27

Pawling, NY Homes for Sale

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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
  • /40

    $375,000

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    28 Birch Terrace, Pawling, NY 12564

    Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer.

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    28 Birch Terrace, Pawling, NY 12564
  • /8

    $229,000

    • Land
    • 5.57 Acres
    • $41,113 per Acre

    Lot 21 Cox Rd, Pawling, NY 12564

    Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    Lot 21 Cox Rd, Pawling, NY 12564
  • /43

    $599,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 2,202 Sq Ft

    17 Spring St, Pawling, NY 12564

    Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    17 Spring St, Pawling, NY 12564
  • /44

    $450,000

    • 2 Beds
    • 2 Baths
    • 2,096 Sq Ft

    35 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 35 Gobblers Knob, a charming Contemporary Cape set on 1.67 beautifully landscaped acres. This spacious 2,009 square foot home offers an open and inviting floor plan featuring a bright Living Room, updated Kitchen, and Dining Area perfect for everyday living and entertaining. The Kitchen opens to a private patio overlooking the scenic property. The main level includes a lovely office

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    35 Gobblers Knob Rd, Pawling, NY 12564
  • /6

    $79,000

    $9K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $171,739 per Acre

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

    Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531
  • /11

    $229,000

    • Land
    • 6.63 Acres
    • $34,540 per Acre

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

    Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /50

    $699,000

    $51K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,687 Sq Ft

    6 Martingale Way, Pawling, NY 12564

    Welcome to 6 Martingale Way, an impressive 4-bedroom, 3.5-bathroom colonial offering nearly 4,700 square feet of living space in the highly sought-after Highlands community of Pawling, NY. From the moment you step inside, you'll be greeted by beautifully refinished hardwood floors that flow throughout the entire first floor, setting the tone for the quality and care found throughout this

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    6 Martingale Way, Pawling, NY 12564
  • /41

    $1,300,000

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

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    64 S Quaker Hill Rd, Pawling, NY 12564
  • /22

    $1,350,000

    $50K PRICE INCREASE
    • Land
    • 3.9 Acres
    • $346,154 per Acre

    178 Charles Colman Blvd, Pawling, NY 12564

    Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

    Agent Photo

    Vince Buccieri

    Today Realty Corp.

    178 Charles Colman Blvd, Pawling, NY 12564
  • /43

    $629,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    57 Buhleir Rd, Pawling, NY 12564

    Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side.

    Carolyn Ridenour Berkshire Hathaway HS NE Prop.

    57 Buhleir Rd, 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
  • /21

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    188 N Quaker Hill Rd, Pawling, NY 12564

    Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

    Gillian Stewart Gillian Stewart Real Estate

    188 N Quaker Hill Rd, Pawling, NY 12564
  • /9

    $140,000

    $10K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $304,348 per Acre

    20 Hickory Ln, Pawling, NY 12564

    Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

    Tela Cook McGrath Realty Inc

    20 Hickory Ln, Pawling, NY 12564
  • /8

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,920 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
  • /8

    $619,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,652 Sq Ft

    0 Prospect St Unit KEY1024161, Pawling, NY 12564

    TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and

    Molly Roche eXp Realty

    0 Prospect St Unit KEY1024161, Pawling, NY 12564
  • /39

    $460,000

    $35K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft

    17 Townsend Blvd, Pawling, NY 12564

    Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

    Martha Woodhouse Howard Hanna Rand Realty

    17 Townsend Blvd, Pawling, NY 12564
  • /31

    $995,000

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

    6 Byrds Hill Rd, Pawling, NY 12564

    Renovated Colonial near Quaker Hill, less than two hours from NYC and minutes from Metro-North. Board-and-batten exterior with black-trimmed windows set the tone: clean lines and deliberate detail. Inside, the kitchen anchors the main level - marble island with seating, patterned tile backsplash behind the range, double wall ovens, and a layout that opens naturally to dining and living spaces.

    Stephen Pener William Pitt Sothebys Int Rlty

    6 Byrds Hill Rd, Pawling, NY 12564
  • /7

    $125,000

    $10K PRICE DROP
    • Land
    • 31,798 Sq Ft
    • $171,233 per Acre

    0 Walnut St, Pawling, NY 12564

    .73 acre lot is located in the Village of Pawling! *Board of Health Approval is NOT required because the house can be hooked up to municipal water and sewer! Variance with fees is required to build. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants/pubs, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the

