26

Pawling, NY Houses for Sale

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  • /29

    $599,900

    • 2 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    36 Byrds Hill Rd, Pawling, NY 12564

    The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 630-1049

    36 Byrds Hill Rd, Pawling, NY 12564
  • /42

    $599,000

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

    126 Old Route 55, Pawling, NY 12564

    This charming, expansive ranch home is thoughtfully designed to suit a variety of living arrangements, whether for a large family, extended family, or a mother-daughter setup. With 4-5 bedrooms and 4 full bathrooms (3 of which are en suite), this home offers both space and privacy for everyone.The kitchen is a chef's dream, featuring elegant soapstone countertops, a copper sink, and

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

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

    $799,999

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

    94 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities including a 20 x 50 salt water inground pool. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 622-7595

    94 S Quaker Hill Rd, Pawling, NY 12564
  • /29

    $889,000

    • 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
  • /47

    $1,300,000

    • 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
  • /47

    $1,485,000

    • 5 Beds
    • 7.5 Baths
    • 5,470 Sq Ft

    604 N Quaker Hill Rd, Pawling, NY 12564

    Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the

    Leigh Tripathi Ellis Sotheby's Intl Realty

    604 N Quaker Hill Rd, Pawling, NY 12564
  • /48

    $799,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /33

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 3,035 Sq Ft

    6 Byrds Hill Rd, Pawling, NY 12564

    Modern Pawling Farmhouse - This beautifully renovated Colonial home near Scenic Quaker Hill offers a perfect blend of charm and modern amenities. The spacious kitchen, complete with a center island with seating, flows seamlessly into an open dining and living area, where a cozy fireplace awaits. A separate light-filled den provides a peaceful retreat for relaxation. The main floor features a

    Stephen Pener William Pitt Sothebys Int Rlty

    6 Byrds Hill 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
  • /50

    $1,500,000

    • 4 Beds
    • 3.5 Baths
    • 4,683 Sq Ft

    21 Brady Brook Farm Rd, Pawling, NY 12564

    Nestled within the prestigious Brady Brook Falls subdivision on sought-after Quaker Hill, this exquisite colonial offers an unparalleled blend of elegance, privacy, and modern convenience. Situated at the end of a serene cul-de-sac, the home is surrounded by picturesque horse farms and country estates. A long, private driveway leads to this stunning 6.65-acre retreat, complete with a heated

    Brian McGrath McGrath Realty Inc

    21 Brady Brook Farm Rd, Pawling, NY 12564
  • /47

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,706 Sq Ft

    14 Summit Ave, Pawling, NY 12564

    Tucked away on a quiet dead-end street in the serene village of Pawling, this meticulously maintained Cape Cod home offers the perfect blend of comfort, charm, and convenience. Bathed in natural light, the freshly painted interior boasts a seamless flow between living spaces, with two spacious bedrooms that live like three—ideal for guests, a home office, or flexible living. The inviting living

    Karen Gundelach Keller Williams Realty Partner

    14 Summit Ave, Pawling, NY 12564
  • /34

    $650,000

    • 3 Beds
    • 3 Baths
    • 1,450 Sq Ft

    54 Nanny Hill Rd, Pawling, NY 12564

    This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

    Kaye Saglibene

    54 Nanny Hill Rd, Pawling, NY 12564
  • /47

    $749,900

    • 3 Beds
    • 2 Baths
    • 2,107 Sq Ft

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

    Mark Snyder eXp Realty

    28 Gobblers Knob Rd, Pawling, NY 12564
  • /28

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,152 Sq Ft

    42 Harmony Rd, Pawling, NY 12564

    Located on one of Pawling's most charming country roads, while still within a five-minute drive from the quaint and lively village center, this salt-box style home is awaiting your creativity and love. With a cozy and convenient fireplace in the living room, and a front-porch that overlooks an idyllic forest and beaver-pond across the street, the property feels isolated and quiet while still

    Reid McGrath McGrath Realty Inc

    42 Harmony Rd, Pawling, NY 12564
  • /24

    $499,000

    • 5 Beds
    • 1,062 Sq Ft

    215 Little Pond Rd, Pawling, NY 12564

    Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and peaceful environment.

