$572,861Average Value$2,597Average Price per Sq Ft2Homes For Sale
Pawling locals have rural space and still commute to New York City
The town of Pawling stretches 45 square miles across the trees and rolling pastoral spread of Dutchess County and is anchored by the small commercial village of the same name at its heart. Pawling residents appreciate the rural solitude that comes with the homes here. They also have access to over 1,000 acres of protected parklands and are connected to an MTA station for an hour-long commute to New York City. “[There was a] boom of work-from-home residents due to Covid,” says Shannon Tully, a longtime Pawling local and associate broker with McGrath Realty. “A lot of people still work hybrid, there’s also a lot of commuters and second homes in Pawling.” It’s just as easy to find weekend residents and Big Apple commuters as it is to find local Dutchess County workers living in Pawling, making it a community where many lifestyles intersect.
Some homes in Pawling are separated by massive plots of land.
The village of Pawling is small and friendly with a classic feel.
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Upscale single-family homes and a prominent land market
The median single-family home price in Pawling is $637,500, which is 32.8% higher than the median home price for Dutchess County. Styles vary by location and include Colonial Revivals, ramblers, raised ranches and split-levels around town. “We have Quaker Hill, a very exclusive high-end area with large farms, lots of land and multimillion-dollar real estate opportunities,” says Tully. The larger town is split into small communities with distinct atmospheres, like Quaker Hill to the east, with secluded lots and several horse farms. In the Holmes area, waterfront cottages are available beside Whaley Lake and the Empire State Trail. Folks seeking a small-town rural feel close to local businesses and public transit can find a handful of Craftsman and Victorian homes in the central village of Pawling. There is also a significant land market around town, with multi-acre parcels ranging from $150,000 to $500,000.
Stunning lawns and well kept homes are common in Pawling.
Pawling features many homes that sit on large lots amongst local farms.
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Pawling Nature Reserve and Whaley Lake are big recreational hubs
Pawling Nature Reserve is a protected green space north of town. Locals can enjoy dense forests and native wildlife while hiking the famous Appalachian Trail, which stretches over 2,000 miles from Maine to Florida. South of Pawling is Dutcher Golf Course, the oldest 9-hole municipal course in the country, having been open for residents and guests since 1890. Residents can also swim, kayak, or fish for yellow perch at Whaley Lake, the largest lake in Dutchess County, on the western end of town. Beside the lake is the Maybrook Trailway, connected to the larger Empire State Trail system. Along Maybrook Trailway, hikers can see abandoned railcars that were converted into vacation rentals for New York City Sanitation workers back in the 1950s.
Along Whaley Lake you can enjoy waterside living in Pawling.
The Pawling Nature Preserve features hiking trails and swimming in a secluded and scenic setting.
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Groceries along NY-22, and diners are downtown
Locals can head to Acme Markets or Hannaford along New York state Route 22 to grab groceries. O’Connor’s Public House sits in Pawling’s quaint downtown corridor. This family-owned and operated Irish pub offers a full menu of pastas, steaks and fish and chips, to pair with its selection of brews.
Cosimo's Trattoria near Pawling is a go-to for LaGrange locals craving handmade pasta and cocktails.
Hannaford in Pawling is where shoppers stock up on groceries.
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Farmers markets and local concerts are longtime traditions
The Pawling Farmers Market is a 17-year town tradition, where locals can pick up locally sourced produce, fresh eggs, meat, honey and other goods on Saturday mornings from June through September. The Pawling Concert Series has been going on for over 50 seasons and takes place at several venues across the Pawling-Trinity School campus. During the holidays, there’s Pawling’s Decemberfest and Tree Lighting, where neighbors come together to celebrate the community, and kids can meet Santa and receive gifts.
Pawling Farmers Market is great for getting fresh produce and local goods.
Pawling's St. Patrick's Day is a celebration that is highly anticipated and leaves shamrocks on the ground all year long.
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Subway access to Manhattan from home
“It’s one of the last walking Metro North villages around the area outside of Westchester and Putnam counties,” says Tully. “[It’s a] direct line to New York City, still an hour and a half drive, you’re just getting on 22 and driving straight there.” Commuters in town can hop on an MTA train from the Pawling Train Station to reach Manhattan in an hour and a half. Drivers can reach the Big Apple in the same time, after a 65-mile drive along either Taconic State Parkway or Interstate 684. Due to Pawling’s proximity to the Connecticut border, locals can also reach New Haven, Connecticut in under two hours on Interstate 84.
The Pawling train station links commuters to New York City in about an hour.
Route 22 runs through Pawling and allows for an easy commute.
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Pawling public schools and Trinity-Pawling School
Pawling Central School District serves the greater community for education. Students can attend Pawling Elementary and Pawling Middle, which both earn B-plus ratings from Niche, while Pawling High gets an A-minus. For private options, the town also hosts the A-plus-rated Trinity-Pawling School, teaching grades seven through 12. This all-boys Episcopal boarding school is ranked by Niche as the best private school in Dutchess County.
Pawling High School located at 30 Wagner Drive in Pawling prepares students for college.
The Trinity-Pawling School offers a private education for Pawling students.
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Written By
Maxwell Olarinde
Photography Contributed By
Stephen Mihalchik
Interested in learning more about homes in this area?
Reach out to
Veronica Newton,
an experienced agent in this area.
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On average, homes in Pawling, NY sell after 13 days on the market compared to the national average of 70 days. The median sale price for homes in Pawling, NY over the last 12 months is $225,000, down 34% from the median home sale price over the previous 12 months.
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
Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your
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. This charming, expansive ranch home is thoughtfully designed to suit a variety of living
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
Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your
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. This charming, expansive ranch home is thoughtfully designed to suit a variety of living
Welcome to 39 Nathan Pierce Court – a beautifully updated 3-Bedroom, 2.5 Bath townhouse located in the desirable Deerfield Ponds Community. Offering 1,600 sq ft of thoughtfully designed living space, this home combines modern upgrades with everyday comfort and convenience! The kitchen features stainless steel appliances, generous cabinet space, and a bright eat-in area perfect for casual meals or
Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit
Now Leasing: the Pawling Commons—a brand-new rental complex offering an unparalleled living experience in the heart of the Village of Pawling. This modern three-story building features 15 luxury rental apartments, thoughtfully designed for both comfort and convenience. With a mix of one studio, two one-bedroom, and twelve two-bedroom apartments, residents can choose the perfect space to suit
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