    Lisa Liffland McGrath Realty Inc

    0 Walnut St, Pawling, NY 12564
  • /50

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 1,968 Sq Ft

    40 Harmony Rd, Pawling, NY 12564

    Set on 5.6 acres in Pawling within the Pawling Central School District, this Colonial-style home offers a rare combination of acreage, character, and versatile living space. With 4 bedrooms, 2 baths, and 1,872 square feet, buyers searching for a home with land in Dutchess County, a property surrounded by mature trees, or a house with multiple indoor and outdoor gathering spaces will appreciate

    Virginia Corbett eXp Realty

    40 Harmony 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

    Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

    Richard Esman Douglas Elliman Real Estate

    41 and 43 Meeting House Rd, Pawling, NY 12564
  • /56

    $3,100,000

    • 3 Beds
    • 3 Baths
    • 3,600 Sq Ft

    809 N Quaker Hill Rd, Pawling, NY 12564

    Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property's idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling

    Raj Kumar Four Seasons Sotheby's Int.

    809 N Quaker Hill Rd, Pawling, NY 12564
  • /50

    $5,000,000

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

    618 Quaker Hill Rd, Pawling, NY 12564

    Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations.

    Jake Garay Serhant LLC

    618 Quaker Hill 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
  • /33

    $9,750,000

    $7M PRICE DROP
    • Land
    • 558.35 Acres
    • $17,462 per Acre

    225 Route 22, Pawling, NY 12564

    Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

    Shaylene Neumann Houlihan Lawrence Inc.

    225 Route 22, Pawling, NY 12564
  • /21

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    357 W Dover Rd, Pawling, NY 12564

    Spacious and affordable. This expansive ranch style home sits on an approximately 3 acres that feature beautiful mountain views from the back of the home. Due to the layout of the home the possibilities are nearly endless. It currently sits as a 3 bedroom and 3 bath home but with proper approvals additional bedrooms are possible. The are two garages on the property. The garage next to the house

    Daniel Balassone VYLLA Home

    357 W Dover Rd, Pawling, NY 12564
  • /36

    $699,000

    $16K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,629 Sq Ft

    921 W Dover Rd, Pawling, NY 12564

    A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

    Joyce Brennan-Zolnik BHHS Hudson Valley Properties

    921 W Dover Rd, Pawling, NY 12564

Why Live in Pawling

Pawling, NY, spans 45 square miles in Dutchess County, offering residents a blend of rural solitude and accessibility to New York City via an MTA station for an hour-long commute. The town features over 1,000 acres of protected parklands, including the Pawling Nature Reserve, where locals can hike the Appalachian Trail. Recreational options also include Dutcher Golf Course and Whaley Lake, the largest lake in the county, ideal for swimming, kayaking, and fishing. The Maybrook Trailway, part of the Empire State Trail system, provides scenic hiking opportunities. Pawling's housing market includes upscale single-family homes such as Colonial Revivals, ramblers, raised ranches, and split-levels, with exclusive areas like Quaker Hill offering large farms and multimillion-dollar properties. The central village features Craftsman and Victorian homes, while waterfront cottages are available in Holmes. Pawling Central School District serves the community with highly rated schools, including Pawling Elementary, Pawling Middle, and Pawling High. The private Trinity-Pawling School, an all-boys Episcopal boarding school, is also highly rated. Local amenities include grocery stores like Acme Markets and Hannaford along NY-22, and dining options such as O’Connor’s Public House downtown. Community traditions include the Pawling Farmers Market and the Pawling Concert Series, along with Decemberfest and Tree Lighting events. Commuters can reach Manhattan in an hour and a half by train or car, and New Haven, Connecticut, is accessible within two hours.

Frequently Asked Questions

What is the average home price in Pawling, NY?
Homes for sale in Pawling, NY have an average home price of $943,715.
How many homes have sold over the last 12 months in Pawling, NY?
63 homes have sold in Pawling, NY over the last 12 months.
What are the most popular zip codes in Pawling, NY?
The most popular zip codes in Pawling, NY include 12564, 12531, 12563, 12570 and 06784.
How much do you need to make to afford a house in Pawling?
The median home price in Pawling is $559,500. If you put a 20% down payment of $111,900 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $2,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $121K a year to afford the median home price in Pawling. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Pawling, NY?
Pawling, NY has highly rated public and private schools. Some of the best schools in Pawling based on Niche Grades are Trinity-Pawling School, Mizzentop Day School and Pawling High School. Browse all the schools in Pawling, NY to learn more.

Home Price Trends

Median Sale Price
$512,500
Median Single Family Sale Price
$599,500
Median Townhouse Sale Price
$385,000
Median 2 Bedroom Sale Price
$396,000
Average Price Per Sq Ft
$325
Number of Homes for Sale
20
Last 12 months Home Sales
63
Months of Supply
3.80
Median List Price
$559,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-6%
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