    Jillian Pajer Douglas Elliman Real Estate

    215 Little Pond Rd, Pawling, NY 12564
  • /43

    $734,900

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

    27 Millstream Ct, Pawling, NY 12564

    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 Rack and Jacuzzi Tub. Smell the coffee brewing in your Chef's kitchen where you can prepare meals that

    CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

    27 Millstream Ct, Pawling, NY 12564
  • /37

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft

    36 Elm St, Pawling, NY 12564

    A historic Village Colonial on a quiet street, is a delight to show. Immaculate, well maintained & updated. Downstairs, a formal living room with a gas stove fireplace & bay windows, a formal dining room with built ins for storage, an office with closets & shelves for storage, a foyer, hardwood floors, a stunning eat in chef's kitchen with stone counters, stainless appliances, a big closet &

    Gillian Stewart Gillian Stewart Real Estate

    36 Elm St, Pawling, NY 12564
  • /50

    $5,199,000

    • 8 Beds
    • 11 Baths
    • 11,301 Sq Ft

    955 Old Quaker Hill Rd, Pawling, NY 12564

    Perched atop historic Quaker Hill, MAIN TOP, is a private oasis of 20 gated acres with a stately manor, heated saltwater pool, tennis court, and endless mountain vistas that reach across 5 states. The 11,301 sq. ft. residence blends timeless elegance with high ceilings, oak floors, and fine details. Inside, you’ll find stunning formal rooms including a dramatic 47 ft living room, an entertaining

    Gladys Disisto Christie's Int. Real Estate

    955 Old Quaker Hill Rd, Pawling, NY 12564
  • /50

    $720,000

    • 4 Beds
    • 4.5 Baths
    • 2,920 Sq Ft

    12 W Wind Rd, Pawling, NY 12564

    Nestled on over two serene acres and backing to a tranquil nature preserve, this beautifully maintained home offers the perfect blend of peace, privacy, and natural beauty. With breathtaking seasonal views of the surrounding woodlands, the setting is ideal for quiet reflection or lively gatherings.Though the tax card shows four-bedrooms, this spacious home lives like a five-bedroom,

    Doris Jean William Raveis Real Estate

    12 W Wind Rd, Pawling, NY 12564
  • /38

    $699,000

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

    5 Red Tail Ct, Pawling, NY 12564

    Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy fireplace, a

    Julius Cooper eXp Realty

    5 Red Tail Ct, Pawling, NY 12564
  • /9

    $1,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    51 Estate Dr, Pawling, NY 12564

    Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

    Tony Zaccardo Coldwell Banker Realty

    51 Estate Dr, Pawling, NY 12564
  • /2

    $650,000

    • 6 Beds
    • 2 Baths
    • 2,856 Sq Ft

    13 Rebecca Dr, Pawling, NY 12564

    This Ranch home offers 6 bedrooms and 2 full baths. There is 2,856 sqft of living space above the walk-out basement. Home is currently being used as a Residential Facility and will be held as a Rental with existing Residents in the home until DECEMBER 2026. This is a unique situation where the home can be held as an Invesment until 2026 and thereafter utilized by the new owner. Generator

    Angela Briante Briante Realty Group, LLC

    13 Rebecca Dr, 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
  • /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
  • /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
  • /42

    $539,900

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

    2 Bridle Way, Pawling, NY 12564

    Wonderful investment opportunity awaits with this spacious home. The inviting library-style living room showcases nicely finished built-ins, while the expansive kitchen with a dining area seamlessly flows into the family room, highlighted by a cozy fireplace. The primary suite includes a private bathroom, ensuring comfort and convenience. A finished walkout lower level expands the living space

    Jonathan Gineo Jonathan D. Gineo

    2 Bridle Way, Pawling, NY 12564

Why Live in Pawling

Pawling is a rural neighborhood in Dutchess County, known for its expansive green spaces and convenient commute to New York City. Spanning 45 square miles, Pawling offers residents over 1,000 acres of protected parklands and an MTA station for a commute to the city in about an hour and a half. Housing styles include Colonial Revivals, ramblers, raised ranches, and split-levels, with upscale options in Quaker Hill and waterfront cottages in Holmes. Pawling Nature Reserve and Whaley Lake are popular recreational spots, offering hiking, swimming, kayaking, and fishing. The Dutcher Golf Course, the oldest 9-hole municipal course in the country, is another local highlight. For groceries, residents frequent Acme Markets and Hannaford along NY-22, while dining options include O’Connor’s Public House in downtown Pawling. The Pawling Farmers Market and Pawling Concert Series are longstanding community traditions, and the Decemberfest and Tree Lighting event brings neighbors together during the holidays. Education is well-regarded with Pawling Elementary, Pawling Middle, and Pawling High School, alongside the private Trinity-Pawling School. The neighborhood's proximity to major highways also allows for easy access to New Haven, Connecticut, in under two hours.

Home Trends in Pawling, NY

Housing Trends

Median Sale Price
$552,500
Median Single Family Sale Price
$645,000
Median Townhouse Sale Price
$367,750
Median 2 Bedroom Sale Price
$365,000
Average Price Per Sq Ft
$314
Number of Homes for Sale
25
Last 12 months Home Sales
70
Months of Supply
4.30
Median List Price
$600,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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