$479,436Average Value$262Average 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?
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GreatSchools:
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On average, homes in Dudley, MA sell after 33 days on the market compared to the national average of 57 days. The median sale price for homes in Dudley, MA over the last 12 months is $450,000, up 3% from the median home sale price over the previous 12 months.
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
Welcome home to this charming 3-bedroom, 1.5-bath Cape-style home located in Dudley, just a short distance to Nichols College. This well-maintained property offers a functional layout with comfortable living spaces and plenty of natural light throughout. The home features a spacious yard—perfect for outdoor entertaining, gardening, or simply enjoying the seasons. Inside, you’ll find additional
***OPEN HOUSE, Sunday, 5/3, from 12pm to 2pm*** This is one of the nicest homes you'll see on the market! With loads of updates, this charming 3 bed, 2.5 bath home is move-in ready with the perfect, large backyard! The stunning and spacious living room is truly a sight to see, with a captivating fireplace anchoring the main living area! The kitchen features updated stainless steel appliances and
Spacious and beautifully updated, this impressive 5-bedroom with 1st floor bedroom, 4 full bath home offers the perfect combination of comfort, style, and outdoor living. Room above garage could be a Bonus room,Teen Suite or Primary Suite! Featuring recessed lighting & hardwood flooring throughout every room on main level. The interior feels bright, modern, and welcoming. A New Roof adds peace of
BACK ON MARKET DUE TO FAILED BUYER RELOCATION PACKAGE. Be sure to put this on the top of your list. Lovely young 3 bedroom,3 FULL bath hip roof colonial. Beautiful open floorplan boasts exceptional updated spacious kitchen, w/ formal DR & oversized Cathedral ceiling FR. Plenty of space for holiday/family gatherings/ Full bath on 1st floor. Den/ office completes the appeal.Lovely gleaming hardwood
NEW CONSTRUCTION set on a private & scenic 2 acre lot, this elegantly designed home at 86 Ramshorn, offers 1980 sq ft of finished above-grade living space, privately set back from the road. A bright & spacious open layout awaits featuring vaulted ceilings spanning the living, dining area & kitchen. Stylish kitchen w/ granite counters, subway tile backsplash & an oversized island perfect for
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
Welcome to 11 Ardlock Pl., a private 4-acre retreat at the end of a quiet cul-de-sac in Dudley. Enjoy exceptional outdoor living with a full pickleball/tennis court, bocce court, patio with outdoor oven, fruit trees, vegetable gardens, and a circular driveway with parking for 40+ cars. Inside, this 3,500+ sq ft home offers 4 bedrooms, 3 baths, a kitchen with Vermont soapstone counters and
Land for sale located at the end of Mason Road and Dudley Oxford Road. Part of the land is located behind properties, if interested to add to your land, that is a possibility. Lot size- 0.45 acres. Buyer/agent to verify all information and do their own due diligence to determine if land is buildable.
