$480,951Average Value$267Average Price per Sq Ft15Homes For Sale
Dudley is a historic town on the Massachusetts-Connecticut state line
Dudley, Massachusetts, was once the midway point for travelers from Boston to Hartford. During the Colonial era, folks parked their carriages at the Black Tavern, a historic inn that still stands today, and spent the night here on the Massachusetts-Connecticut state line. Into the 19th century, Dudley was known for its rolling farmland and textile mill along the Quinebaug River. While those industries have faded with time, the community about 20 miles southwest of Worcester maintains its rural feel with family-owned farmstands, acres of conservation land and houses on large, green lots. “This area is almost entirely rural,” says Mary-Jo Demick, a real estate agent with Aucoin Ryan Realty who has sold several homes in the area. “People who move here are looking for quiet. They want to be removed from the hustle and bustle.”
Dudley historic district dates back to a pre revolutionary settlement.
Visit the Black Tavern historic landmark in Dudley.
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Town history in Dudley Historic District
The Dudley Hill Historic District runs along Center Road. The district’s southern end is marked by Nichols College’s campus, and the northern end by the Village Cemetery. Listed on the National Register of Historic Places, the 200-acre hilltop hamlet is the site of Dudley Hills’s original Colonial-era settlement. Some notable buildings include the William Carter House, the oldest standing building in Dudley, where the town’s first meeting was held; Conant Memorial Church, a stately brick building built in 1890; Black Tavern, a Colonial-period inn that houses a historical society; and Dudley Grange, a fraternal organization that advocates for agriculture and rural America. Every September, Dudley Grange hosts the Apple Festival, where people can bob for apples, listen to live music or munch on caramel-covered honeycrisps.
The William Carter house is the oldest standing building in Dudley.
The historic Nichols College calls the historic district of Dudley home.
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Ample outdoor recreation, from hiking to golfing
Outdoor enthusiasts enjoy acres of protected land in Dudley. The Tufts Branch Wildlife Sanctuary lies along Healy Road and the park’s 1-mile trail loops over boardwalk bridges and through catnip wildflower meadows. Wieloch Woods Sanctuary is known for its eastern pine tree groves and birdwatching decks, where folks might catch a glimpse of a red-bellied woodpecker. Hikers and bikers can access the Quinebaug River Valley Rail Trail. The trek has gravel, grass and paved routes, passing mature sweet birch trees and hydropower dams. The trail is still being expanded, and it will eventually stretch 11 miles. The river’s rocky shoreline has spots for anglers to catch rainbow trout, while boaters can launch a kayak from one of several ramps. For a summer day in the sun, residents can go to the sandy shoreline of Merino Pond at Dudley Beach off Lakeview Avenue. The body of fresh water is permitted for swimming, non-motorized boating and fishing. Located on the Nichols College campus, Dudley Hill Golf Club is another popular outdoor space. The 9-hole course, open to the public, features winding bluegrass fairways opened in 1926.
Dudley beach is a popular spot to enjoy the water.
Dudley residents enjoy walks through Wheelock Woods.
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Homes on large, secluded lots
Most properties in Dudley sit along narrow two-lane roads, where mature oaks and red maple trees dot grassy front lawns. Single-family homes are spread out from each other, with expanses of green space between them. “A lot of these houses will sell in less than a week because of the acreage,” Demick says. “Even if it's just an empty lot, every type of property sells fast.” Common styles include Colonial Revivals, Cape Cods, New Traditional and ranch-style homes. Center Road is lined with the town's oldest and most well-preserved late 19th-century houses, and restored gambrel farmhouses and Colonial Revivals sit on 2-acre lots. Some properties in Dudley back up to Merino Pond, giving residents private access to the water. Dudley’s median single-family home price is about $445,000; however, costs can depend on a property’s size, age and condition. Some townhouses and condos are also available, with prices from $180,000 to $380,000.
Colonial revival homes are popular throughout Dudley.
Cape homes are a beloved style throughout Dudley.
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Dudley-Charlton Regional School District and Nichols College
Students are zoned for the Dudley-Charlton Regional School District. They can attend Mason Road School for prekindergarten through first grade and Dudley Elementary for second through fourth grades. Mason Road School gets a B-plus grade from Niche, while Dudley Elementary scores a B. Next, they can attend Dudley Middle, which gets a B-minus and offers extracurriculars like Lego robotics. They can finish their public education at Shepherd Hill Regional High School, which earns a B from Niche. Shepherd Hill’s Career Pathways program offers certifications in global awareness, engineering, biomedicine and communication. The high school’s annual Fall Festival includes trunk-or-treat, pumpkin decoration, a petting zoo and more.
Nichols College, a private, four-year school with various programs for undergraduates and graduates, is in Dudley. The school is small, with just over 1,000 students, but the athletics program is robust, having won 28 conference championships since 2007.
Mason Road Elementry School in Dudley serves students in grades PK-1.
Dudley Elementary School students enjoy a student teacher ratio of 13:1.
