These are the highest-priced home sales reported in the Worcester, Massachusetts metro area for the week ending October 4, 2026. The five sales came to a combined $6.79 million.
Each sale was in a different town, from Berlin and Southborough to Westborough, Mendon and Upton, and all five were in Worcester County. The group runs from a farm established in the mid-19th century to a home finished this year, with Colonials from the 1990s and 2000s in between.
No. 1 — $1,800,000 · 187 Highland St, Berlin, Massachusetts
Highland Hill Equestrian Center, a horse property on Highland Street in Berlin, sold for $1,800,000, the highest price of the week.
The land is the heart of it. The property covers 12.88 acres of cleared farmland, level in parts and gently sloping in others, the largest lot in this Top 5. Its 20-stall barn has lounges that are both heated and air-conditioned, and an indoor riding arena measures 72 by 200 feet. Outside are a paddock, 20 individual turnouts and open fields for riding.
The home itself is an antique farmhouse built in 1850, the oldest of the five. It is a frame Colonial with four fireplaces, wood and tile floors, an office and a walk-up attic. It has four bedrooms and two bathrooms, one full and one half, in 2,544 square feet, and the property has garage space for four cars.
Kristin D’Amico of Bridge Realty was the listing agent, and Kerry Parker of Equine Homes Real Estate, LLC represented the buyer. The property went under contract 23 days after it was listed.
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No. 2 — $1,485,000 · 3 Graystone Way, Southborough, Massachusetts
In Southborough, 3 Graystone Way sold for $1,485,000. The home sits on a wooded 2.11-acre corner lot with stone walls and professional landscaping, one of 13 custom-built homes on a private way and cul-de-sac.
Built in 1997, the Colonial has 4,054 square feet, the most living space of the five, and five bedrooms, also the most. Its four bathrooms are three full and one half. A two-story foyer leads into a home office behind French doors, warmed by a wood-burning fireplace. The kitchen has maple cabinetry, Thermador gas cooking, a large breakfast island and a pantry, and it opens both to a patio and to a family room whose masonry fireplace has a gas insert. There is also an oversized dining room and a mudroom off the garage.
Four of the bedrooms and two full baths are on the second floor. The third floor is set apart as guest quarters, with its own family room, a bedroom and a full bath. The property last sold in 2014 for $875,000.
The home went under contract 14 days after it was listed. Kim Foemmel of Foemmel Fine Homes was the listing agent, and Ginny Martins of Ginny Martins & Associates represented the buyer.
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No. 3 — $1,205,000 · 23 Piccadilly Way, Westborough, Massachusetts
A Colonial in Westborough’s Piccadilly Mill neighborhood sold for $1,205,000 after going under contract seven days after it was listed. It sold above its asking price of $1.175 million.
The home was built in 1993 and last sold in 1994, for $323,751. It has four bedrooms and three bathrooms, two full and one half, in 3,675 square feet on 0.83 acres. The family room is the centerpiece, with a vaulted ceiling, skylights, a gas fireplace, custom built-ins and fruitwood trim. Formal living and dining rooms are finished with crown molding, hardwood runs through the main living areas, and the kitchen has quartz counters and stainless steel appliances. A heated atrium looks out over the private backyard.
Upstairs, the primary suite has a vaulted ceiling, a walk-in closet and its own bath, and an adjoining room with large windows and a cedar closet could serve as an office or nursery. The finished lower level has media, office and exercise rooms. Outside are a bluestone patio, a deck, mature plantings and stone walls, along with an oversized two-car garage.
Le Doan of eXp Realty LLC was the listing agent. Katelyn E. Sullivan of Coldwell Banker Realty – Boston represented the buyer.
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No. 4 — $1,200,000 · 14A Lundvall Rd, Mendon, Massachusetts
The newest home in this Top 5, and its only new construction, is on Lundvall Road in Mendon’s Spring Brook subdivision. Completed in 2026, it sold for $1,200,000 and sits on 10.15 acres.
The home has three bedrooms and three bathrooms, two full and one half, in 2,799 square feet. The primary suite is on the main level, with a private full bath and two walk-in closets. The rest of that floor is open, with a kitchen and pantry, living and dining areas, a study and a half bath. A family room with a fireplace leads to an enclosed porch, and there is a deck as well. Two more bedrooms upstairs share a full bath, and a living area sits over the three-car garage.
The walk-out lower level is roughed in for another bedroom, a full bath and a half bath. The home has three laundry hookups in all, and its driveway is shared with one neighboring home.
The home went under contract seven days after it was listed and sold just above its asking price. Lawney Tinio of Century 21 Custom Home Realty was the listing agent.
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No. 5 — $1,100,000 · 33 Dairy Dr, Upton, Massachusetts
On Dairy Drive in Upton’s Preserve at Lake Wildwood, a 2004 Colonial sold for $1,100,000. Its wooded 1.02-acre lot, professionally landscaped and fenced, borders trails and conservation land, and a composite deck and a patio look out over a fish pond. There is a shed for storage, along with a sprinkler system and decorative outdoor lighting.
Inside, the main floor is open. A large family room with a fireplace joins a kitchen with a double oven, a five-burner gas cooktop and an oversized island, and a custom wet bar has a wine fridge. A private office has crown molding and French doors, and the first floor also has a living room, a dining room and laundry. Upstairs, the primary suite has walk-in closets, and all four bedrooms have hardwood floors. The home has three bathrooms, two full and one half, in 3,360 square feet, with a side-facing two-car garage.
The property last sold in 2023 for $1.065 million. This time it went under contract 23 days after it was listed, with Erika Steele of REMAX Executive Realty as the listing agent and Sara Pellegrini of Afonso Real Estate representing the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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See full market data on our Worcester Metro Area market page.
