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Pawling, NY Homes for Rent

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  • /34

    $2,375 per month

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

    134 E Main St, Pawling, NY 12564

    Fully renovated spacious apartment in the Heart of Pawling Village. Everything you see is brand new. Lives like much more than a simple 1-bedroom apartment. Just Minutes to downtown and historic Main Street, this bright and charming unit holds the perfect balance of character and convenience. Situated on the first floor of a classic 1920s Cape Cod-style home, featuring a spacious layout with

    Giancarlo Pecora eXp Realty

    134 E Main St, Pawling, NY 12564
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    $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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    $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
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    $2,650 per month

    • 2 Beds
    • 1 Bath
    • 6,232 Sq Ft
    • Apartment for Rent

    215-217 Old Route 22, Pawling, NY 12564

    Wonderful Bucolic Setting! 2 BR + den - Lovely Cottage on a private estate. Private Garden. Convenient to all.

    Celeste Pasciolla Keller Williams Realty Partner

    215-217 Old Route 22, 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.

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