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Local options along West Main Street, big-box shopping in nearby towns
West Main Street is the area’s main commercial corridor, lined with local businesses, from body shops to hair salons. Residents can head to Dunkin’ in the morning or opt for a local choice, like Sturbridge Coffee Roasters. Dudley House of Pizza is a popular lunch or dinner spot, serving thick-crust pies and hearty calzones, while Yummy’s is the community’s go-to for Chinese cuisine. Further up West Main sits the Dudley Plaza Shopping Center, which has a Park ‘N Shop grocery store, along with a Dollar Tree and a few other businesses. Farther out of town, Walnut Lane Farm spans 230 acres and sells grass-fed beef, raw milk and free-range eggs year-round.
“There isn’t a super busy downtown area here, so people have to drive outside of town for more shopping and eating options,” says Christi Smith, a Realtor with Hometown Realty who has sold several homes in the area. For a traditional New England downtown experience, with rows of Colonial- and Federal-style shops and restaurants tucked between historic churches, downtown Southbridge is about 7 miles west of the center of Dudley, and downtown Webster is about 3 miles east. Nationally known restaurants and retailers like Applebee’s and Walmart Supercenter are 13 miles away at The Center at Hobbs Brook. For hospital visits, UMass Memorial Health’s Harrington location is about 8 miles west.
Stop into the Dudley favorite, Yummy, for fantastic Chinese dishes.
Park 'n Shop provides Dudley residents with a wide selection of groceries.
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Getting around Dudley
The Webster-Dudley-Southbridge Shuttle runs along Main Street and travels through its namesake towns. Dudley is less than 10 miles from interstates 90, 84 and 395. Drivers can access other city centers, like Springfield or Worcester, in under an hour. “This is a commuter-heavy area,” Smith says. A 60-mile drive east leads to downtown Boston, and a 50-mile trip southwest ends in Hartford. For air travel, Worcester Regional Airport, a small domestic airport with limited flights, is about 20 miles north, while Boston Logan International Airport is about 60 miles east.
Written By
Adreanna DeMarino
Photography Contributed By
Colin Gee
Video By
Jarrod Bock
Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this area.
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On average, homes in Dudley, MA sell after 27 days on the market compared to the national average of 52 days. The median sale price for homes in Dudley, MA over the last 12 months is $440,000, up 5% from the median home sale price over the previous 12 months.
Welcome to Sawmill Rd in Dudley MA -- a perfect blend of comfort and convenience in a highly sought-after neighborhood. Nestled just a short stroll from Merino Pond and Dudley Beach, this charming ranch offers one-level living at its finest. The beautifully remodeled eat-in kitchen features modern appliances, and finishes, ideal for gatherings and entertaining. The home also boasts a renovated
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This home combines the privacy of a 2 acre wooded lot and the quality of a home with elegance, quality, design, and energy efficient mechanical systems. Hardwood 3/4" oak tongue and groove flooring are throughout the main level and second floor including the staircase. The GREAT ROOM with a gas fireplace and cathedral ceilings is spacious and can accommodate any size furnishings. An 8' center
EXQUISITE EXECUTIVE HOME ON 4.5 ACRES IN COMMUTER FRIENDLY DUDLEY MA. Incredible amount of upgrades in the past two years make for a stunning, move-in ready retreat. The home has been painstakingly remodeled w/ high-end finishes inside & out. ALL NEW KITCHEN by Kitchen Assoc. SS GE Monogram, Cafe and Wolf appliances. NEW ISLAND & PANTRY ADDED. Existing HW's refinished, NEW CHERRY HW's added to 3
Three family with one unit currently vacant. Owner in process of renting for 1000/month. Parking in front was added. Hot Water tank replace on 1st & 3rd floor.
Charming Cape style home on large, level fenced-in lot near Merino Pond and Dudley Beach! Welcoming interior decor with hardwood flooring, recent paint, new hot water heater replaced in January 2024 & furnace installed in 2025! Roof approximately 2016, vinyl fencing approximately 2015. Backyard is completely fenced in making it the perfect oasis for young children & pets Garage attached through
This 2-bedroom, 1-bathroom property offers 900 square feet of living space. The living room provides ample room for relaxation and includes air conditioning for comfort. The kitchen is equipped with a dishwasher and features convenient access to the washer and dryer. Each bedroom is designed for functionality, providing sufficient space for furnishings. The bathroom includes beautiful fixtures
One bedroom apartment available NOW. Rent includes HEAT, water, sewer, trash, snow removal, and landscaping. Off-street parking available. Convenient washer/dryer in building. First and last month's rent required.
Welcome to the Lake! Located in peaceful Dudley MA, right off major highways (Pike / 395) you will find this retreat easily accessible and remote at the same time. My wife and I were fortunate to spend summers at the lake with our family so we decided to buy and fix this cottage up to give our family that same beautiful experience. While called a pond, Pierpont Meadow is over a mile long and wide
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