$730,230Average Value$333Average Price per Sq Ft8Homes For Sale
Community of families and commuters southeast of Worcester
What draws homebuyers to Upton? Suburban living with a tucked-away feel and convenient access to Boston’s outer beltway: That would be a good place to start. This Worcester County town is seeing a rise in demand, and buyers are willing to pay more to make its spacious lots their own. “It’s really pretty,” says Carla Horn, a real estate agent with ERA Key Realty Services who lives in neighboring Whitinsville. “There are the folks that have grown up there or lived there for quite a while, but there’s also the influx of the young commuter crowd or the ones just starting families,” Horn continues. Housing runs the gamut from modest ranch-style homes to preserved Victorians and classic colonials at higher price points.
Upton State Forest surrounds the residents homes.
Upton Town Beach welcomes you in to relax with a spectacular view of Pratt Pond.
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Colonial and ranch-style homes with spacious yards
Upton’s rustic feel is owed to its layout: a network of subdivisions is connected by winding two-lane roads. Shaded by mature trees, well-manicured spacious lots are the norm, with many stretching at least an acre, providing homeowners plenty of lawn space. Some homes stand well off the area’s curving country roads, creating additional privacy. Houses here span the eras, with some dating back to the 18th and 19th centuries. Most homes were built throughout the 20th century, though construction continues today. Buyers will primarily find colonial, Cape Cod and ranch-style homes, with some Victorian dwellings near the town center. Those on the hunt should note that there’s fervent demand for this community right now. The average sale price in Upton has increased 18% over the last year, with homes listing anywhere between $325,000 and $1 million.
Upton residents get ready for fall by decorating their front porch.
Some Upton homes welcome their owners with large front lawns and driveways.
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Schools in the Mendon-Upton Regional School District
Children here can start at Memorial Elementary, earning a B-plus from Niche, where they can enroll in the district’s Spanish Immersion Program to begin on a path toward dual-language proficiency. By the time students reach fifth grade at B-minus-rated Miscoe Hill Middle, they can take half of their classes in Spanish and the other half in English. Students can move on to Nipmuc Regional High, with an A-minus, where they can graduate with a Massachusetts Seal of Biliteracy, recognizing proficiency in English and a foreign language. Teens can also apply to Blackstone Valley Regional Vocational Technical High School, a big draw for the area. “It’s for kids who want to go into trades. They have all sorts of profession-geared classes for kids who may not want to go to college. It’s very competitive to get into,” Horn says. As for private education, Horn says Whitinsville Christian School is a popular option.
Memorial Elementary School, located in Upton, is a great school for children K-5.
Westborough High School welcomes its students every morning with its beautiful entrance.
A highly rated school, Nipmuc Regional High School Is nestled in the town of Upton.
Blackstone Valley Regional Vocational Technical High School .
Miscoe Hill Middle School is located right outside of the town of Upton.
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Multiple ponds for water recreation
Anglers here love Pratt Pond, a year-round destination for catching bass and crappie. In the warmer months, residents can hang out on Kiwanis Beach and play soccer and basketball. More nature can be enjoyed at Dean Pond within the Upton State Forest. The forest totals 2,660 acres and includes miles of trails. Visitors can hike or bike to the pond for fishing, and in the winter, adventure seekers can go cross-country skiing or snowmobiling. Over at Upton Community Center, families can romp around the playground before settling in for story time at the Upton Library. The community center offers group fitness classes like yoga.
At heart of Upton you can find Pratt Pond, where residents go to enjoy a beautiful day.
Mill Pond connects the town center of Upton and Pratt Pond.
Upton Veterans Memorial Playground is a top favorite for kids and parents.
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Dine and shop in Upton’s town center
Local restaurants and businesses are clustered along Main and Milford streets in the town center. Rose Garden Restaurant & Pub is a popular spot for pizza and burgers, while The Little Coffee Bean is where residents go for coffee and bagels. After tasting the small-batch brews at Rushford & Sons Brewhouse, residents can walk to Nevermind Shop to browse its extensive collection of vinyl, cassettes and vintage band T-shirts. Residents can drive about 5 miles to the Shaw’s in Milford for groceries. The town is also where Upton residents can shop at brands like Target and Lowe's.
Main & Milford street are popular areas for all your shopping needs.
Locals can chose from many beers on tap at Rashford and Sons Brewhouse.
Stop by on your next lunch break at The Little Coffee Bean in Upton, Massachusetts.
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Quick drive to Interstates 495 and 90
Sidewalks line some of the subdivisions here, but without public transportation, Upton residents drive to get around, utilizing the area’s proximity to Interstate 495, which links to Interstate 90 for commutes to Boston, about 40 miles away. Worcester, the second most populous city in the state, is a 14-mile drive via State Route 140.
Houses of Worship
With ties to the town’s beginnings, The United Parish of Upton, an inclusive Christian congregation, is significant to live here, hosting community events and running a year-round food pantry. Residents seeking a faith community have other options within driving distance, including Immanuel Chapel Orthodox Presbyterian Church, New England Buddhist Vihara & Meditation Center, Masjid Al-Ikhlaas (The Islamic Society of Greater Milford) and synagogue Temple Beth Torah.
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Interested in learning more about homes in this area?
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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.
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On average, homes in Upton, MA sell after 35 days on the market compared to the national average of 54 days. The median sale price for homes in Upton, MA over the last 12 months is $780,000, up 20% from the median home sale price over the previous 12 months.
