10

Pawling, NY Homes for Sale with Garage

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  • /42

    $598,500

    • 4 Beds
    • 4.5 Baths
    • 2,361 Sq Ft

    126 Old Route 55, Pawling, NY 12564

    Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, Pawling, NY 12564
  • /48

    $1,200,000

    • 5 Beds
    • 4 Baths
    • 4,248 Sq Ft

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 415-7723

    64 S Quaker Hill Rd, Pawling, NY 12564
  • /15

    $975,000

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    14 Akindale Rd, Pawling, NY 12564

    TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better place

    Kathryn McCoach Houlihan Lawrence Inc.

    14 Akindale Rd, Pawling, NY 12564
  • /47

    $1,175,000

    • 4 Beds
    • 6 Baths
    • 3,012 Sq Ft

    16 Anderson Rd, Pawling, NY 12564

    Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

    Ryan Arket Compass Greater NY, LLC

    16 Anderson Rd, Pawling, NY 12564
  • /50

    $619,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    322 Old Route 22, Pawling, NY 12564

    Welcome to 322 Old Route 22! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families. Great location just a few minutes from the heart of the Village of Pawling! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside,

    Susan Stevens BHHS Hudson Valley Properties

    322 Old Route 22, Pawling, NY 12564
  • /15

    $1,250,000

    • 4 Beds
    • 4.5 Baths
    • 3,200 Sq Ft

    120 Harmony Rd, Pawling, NY 12564

    New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

    Bliss Voutsinas Hillside Realty & Development

    120 Harmony Rd, Pawling, NY 12564
  • /13

    $408,888

    • 3 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    21 Kings Way, Pawling, NY 12564

    Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderful community in Pawling, NY. This beautifully maintained home offers a perfect blend of comfort, style, and convenience. Step inside to discover an inviting open floor plan with spacious living areas, perfect for both entertaining and everyday living. The large windows flood the space with natural light,

    Bopaul Sookdeo YourHomeSold Guaranteed Realty

    21 Kings Way, Pawling, NY 12564
  • /46

    $39,000,000

    • 9 Beds
    • 15 Baths
    • 55,000 Sq Ft

    104 N Garden Dr, Pawling, NY 12564

    Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same family has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings,

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    104 N Garden Dr, Pawling, NY 12564
  • /50

    $479,900

    • 3 Beds
    • 3.5 Baths
    • 3,467 Sq Ft

    2 Bridle Way, Pawling, NY 12564

    Welcome to 2 Bridle Way, a rare opportunity to own a spacious 3-bedroom, 3.5-bath Colonial in one of Pawling’s most desirable and well-kept communities. Built in 1992, this young home offers an impressive layout with generous room sizes, abundant natural light, and endless potential for the next owner to bring their vision to life. Located in a sought-after HOA neighborhood, residents enjoy the

    Arafat Ibrahim AI Realty Brokerage LLC

    2 Bridle Way, Pawling, NY 12564
  • /36

    $5,500,000

    • 17 Beds
    • 13 Baths
    • 15,000 Sq Ft

    618 Quaker Hill Rd, Pawling, NY 12564

    25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

    Harriet Norris Douglas Elliman Real Estate

    618 Quaker Hill Rd, Pawling, NY 12564

Home Trends in Pawling, NY

Housing Trends

Median Sale Price
$537,500
Median Single Family Sale Price
$603,500
Median Townhouse Sale Price
$370,750
Median 2 Bedroom Sale Price
$361,000
Average Price Per Sq Ft
$271
Number of Homes for Sale
12
Last 12 months Home Sales
68
Months of Supply
2.10
Median List Price
$552,500
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
3%
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