 W Main St Unit 1A, Pawling, NY 12564

    Two room studio in the historical Village of Pawling. Ground floor, private entrance. Convenient parking. Walk to Metro-North, shopping, laundry. No smoking/pets Call only

    23 W Main St Unit 1A, Pawling, NY 12564
  • /9

    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    104 E Main St Unit 5, Pawling, NY 12564

    Spacious one bedroom apartment close to the Village of Pawling available for immediate occupancy.

    Bethany Cole HomeSmart Homes & Estates

    104 E Main St Unit 5, 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
  • /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
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    $2,600 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    332 Quaker Hill Rd, Pawling, NY 12564

    Adorable 2 bedroom cottage at the end of a long private drive (which the owner plows!) overlooking 13 acres of open fields alongside an apple orchard. Views for days, covered back porch for those BBQ's & just watching the sun set. Wide wood floors throughout, a fireplace with a wood burning stove insert which heats the whole house (landlord has plenty of wood). The living room is huge with

    Gillian Stewart Gillian Stewart Real Estate

    332 Quaker Hill Rd, 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

What are the most popular zip codes in Pawling, NY for renters?
The most popular zip codes in Pawling, NY for renters include 12564, 12563, 10512, 06812 and 06776.
How to Rent a Home