13

Pawling, NY Homes for Sale with Garage

Section Image Section Image
  • /23

    $799,000

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

    26 Rodina Dr, Pawling, NY 12564

    Be the first to live in this stunning four bedroom, two and a half bath home nestled on a beautiful two and a half acre lot. This home is located on the border of Putnam and Duchess counties. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing staircase with

    Agent Photo

    Douglas Servello

    Home Sweet Home Properties

    (845) 599-8285

    26 Rodina Dr, Pawling, NY 12564
  • /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
  • /50

    $599,000

    • 2 Beds
    • 2 Baths
    • 1,428 Sq Ft

    168 Old Route 55, Pawling, NY 12564

    Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 932-0435

    168 Old Route 55, Pawling, NY 12564
  • /50

    $619,000

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

    322 Old Route 22, Pawling, NY 12564

    Multi-family in Pawling! This spacious, newly remodeled 2-family home is located just a few minutes from the Village of Pawling - a great opportunity for owner-occupants, investors, or extended families! 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, both units are

    Susan Stevens BHHS Hudson Valley Properties

    322 Old Route 22, Pawling, NY 12564
  • /29

    $2,500,000

    • 6 Beds
    • 6.5 Baths
    • 6,625 Sq Ft

    3302 Route 55, Pawling, NY 12564

    Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 private acres with breath taking views. Mother Nature is at her best. Exceptional beauty for all four seasons. The unique and exquisite architectural design of this home lends to expansive living space, tucked behind gated entry. This home offers expansive living space, luxury and customize finishes throughout. A true

    STACI MACKIN Dixon Smith Realty

    3302 Route 55, Pawling, NY 12564
  • /24

    $950,000

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

    128 Old Pawling Rd, Pawling, NY 12564

    Welcome to 128 Old Pawling Road, a beautifully situated property in Pawling, NY. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether

    Juliska Martino Compass Greater NY, LLC

    128 Old Pawling Rd, Pawling, NY 12564
  • /24

    $485,000

    • 3 Beds
    • 3.5 Baths
    • 2,503 Sq Ft

    20 Saratoga St, Pawling, NY 12564

    Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Deerfield Ponds community. Bright, warm, and beautifully maintained, this home offers an ideal blend of comfort, convenience, and modern living. Step inside to an inviting living room that seamlessly flows into the dining area and a charming kitchen with a cozy breakfast nook, all appliances updated within the

    Julia Lear Coldwell Banker Realty

    20 Saratoga St, 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
  • /33

    $889,900

    • 3 Beds
    • 2 Baths
    • 2,048 Sq Ft

    1125 Old Quaker Hill Rd, Pawling, NY 12564

    Tucked away in the prestigious Quaker Hill area of Pawling, this cozy ranch-style country home offers a private setting, on 6.8 wooded acres, where time slows and weekends linger. Thoughtfully renovated in 2018, the residence is rich in character, featuring 100-year-old reclaimed posts and beams from a barn in Western PA and 150-year-old wide-board floors reclaimed from a CT tobacco barn that

    Diana Murphy HomeSmart Homes & Estates

    1125 Old Quaker Hill Rd, Pawling, NY 12564
  • /29

    $705,000

    • 4 Beds
    • 3 Baths
    • 3,888 Sq Ft

    12 Rebecca Dr, Pawling, NY 12564

    Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

    Kevin Sanabria eRealty Advisors, Inc

    12 Rebecca Dr, 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 owner 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, it

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    104 N Garden Dr, Pawling, NY 12564
  • /49

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,567 Sq Ft

    13 Cushing Green S, Pawling, NY 12564

    A rare find and an incredible opportunity awaits in Squire Green with this two-story end-unit townhome featuring the highly sought-after attached garage. Townhomes are seldom available in the Squire Green section of the Deerfield Ponds community, and end units are even more uncommon, making this offering especially desirable. Steps inside reveal a spacious entry foyer leading to an updated

    Claudia Jiskra McGrath Realty Inc

    13 Cushing Green S, Pawling, NY 12564

Home Trends in Pawling, NY

Housing Trends

Median Sale Price
$522,250
Median Single Family Sale Price
$598,750
Median Townhouse Sale Price
$386,000
Median 2 Bedroom Sale Price
$365,000
Average Price Per Sq Ft
$272
Number of Homes for Sale
16
Last 12 months Home Sales
68
Months of Supply
2.80
Median List Price
$545,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home