$583,841Average Value$318Average Price per Sq Ft13Homes 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
Valerie Port,
an experienced agent in this area.
GreatSchools:
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On average, homes in Pawling, NY sell after 67 days on the market compared to the national average of 55 days. The median sale price for homes in Pawling, NY over the last 12 months is $511,250, down 5% from the median home sale price over the previous 12 months.
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
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
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,
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
Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers
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
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
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
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
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
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
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
Bright & Spacious 3-Bedroom Apartment in Private Setting – Close to Train, Shopping & Schools Enjoy privacy and convenience in this light-filled 3-bedroom, 2.5-bath apartment located in a well-maintained three-family home on a quiet, secluded road just off the main thoroughfare. This spacious apartment offers the perfect balance of peaceful living while being minutes from shopping centers,
Charming and spacious 2-bedroom, 1-bath apartment featuring high ceilings, skylights, and ceramic tile floors throughout, creating a bright and open living environment. This inviting home offers a private entry, providing added privacy and convenience. The apartment is filled with natural light thanks to the skylights and generous ceiling height, giving the living spaces an airy and comfortable
$30k/month summer. Inquire for other terms. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond. Long driveway with mature landscape, this hideaway provides pure
Charming completely rebuilt carriage house with 1 BR apartment upstairs. General foyer, stairs to landing & apartment. Spacious EIK, large living room, large bedroom, full bathroom w/tub & shower. Stack able washer & dryer. The kitchen has butcher block counters, stainless appliances including fridge, stove, dishwasher & microwave. Deep sunny windows, central air & heat pump, 900 square feet of
Fully renovated spacious apartment in the Heart of Pawling Village. Everything you see is brand new. Lives like much more than a simple 1-bedroom apartment. Just Minutes to downtown and historic Main Street, this bright and charming unit holds the perfect balance of character and convenience. Situated on the first floor of a classic 1920s Cape Cod-style home, featuring a spacious layout with
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