$589,695Average Value$337Average Price per Sq Ft21Homes 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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Pawling, NY sell after 70 days on the market compared to the national average of 58 days. The median sale price for homes in Pawling, NY over the last 12 months is $490,000, down 13% from the median home sale price over the previous 12 months.
Properties like this don't come along often! As you turn off the road, the world quiets. The driveway pulls you back through a canopy of mature trees, and by the time the house appears, you already feel the privacy with over five acres, buffered on all sides, thoughtfully expanded and upgraded far beyond its 1975 origins. Step inside to a living room anchored by a stone fireplace, original
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
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
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
Nestled in the heart of historic Quaker Hill, this bucolic property offers timeless charm just a stone’s throw from the iconic Meeting House. Originally built in 1983, the home underwent a meticulous, top-to-bottom renovation in 2016, thoughtfully upgrading all major systems, finishes, and living spaces to modern standards while preserving its serene setting. The residence is exceptionally
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
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
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
Nestled on 3.37 picturesque, partially wooded acres, this beautifully maintained 3-bedroom, 3.5-bath residence offers an exceptional blend of privacy, comfort, and natural beauty. Surrounded by mature trees and tranquil landscapes, the property provides a peaceful retreat with expansive open areas perfect for outdoor recreation, entertaining, gardening, or simply enjoying the serene setting.
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.
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.
Commuter’s Dream in the Heart of the Village! Brimming with historic character and modern convenience, this charming second-floor apartment is located right in the vibrant center of Pawling, NY, just 0.2 miles from the Metro-North train station for a seamless commute to NYC in well under two hours. The spacious layout features stunning original wood crown molding, an oversized living room, a
Rare Village of Pawling 2 bedroom, second floor apartment. Open concept Living Room allows you to use the space to fit your needs. Remodeled kitchen with luxury vinyl flooring, stainless steel appliances, granite counter tops and white shaker cabinets for lots of storage. Beautiful, weathered wood backsplash adds a designer touch. Updated bathroom with tub/shower enclosure, white vanity and
At your fingertips! Everything the Village of Pawling has to offer - Metro North, Lakeside Park, shopping, restaurants and services. Clean, affordable, two bedroom second floor apartment with newer windows and lots of extra storage. Good sized Living Room with plenty of sunshine. Eat in Kitchen with maple cabinets, recessed lighting and tile floor makes this fully functional for your cooking
$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
Two room studio in the historical Village of Pawling. Ground floor, private entrance. Convenient parking. Walk to Metro-North, shopping, laundry. No smoking/pets Call only
A beautifully renovated antique colonial near Quaker Hill, available for the full summer. The layout offers plenty of room to spread out with an open kitchen and oversized center island, dining and living area with a fireplace, and a separate den for quiet downtime. The main-floor primary suite includes a private bath with both a shower and soaking tub. Three additional bedrooms and a full bath
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
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