Move right into this beautifully updated Fieldstone townhouse offering low-maintenance living in a peaceful, village-like setting. The open main level features new hardwood floors in the dining and living rooms and a stylish kitchen with brand-new stainless appliances—perfect for everyday living or entertaining. Upstairs offers two spacious bedrooms and a full bath, with a convenient half bath on
Discover townhome living in 5 Boot Shop Road U:31, Upton, MA. Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Ask about our 20k developer incentive. Designed for active adults, Cobblers Creek is a
Welcome to Cobblers Creek, a serene 55+ community in Upton offering detached condominiums designed for active adults seeking low-maintenance living with commuter convenience. Tucked within a peaceful tree-lined setting yet close to Route 495 and the Mass Pike, this community blends privacy with accessibility. The Cardinal townhome floor plan features open-concept living with an eat-at island
Here's your opportunity to build your dream home in the quaint and serene town of Upton. Over 3 acre wooded lot located on a scenic country road yet close to downtown. Potential to build a home with views of Boston! Zoned for a single family. Perc test done for septic. Per town, public water connection is possible. Excellent access to I-495 and the Mass Pike for commuters. Can be purchased on its
Melissa EllisonMathieu Newton Sotheby's International Realty
Where Luxury Meets Country! Welcome to this beautifully updated 4BR, 3,000+ sq ft home in scenic Upton. Perfect for entertaining with spacious foyer, formal dining & sitting room, plus expansive family room off the remodeled gourmet kitchen with quartz countertops, stainless steel appliances, double oven, compactor & decorative cabinet lighting. Upstairs offers 4 bedrooms & 2 full baths incl. a
Brittany PalmerinoMathieu Newton Sotheby's International Realty
Finishing touches were completed after the photos. This beautifully updated 2,887 sq. ft. single-family home offers stunning views of Pratt Pond and easy access to I-495. Renovated in 2024–2025, it features all-new siding and windows, a brand-new asphalt driveway and parking area, and a commercial-grade fire safety system. Inside, enjoy spacious, flexible living areas perfect for remote work or
Move right into this beautifully updated Fieldstone townhouse offering low-maintenance living in a peaceful, village-like setting. The open main level features new hardwood floors in the dining and living rooms and a stylish kitchen with brand-new stainless appliances—perfect for everyday living or entertaining. Upstairs offers two spacious bedrooms and a full bath, with a convenient half bath on
135 Main St contains 34 units comprised of (22) 1-Bed/1-Bath units and (12) 2-Bed/1-Bath units. The Property, previously known as The Upton Inn, has undergone significant renovations since its acquisition in August of 2024. This has included renovations of most units including new kitchens and bathrooms with condo quality finishes, updated flooring and painting of the units’ interiors. 135 Main
A timeless New England farmhouse-style under construction on Lot 2, sitting on 4.3 scenic acres & offering 3,586 square feet of living space. Facing east, the home is perfectly positioned to capture fantastic sunrises—best enjoyed from the inviting farmer’s porch, which adds curb appeal & serves as the perfect place to start your day w/ a morning coffee or unwind in the evening. Designed for
Team MetrowestBerkshire Hathaway HomeServices Commonwealth Real Estate
Discover townhome living in 5 Boot Shop Road U:31, Upton, MA. Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Ask about our 20k developer incentive. Designed for active adults, Cobblers Creek is a
Discover townhome living in 15 Shoemaker Lane U:7, Upton, MA. Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans,
PREPARE TO FALL IN LOVE! Relocating Executive Seller is sad to leave this meticulously maintained DREAM home, loaded with UPDATES throughout, including a BRAND NEW HEATING SYSTEM! Plus a private, FENCED & FLAT backyard! Step inside to an inviting OPEN CONCEPT floorplan, with beautiful BRAND NEW FLOORING & an abundance of natural light throughout. A large kitchen offers plenty of space for the
Welcome to Cobblers Creek, a serene 55+ community in Upton offering detached condominiums designed for active adults seeking low-maintenance living with commuter convenience. Tucked within a peaceful tree-lined setting yet close to Route 495 and the Mass Pike, this community blends privacy with accessibility. The Cardinal townhome floor plan features open-concept living with an eat-at island
5.45± acres zoned General Business (GB) located along West Main Street (Route 140) in Upton. This versatile parcel offers strong road frontage, visibility, and flexibility for a variety of commercial, professional, mixed-use, or investment opportunities, subject to Town approvals. The GB zoning district supports a broad range of business and service uses, making this an ideal site for
Exceptional investment opportunity in Uxbridge! This fully rented three-family property offers immediate, reliable cash flow with all units currently leased at market rents. The property consists of two spacious three-bedroom units in the main building and a separate, single-family detached one-bedroom unit—an ideal configuration for strong tenant demand and income diversification. Each unit
Lake lovers and boaters, welcome home! Beautifully renovated single family Lake Maspenock home in Upton with handicap access & peaceful water views. This spacious home has an extra-large main bedroom with an en-suite bath. The home was recently renovated; move-in ready. There's a handicap ramp for accessible entry to 1-floor living & access to a private boat ramp! Updates include new quartz
Kessel Shea TeamBerkshire Hathaway HomeServices Commonwealth Real Estate
This charming colonial home located in Upton offers 4 spacious bedrooms, fireplace living room; nice open concept. Eat in kitchen complete with a granite center island and countertops, as well as modern stainless steel appliances. The family room is highlighted by a cozy fireplace, while the dining room is tastefully appointed for formal gatherings. Beautiful hardwood floors throughot. Basement
About 21 Pleasant St #2, UPTON, MA 01568 -1) 2nd floor unit, 2) Surrounded by single family homes, 3) Fully de-Leaded. 4) Mins walk to Memorial Elementary School 5) 1/2 (half a mile) walk to Nipmuc Regional High School & Blackstone Valley Regional Vocational Technical High School, 6) Hardwood floors in all bedrooms 7) Unit Washer-Dryer hookups 8) Spacious front & backyard for pet owners, 9)
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