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Pawling, NY Homes for Rent

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  • /11

    $1,400 per month

    • 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
  • /40

    $5,000 per month

    • 4 Beds
    • 3 Baths
    • 3,664 Sq Ft
    • House for Rent

    159 Old Quaker Hill Rd, Pawling, NY 12564

    Stunning views to the west can't be beat, this 10.83 acre Ranch style home with 4 bedrooms, 3 full bathrooms (2 en suite) has been completely renovated from top to bottom. There is a stunning chef's kitchen with Silestone counters, stainless appliances & views for days outside the picture window. There is a spectacular great room with wall to ceiling wraparound windows which absorb the view & the

    Gillian Stewart Gillian Stewart Real Estate

    159 Old Quaker Hill Rd, Pawling, NY 12564
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    $2,000 per month

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

    23 E Main St Unit 3B, Pawling, NY 12564

    Now leasing, a one bedroom apartment in a premier rental residence located in the heart of Pawling. Styled in the character of Pawling’s iconic Dutcher House & newly completed, it offers a unique opportunity to live in sophisticated elegance with fine finishing & details throughout. The theme is modern luxury set in a quaint upstate, bucolic 18th century village. The 3rd floor apartment boasts an

    Claudia Jiskra McGrath Realty Inc

    23 E Main St Unit 3B, Pawling, NY 12564
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    $2,950 per month

    • 3 Beds
    • 1 Bath
    • 1,186 Sq Ft
    • House for Rent

    112 Charles Colman Blvd, Pawling, NY 12564

    Delightful C1900 Farmhouse Colonial located on the prettiest streets in the Village. Updated, renovated, & designed to perfection. There are period wood flrs, an updated airy kitchen w/quartz counters, open to a country dining area w/sunny bay window & back dr to patio. The large LR runs front to back w/deep windows, lots of light & sliders to the patio. The covered front porch w/vintage millwork

    Gillian Stewart Gillian Stewart Real Estate

    112 Charles Colman Blvd, Pawling, NY 12564
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    $7,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft
    • House for Rent

    15 Kirby Hill Rd, Pawling, NY 12564

    Now for rent is one of Quaker Hill's most prestigious estate homes. The main estate at Kirby Hill Farm is available as seasonal winter, or yearly rental, impeccably furnished and equipped residential rental with an in-ground pool. Set on close to 250 acres and one of the region's finest equestrian facilities. The circa 1860 colonial farmhouse boasts 3,942 square feet. There are two separate

    Brian McGrath McGrath Realty Inc

    15 Kirby 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 neighborhoods in Pawling, NY for renters?
The most popular neighborhood in Pawling, NY for renters is Germantown.
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, 06784, 06812 and 12533.
How to Rent a Home