13

4-Bedroom Homes for Sale in Pawling, NY

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  • /42

    $599,000

    • 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

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

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

    $749,000

    • 4 Beds
    • 3 Baths
    • 3,360 Sq Ft

    94 S Quaker Hill Rd, Pawling, NY 12564

    Set on 3.62 acres of picturesque and private land, this expansive 4-bedroom split-level home offers the perfect balance of spacious living and resort-style outdoor amenities, highlighted by a 20’ x 50’ saltwater in-ground pool. As you arrive along the freshly paved driveway, you’ll feel instantly at home in your own private oasis. Inside, a bright foyer with gleaming hardwood floors leads to the

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 253-5932

    94 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

    Kathryn McCoach Houlihan Lawrence Inc.

    14 Akindale Rd, Pawling, NY 12564
  • /47

    $1,250,000

    • 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
  • /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

    120 Harmony Rd, Pawling, NY 12564
  • /29

    $749,000

    • 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
  • /34

    $699,000

    • 4 Beds
    • 5 Baths
    • 4,199 Sq Ft

    29 Cunningham Ln, Pawling, NY 12564

    Harmony Woods, an enclave of beautiful homes on the outskirts of the Village. This contemporary home has so much living space. Meticulously & continuously maintained by the current owners, there is nothing to be done! The 2 story foyer w/tile floors leads to the sunken LR which has high ceilings, a 2 sided fireplace, large windows & w/w carpet. There is formal DR, 2 powder rooms, then on to the

    Gillian Stewart Gillian Stewart Real Estate

    29 Cunningham Ln, Pawling, NY 12564
  • /37

    $699,000

    • 4 Beds
    • 5 Baths
    • 4,018 Sq Ft

    175 Old Quaker Hill Rd, Pawling, NY 12564

    A Stately Cape Cod Estate with exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

    Tom Consaga RE/MAX Ace Realty

    175 Old Quaker Hill Rd, Pawling, NY 12564
  • /22

    $859,000

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

    26 Rodina Dr, Pawling, NY 12564

    Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. 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 with motion sensor lighting on

    Douglas Servello Home Sweet Home Properties

    26 Rodina Dr, Pawling, NY 12564
  • /43

    $734,900 Open Sun 12PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,283 Sq Ft

    27 Millstream Ct, Pawling, NY 12564

    FULLY AVAILABLE. BUYER WAS UNABLE TO SECURE FINANCING (10/6/25). These remarks will be updated daily. Welcome to your new home in the neighborhood you want and with all the amenities you want. Imagine waking in your Oversized Primary bedroom to the sounds of birds chirping and the sun warming your face. Get the day going in your Primary Bath Suite with Double Vanity, Heated Floors, Heated Towel

    Christopher Filangeri BHHS Hudson Valley Properties

    27 Millstream Ct, Pawling, NY 12564
  • /36

    $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, Grand Prix polo field, over 100 acres of fenced property, and 150 acres of riding trails

    Brian McGrath McGrath Realty Inc

    15 Kirby Hill Rd, Pawling, NY 12564
  • /23

    $1,445,000

    • 4 Beds
    • 3.5 Baths
    • 4,178 Sq Ft

    29 Marble Ln, Pawling, NY 12564

    Fully Approved Shovel Ready Fabulous ultra private 5 plus acre homesite in a deed restricted, eco-sensitive subdivision. Don't miss the opportunity to have your dream home built by an experienced local builder. Once built, this spacious front porch colonial will be enhanced by light infused rooms, an open floor plan and custom eat in kitchen perfect for preparing scrumptious meals. A family room

    John Ravetto Houlihan Lawrence Inc.

    29 Marble Ln, Pawling, NY 12564
  • /37

    $775,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,611 Sq Ft

    4 Mane Way, Pawling, NY 12564

    Elegant and Updated Center Hall Colonial, ideally situated in The Highlands—a beautiful and highly sought-after neighborhood in the charming Town of Pawling. This spacious four-bedroom, two-and-a-half-bath home seamlessly blends timeless architectural character with modern luxury, offering comfort, style, and functionality for today’s lifestyle. Gleaming hardwood floors flow throughout the main

    Sharon Sheil Coldwell Banker Realty

    4 Mane Way, Pawling, NY 12564

Home Trends in Pawling, NY

Housing Trends

Median Sale Price
$533,500
Median Single Family Sale Price
$610,000
Median Townhouse Sale Price
$361,000
Median 2 Bedroom Sale Price
$361,000
Average Price Per Sq Ft
$311
Number of Homes for Sale
29
Last 12 months Home Sales
68
Months of Supply
5.10
Median List Price
$597,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
3%
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