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Colonial Homes for Sale in Pawling, NY

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  • /38

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    128 Old Pawling Rd, Pawling, NY 12564

    Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features

    Agent Photo

    Teddie Leonaggeo

    McGrath Realty Inc

    128 Old Pawling Rd, Pawling, NY 12564
  • /49

    $639,000

    • 4 Beds
    • 3.5 Baths
    • 1,696 Sq Ft

    3846 Route 55, Pawling, NY 12564

    Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow.The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood

    Agent Photo

    Leigh Tripathi

    Ellis Sotheby's Intl Realty

    3846 Route 55, Pawling, NY 12564
  • /30

    $645,000

    $54K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,724 Sq Ft

    3120 Route 55, Pawling, NY 12564

    Attention Nature Lovers - This property is nestled on 3.37 picturesque, partially wooded acres and the Appalachian Trail literally crosses State Route 55 (at the border of Poughquag and Pawling, NY), putting a stretch of the trail within walking distance, east of the residence (across Rt. 55). This beautifully maintained 3-bedroom, 3.5-bath residence offers an exceptional blend of privacy,

    Erika Johnson Keller Williams Realty Partner

    3120 Route 55, Pawling, NY 12564
  • /45

    $600,000

    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    5 Red Tail Ct, Pawling, NY 12564

    Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space.

    Susan Salamone Houlihan Lawrence Inc.

    5 Red Tail Ct, Pawling, NY 12564
  • /5

    $1,400,000

    • 4 Beds
    • 2.5 Baths
    • 4,136 Sq Ft

    392 Old Quaker Hill Rd, Pawling, NY 12564

    Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.

    Joseph Sala McGrath Realty Inc

    392 Old Quaker Hill Rd, Pawling, NY 12564
  • /46

    $1,799,000

    • 5 Beds
    • 5.5 Baths
    • 5,390 Sq Ft

    41 and 43 Meeting House Rd, Pawling, NY 12564

    A Quintessential Quaker Hill Estate with Guest CottagePerched atop the storied hills of Quaker Hill, this exceptional five-acre estate embodies the romance and elegance of country living at its finest. Privately nestled amid sweeping meadows, renowned equestrian properties, and grand country estates, 43 Meeting House Road offers a rare combination of exclusivity, beauty, and refined

    Richard Esman Douglas Elliman Real Estate

    41 and 43 Meeting House Rd, Pawling, NY 12564
  • /37

    $14,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft

    15 Kirby Hill Rd, Pawling, NY 12564

    Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

    Brian McGrath McGrath Realty Inc

    15 Kirby Hill Rd, Pawling, NY 12564
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