Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Southborough is known for
Southborough is a small town at the eastern edge of Worcester County, about 25 miles west of Boston. It is known for the Sudbury Reservoir and its trails, two historic private schools on Main Street (St. Mark's School and Fay School), and four historic villages: Downtown, Cordaville, Fayville and Southville. Route 9, the Mass Pike and I-495 all pass through town, and the MBTA commuter rail stops in Cordaville.
Southborough was the south part of Marlborough, long called Stony Brook, until the Massachusetts General Court incorporated it as its own town on July 17, 1727. The first town meeting was held a week later at Timothy Brigham's house, where St. Mark's School stands today. In the 1890s Boston's Metropolitan Water Works dammed Stony and Angle Brooks to create the Sudbury Reservoir, putting much of the northeast part of town under water, and the town celebrates its Tricentennial in 2027. Southborough feels rural and quiet, with stone walls, farm fields, conservation land and a classic town center with a green, Town House and churches. Many residents commute to Boston, Worcester and the I-495 office corridor by car or by train from Cordaville.
Where to live
The village at the geographic center of town along Main Street (Route 30). It holds the Town House, Community House, library, post office, churches, a town green, and the Fay School and St. Mark's School campuses. The Southborough Center Historic District is listed on the National Register. (source)
Village in the east end that grew up where the Boston and Worcester Turnpike (Route 9) met Central Street and Oak Hill Road. Route 9 runs through the middle with mixed businesses, while the area south of Route 9 along Oak Hill Road is mostly residential. Many streets look out on the Sudbury Reservoir, and Fayville keeps its own post office and 01745 zip code. (source)
A 19th century mill village in the southwest corner of town. Former mill worker houses still line Parker Street, Cottage Street, Cordaville Road and Southville Road, mixed with older homes and newer construction. It is home to the MBTA commuter rail station and is popular with Boston commuters. (source)
A second 19th century mill village west of Cordaville along Southville Road, where boots, shoes, cotton and woolen goods were once made. Housing is a varied mix tied to its industrial past, with St. Matthew's Church and the Old South Union School nearby and a small artisan community. (source)
Most of Wolf Pen Farm was sold at auction in 1975, and it became several subdivisions of large houses on large lots on both sides of Sears Road in the north part of town. (source)
Deerfoot Farm, home of the Deerfoot dairy, closed in 1969. Much of its land between Main Street and Route 9 was then divided for new homes. (source)
The largest mid-century subdivision in town. Several streets south of Richards Road were built up in the 1960s with ranch and split-level houses in a few basic designs. (source)
Local favorites
Locally owned Irish restaurant and pub with in-house brewed beers, two floors and two bars, plus live music nights. (source)
A breakfast and lunch spot with roots back to 1946, now run by the Mauro family with executive chef Dean Lewis. It serves scratch-made comfort food and has a deli counter. (source)
Family owned since 1974 by the Baltas family, now in its third generation, and located in the town's renovated Old Fire Station since 1984. (source)
Handcrafted margaritas, tacos, fajitas and seafood, with birria tacos a customer favorite. It also serves weekend brunch. (source)
Chef-prepared meals made with locally sourced ingredients, with a drive-thru for mobile orders. Opened in Southborough in August 2022. (source)
Asian fusion kitchen with sushi and a bar. (source)
Large menu of pizza, calzones, subs, burgers and fitness bowls, known for party-sized pizzas. (source)
Takeout and delivery spot for pizza, sandwiches and Greek dishes. (source)
After hours
The town library at 25 Main Street in the town center. (source)
Public 9-hole course at 36 Cordaville Road with a clubhouse, small pro shop and snack bar serving beer and wine. (source)
Gallery run by three local artists that hosts exhibits, art classes and events, plus an annual holiday shop in November with vendors and food trucks. (source)
Beer hall and beer garden at 100 Clinton Street in Framingham pouring fresh Jack's Abby lagers with wood-fired pizza. (source)
Brew pub at 66 Otis Street in Westborough with house-brewed beers, a full restaurant and event space. (source)
Shopping
Local florist and greenhouse at 40 Mt. Vickery Road selling flowers, plants and gifts. (source)
Family farm at 30 Jericho Hill Road with cut-your-own Christmas trees, holiday decor, ornaments, honey and candles. (source)
Wine, spirits and gifts shop that also makes sandwiches, soups and salads, at 154 Turnpike Road. (source)
Large regional shopping center on Route 9 in Framingham with stores such as Best Buy, Nordstrom Rack, TJ Maxx, Marshalls and an AMC theater. (source)
Enclosed shopping mall at 601 Donald Lynch Boulevard in Marlborough. (source)
Outdoors
About 5 miles of trail along the reservoir from Framingham Road west to the Westborough line, with fishing spots, a boulder island and sunset views. (source)
A 90-acre property of rolling hills, grassy trails and wide open views, good for picnics and birdwatching. Leashed dogs are welcome. (source)
Nearly 60 acres of former farmland south of Main Street owned by the Southborough Open Land Foundation, with meadows, a pond, pine woods and trails over the Wachusett Aqueduct channel. (source)
A 170-acre working farm run by The Trustees, with stone-walled fields, a cart path into the woods, grassland bird reserves and farm programs. (source)
A 1,500-acre state park with two seasonal swimming beaches, more than 10 miles of trails, boating and picnic areas. (source)
Over 800 acres with 7 miles of marked trails for hiking, horseback riding and mountain biking. (source)
Over 2,000 acres on former Army land, with the main entrance on Winterberry Way off Hudson Road in Sudbury and more than 15 miles of trails for hiking, biking, fishing and cross-country skiing. (source)
Things to do
The Southborough Historical Society's home in the restored 1911 Fayville Village Hall, with history and arts programs, storytelling nights, music and classes. (source)
Episcopal church founded in 1860 by Joseph Burnett, built just west of the Southborough Town House after 1862. (source)
Part of Boston's historic water system, a three-mile open channel built in the 1890s by widening a brook to carry Nashua River water into the Sudbury Reservoir. (source)
Hopkinton Center has hosted the start of the Boston Marathon since 1924. Crowds gather on race morning in April. (source)
Native Plant Trust botanic garden at 180 Hemenway Road with more than 1,000 species of New England native plants on 45 acres. (source)
On the calendar
Town celebration on St. Mark's Field at Routes 30 and 85 with a morning parade and booths for crafters, nonprofits, food trucks and local businesses. (source)
Free Halloween event outside Woodward School put on by the Southborough Firefighters Association and Southborough Recreation. (source)
Juried outdoor art show at Beals Preserve by the Southborough Open Land Foundation, ending with a poetry reading and art walk. (source)
Events marking 300 years since the town's 1727 incorporation, organized by the Tricentennial Committee. (source)
Watch the start of the Boston Marathon in neighboring Hopkinton Center. (source)
Schools
Mary E. Finn School (PreK-1), Albert S. Woodward Memorial School (2-3), Margaret A. Neary Elementary School (4-5)
P. Brent Trottier Middle School (6-8)
Algonquin Regional High School (Northborough), Assabet Valley Regional Technical High School (Marlborough)
Fay School (PreK-9), St. Mark's School (9-12)
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
I-495, I-90 (Mass Pike), Route 9, Route 30 and Route 85
Worcester Regional Airport, about 30 min; Boston Logan International, about 40 to 60 min depending on traffic; Providence T.F. Green, about 1 hr
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.