Nestled in the heart of Dudley, Massachusetts, this residence at 25 Quinebaug Rd presents an opportunity to own a piece of New England charm with a history dating back to 1901. Situated on a 6534 square foot lot, offers a blend of classic architecture and the potential for modern living. With a generous 2229 square feet of living area spread across two stories provides ample space for comfortable
Welcome home to this charming 3-bedroom, 1.5-bath Cape-style home located in Dudley, just a short distance to Nichols College. This well-maintained property offers a functional layout with comfortable living spaces and plenty of natural light throughout. The home features a spacious yard—perfect for outdoor entertaining, gardening, or simply enjoying the seasons. Inside, you’ll find additional
Welcome to 6 Lerner Dr in Dudley — Priced below market value! This raised-ranch sits on a quiet dead-end road. Featuring 3-beds & 2-baths this home offers a spacious living room with hardwood floors and a cozy fireplace, plus a large eat-in kitchen with a breakfast bar. The primary bedroom includes its own full bath. Generous sized bedrooms. Small 3 season porch overlooking a large backyard that
This EAST FACING Custom, Hip roof Colonial with FRESH INTERIOR PAINT (2025), offers spacious rooms and elegant details like chair rails, crown molding, and wainscoting. RENOVATED Eat-in Kitchen (2022) with island, BRAND NEW HARDWOOD FLOORS, and peninsula which opens to a cozy family room with a wood stove insert and a heated sunroom—ideal for entertaining. In addition there are Hardwood floors in
Michael MathieuMathieu Newton Sotheby's International Realty
Well-maintained 1900 home blending classic charm with thoughtful updates! The kitchen features a granite center island, Formica countertops, and a stove, refrigerator, washer, and dryer. (7 years) The bathroom includes a granite vanity and tub/shower combo. The FR/Dining Room is spacious and well-lit. Major improvements offer peace of mind: boiler and oil tank (4 years), roof (8 years), and newer
Set on almoat 8 secluded acres in North Dudley near the Oxford line, this stunning gated estate combines privacy, elegance, and modern amenities. The main residence offers 5 bedrooms, 3 full and 1 half baths, with an open-concept living, dining, and chef-ready kitchen. The finished lower level features a full kitchen, living and dining space, 2 bedrooms, and 1.5 baths—perfect for in-law or guest
This property is available. Please inquire on this site to schedule a showing. Welcome to your new home at 11 1st Avenue, Dudley, MA 01571. This charming first-floor apartment offers a spacious and inviting living environment with modern upgrades. Step into a bright and airy living room with large windows that let in plenty of natural light, complementing the sleek, new flooring. The
Bright and spacious second-floor remodeled apartment ready for immediate move-in, offering plenty of natural light and a comfortable, open layout. The unit features oil heat and includes access to a shared backyard, perfect for relaxing or enjoying outdoor space. This well-maintained apartment has been recently updated, providing a clean and modern living environment. Please note there are no
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
Beautifully updated unit in the desirable Stonegate Condominium Complex. Features brand-new carpeting, fresh paint, new light fixtures, and updated thermostats throughout. Kitchen includes a new refrigerator and oven. Fully renovated bathroom with new vanity, toilet, and modern finishes.Enjoy low-maintenance living with rent including trash removal, landscaping, snow removal, and exterior
NEW CARPETS THROUGHOUT ALL GREY NOW! Spacious and well maintained 3 bedroom, 1 bathroom apartment offering approximately 1,680 sq ft of living space directly across from the Dudley Library. This bright unit features large rooms, classic woodwork, and plenty of natural light throughout. Convenient location close to local shops, restaurants, parks, schools, and major routes for commuting. Gas and
Beautifully updated unit in the desirable Stonegate Condominium Complex. Features brand-new carpeting, fresh paint, new light fixtures, and updated thermostats throughout. Kitchen includes a new refrigerator and oven. Fully renovated bathroom with new vanity, toilet, and modern finishes.Enjoy low-maintenance living with rent including trash removal, landscaping, snow removal, and exterior
Beautifully updated 2-bedroom, 1-bath apartment offering a seamless blend of comfort and style. The bright, open living area features abundant natural light and modern flooring, creating a welcoming atmosphere for everyday living and entertaining. The renovated kitchen showcases sleek cabinetry, updated stainless appliances, stone countertops, and a stylish tile backsplash. Spacious bedrooms
Property Id: 2443439BUILD CREDIT! We will report your on-time rent payments to the credit bureau. Rent starting at $1,792! Rooms include two bedrooms, living room, and kitchen.* All animals considered! ** Awesome 2-bedroom on the 2nd floor in a 6-family building* Hardwood floors with plenty of natural lightThis two bedroom apartment is over 700 square
Looking for a serene place to get away from the stresses of the day? Look no further than this lovely waterfront home to rent! This charming 1 / 2 bedroom home will ease your stress within moments of entering this oasis! Looking for credit score 650 or better, clean background, no evictions. First, last and security
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