The five highest-priced home sales reported in the Worcester metro area for the week ending October 18, 2026, came from five towns: Boylston, Southborough, Webster, Shrewsbury and Bolton. Together they totaled $8.01 million.
All five are single-family homes built between 1983 and 2017. The list runs from a 1980s contemporary with a river view to a lakefront home finished less than a decade ago, and the last two places on it are shared by a pair of Colonials that each sold for $1,275,000.
No. 1 — $2,085,000 · 5 Redwood Cir, Boylston, Massachusetts
The top sale of the week was a contemporary in Boylston designed by Masiello, a home where the architecture is the point. It sold for $2,085,000. Built in 2013 on a cul-de-sac, it sits on 4.46 acres that border a private golf course and the home has views of the course.
The design pairs midcentury modern lines with interiors drawn from Asian traditions, and the landscape is the work of Zen Associates. Large expanses of glass are framed in black aluminum-clad wood windows and doors, and custom walnut millwork runs through the rooms. The kitchen is built around an island with a waterfall edge and opens to the dining and living areas. An elevator reaches every level, the home has whole-house shading and sound wiring, and there is a wet bar.
The home has four bedrooms, three full baths and two half baths in 3,243 square feet, along with two fireplaces, one of them in the living room. Outside are terraces, a covered patio, a garden, stone walls and specimen plantings, and the heated, oversized garage has room for three cars.
Michael Carucci of Serhant was the listing agent. Lisa A. Bradley of Coldwell Banker Realty – Worcester represented the buyer.
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No. 2 — $1,775,000 · 6 Lynbrook Rd, Southborough, Massachusetts
In Southborough, a custom contemporary on a 1.60-acre corner lot along the water sold for $1,775,000, the second-highest price of the week. Built in 1983, it is the oldest of the five homes and, at 7,483 square feet, the largest. It has been renovated throughout, and the property last sold for $875,000 in 2004.
The primary suite is on the first floor, set apart, with its own office, a walk-in closet and a renovated bath. Three more bedrooms are on the upper floor, for four in all, and the home has four full baths and a half bath. The kitchen was redone with high-end cabinetry, counters and appliances, and there are three fireplaces.
The lower level works as a second living space, with large windows, an exercise room, a game area, an office, a full second kitchen and space for a home theater. The home also has a loft, a library and a media room.
The grounds look out on the Sudbury River. There is a heated in-ground pool, a hot tub with a cabana and a putting green, and a separate accessory dwelling has been fully renovated. The attached garage holds four cars.
Jeffrey Incutto of BA Property & Lifestyle Advisors was the listing agent, and Nova Group of Hooli Homes Boston represented the buyer.
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No. 3 — $1,600,000 · 24 Laurelwood Dr, Webster, Massachusetts
The newest home in the Top 5 is a Craftsman on Webster Lake in the Laurelwood neighborhood of Webster, built in 2017. It sold for $1,600,000. The property last sold for $410,000 in 2013, before the current home was built.
The home was designed around the water and its views to the west, which are framed by an architectural tower. The main level has an open plan joining the kitchen, dining area and living room, and the living room leads both to a large deck and to a bright sitting room. The primary suite includes a full bath with a double vanity, a walk-in closet and a dressing room.
On the lower level, a second full kitchen and a large recreation room open onto a patio by the lake, and two more bedrooms and a bath are on that level. The home has three bedrooms, two full baths and a half bath in 3,790 square feet.
The sloped 10,880-square-foot lot has private frontage with direct access to the lake. Outside are decks on several levels facing the water, a curved stone-faced patio, a cabana and terraced landscaping with its own waterfall.
Sharon Pelletier of Hope Real Estate Group, Inc. listed the home with Bryan Pelletier, and Sharon Pelletier also represented the buyer, putting the same agent on both sides of the sale.
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No. 4 — $1,275,000 · 28 Hickory Dr, Shrewsbury, Massachusetts
The home at 28 Hickory Drive in Shrewsbury went under contract 16 days after it was listed and sold for $1,275,000, above its asking price of $1.249 million. The 2010 Colonial is in Hickory Hill Estates, on a level 0.57-acre lot lined with trees. The property last sold for $599,000 in 2010.
A two-story foyer opens into a main level with 9-foot ceilings, a private office, a living room, a dining area and a kitchen with a breakfast nook that steps out to the deck. Laundry is on the first floor. The four bedrooms are upstairs, among them a primary suite with its own bath and a walk-in closet, and the home has two full baths and a half bath in 3,582 square feet. A lower-level recreation room, a fireplace, an EV charger and a two-car garage round it out.
Yang Liu of Weston Realty LLC was the listing agent with Shourui Tian. Sagar Shah of Sagar Shah Realty Group LLC represented the buyer.
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No. 5 — $1,275,000 · 293 Wattaquadock Hill Rd, Bolton, Massachusetts
Matching the Shrewsbury sale at $1,275,000, a 2014 Colonial on Wattaquadock Hill Road in Bolton sits on the largest lot of the five, 4.50 level acres with professional landscaping. It went under contract 21 days after it was listed and sold at its full asking price. The property last sold for $848,000 in 2014.
The home has four bedrooms, two full baths and a half bath in 3,388 square feet, with an open floor plan, hardwood and tile floors and a fireplace in the living room. The primary bedroom has its own bath. An enclosed porch, a full basement and an attached three-car garage complete the home.
Jane O’Connor of Coldwell Banker Realty – Worcester was the listing agent, and Karen Shattuck of Lamacchia Realty, Inc. represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 18, 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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