$489,619Average Value$272Average Price per Sq Ft21Homes 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
Tracy LaRosa,
an experienced agent in this area.
GreatSchools:
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On average, homes in Dudley, MA sell after 30 days on the market compared to the national average of 55 days. The median sale price for homes in Dudley, MA over the last 12 months is $450,000, up 2% from the median home sale price over the previous 12 months.
Significant price improvement! Modern luxury. Timeless design. Exceptional one-level living. Welcome to 73 Dudley Hill Road, where sophisticated design and effortless main-level living meet in this stunning 2025 custom built contemporary ranch. Enter inside to soaring vaulted ceilings, abundant natural light, rich hardwood flooring, and an open layout that feels both spacious and welcoming. At
Welcome home to this 3-Bedroom Attached Colonial Single Family with No Condo Fees & No Association Nestled in One of Oxford's Premier Neighborhoods, Area of Newer and Larger Homes in a lovely Country Setting just a few miles from Oxford Center Rte.395, and 20 minutes to Worcester and Ct. Walk into the fireplaced living room with a cozy eat in kitchen featuring ample cabinetry. A little TLC will
Karynsue Marchione-ReillyPark Place Realty Enterprises
Historic character meets modern living at 9 Cross Street! This beautifully renovated 4-bedroom home offers a rare combination of 1793 post-and-beam craftsmanship and the bright, open layout today’s buyers are looking for. Original exposed beams and beautifully preserved wide-pine floors add warmth and character throughout. At the heart of the home is a stunning eat-in kitchen featuring an
Rare opportunity to build your dream home in the charming town of Dudley! This fully approved 0.77-acre building lot is ready for construction with an approved septic design for a 3-bedroom home and an existing well already on site. Just bring your building plans and get started. Enjoy the perfect blend of small-town New England charm and convenience, with Dudley offering scenic surroundings,
Welcome to 12 River Court! Located close to downtown Webster but nestled on a dead-end street, you can enjoy 3 spacious bedrooms, a bright kitchen with stainless steel appliances, and a fenced in back yard to enjoy your privacy with river views. Some sweat equity is needed to make your vision shine, so bring your ideas and tool belt and watch the possibilities come back to life. Sale is subject
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.
A Contractor's Opportunity! This 8,000 SF (80' road front x 100' depth - rectangular shape) Residential Level Lot is for Sale at 3 Marshall Terrace, in Dudley MA. Great location in an established neighborhood circle of single & multifamily homes, tucked away off of Brandon Rd. Key resources are readily available for a construction project electric, municipal water & sewer and natural gas are at
Waterfront Opportunity – Pierpoint Meadow PondDiscover a rare offering of premium homesites overlooking the scenic Pierpoint Meadow Pond. This unique opportunity features a choice of three 1+ acre lots with stunning water views and one 5+ acre estate lot for added privacy and space. All lots include deeded water access. Each parcel will be fully prepared for your future home as perc tested and
Price adjustment on this oversized split ranch. Granite stairs outside leads you into this very open floor plan. Kitchen, Dining and Family room all sporting a cathedral ceiling. Great for a large family. 3 bedrooms upstairs including Main with half bath and a large partially finished basement for another bed or 2nd family room. Newer Buderus boiler, roof, windows, siding. Three season sun room,
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 1900. 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
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
Rare opportunity in Dudley! This beautifully maintained home offers modern finishes, comfortable one-level living, and exceptional versatility. Currently used as a single-family residence and permitted for two-family use, the property offers both flexibility and investment potential. The spacious main living area features vaulted ceilings and radiant heated floors, creating an open, inviting
NEW PRICE! Now offered at $625,000! Welcome to this beautifully maintained 2024 Colonial in desirable Pierpont Estates. This move-in-ready home offers over 2,000 sq. ft. of modern living space, a bright, open floor plan, and an easy, inviting flow throughout. Enjoy your morning coffee on the charming farmer's porch or unwind on the rear deck overlooking the peaceful backyard. **Why wait for new
Welcome home to this charming and well-maintained two-bedroom ranch nestled in the heart of Dudley, just moments from Shepherd Hill Regional High School and Dudley Middle School, with Nichols College nearby.This move-in-ready home offers comfortable single-level living with hardwood floors throughout, complemented by tile flooring in the kitchen and bathroom. The flexible floor plan currently
Property Id: 2830683 2 bedrooms and 1 bathroom apartment about 900 sq. ft in first floor off street parking available for rent September 1st, with new appliances and new kitchen cabinets and granite countertops and bathroom, laundry hook up on site, lead certified. Section 8 and Homebase accepted. Located in Dudley MA.
Property Id: 2605622 BUILD CREDIT! We will report your on-time rent payments to the credit bureau. Rent starting at $1,992 rooms include two bedrooms, living room, and kitchen. Awesome 2-bedroom 3rd Floor residence. Hardwood floors with plenty of natural light Your new home has a personal driveway with off-street parking for you. Private entrance to your home--no common
Property Id: 2443439 BUILD 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 light This two bedroom apartment is approximately 775 square feet,
Property Id: 2198016 BUILD CREDIT! We will report your on-time rent payments to the credit bureau. Rent starting at $1,792! * Awesome 2-bedroom on the first floor in a 6-family building This is approximately 775 sq ft. Has own private rear entrance that leads into the kitchen through a hallway. Kitchen is very spacious with lots of storage between the pantry closet and large
Recently renovated 2nd floor 1 bedroom apartment tucked away on a quiet dead end street with very little traffic and lots of natural light. Recent updates include new paint, flooring, cabinetry. Available November 1, 2026. This cozy 1 bedroom unit has it's own private entrance and off street parking. Close to all local hospitals. Conveniently located only 1.5 miles to route 395 route 12 and route
Welcome to 192 Lower Schofield Ave in Dudley! This spacious single-family rental offers 3 bedrooms, 2 full bathrooms, and approximately 1,568 sq. ft. of living space. The property features a two-bay garage, fenced-in backyard, and a dedicated laundry room with hookups (washer and dryer not provided). Rent includes water, sewer, electricity, trash removal, and snow removal. Tenant is responsible
Updated Two-Bedroom Apartment – Available NOW! This clean and inviting two-bedroom apartment is ready for move-in! The unit includes water, sewer, trash removal, snow removal, and landscaping in the rent. Enjoy comfortable, low maintenance living in a clean and updated space. First and last month's rent required.
Welcome to 11 1st Ave, Unit #2—a beautifully renovated, sun-filled 2-bedroom-plus, 1-bathroom apartment offering comfortable and functional living space in a convenient Dudley location. This inviting home features two generously sized bedrooms, with 2 more potential bedrooms on the upper floor each providing a private and comfortable retreat, along with additional flexible space to suit your
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