Holliston is a small Boston suburb with a highly rated school system, beloved local businesses and a diverse housing stock. “It really has a Norman Rockwellian feel,” says Executive Partner, Lauren Davis with Realty Executives Boston West, who has about 20 years of experience in the area. Home to a neighborhood named Mudville and several other connections to the famous poem, "Casey at the Bat,” the community takes pride in its role in Boston’s deep-rooted baseball history. The town also has a CAP Index crime score of 1, which is significantly lower than the national average of 4. Holliston’s location 23 miles southwest of Downtown Boston attracts homebuyers seeking a historic, slower-paced town with classic New England architecture.
Supporting small businesses in Holliston
Holliston’s downtown area along Central and Washington Streets houses the town’s most frequented businesses. Casey’s Pub, a nod to “Casey at the Bat,” serves slow-smoked chicken wings and an array of pub fare. Casey’s occasionally hosts live music and caters to sports fans looking to catch a game on live TV. Coffee Haven, another locally owned spot, is as much of a gathering place as it is a restaurant. Holliston Superette serves as the area's go-to for custom-cut meats, deli items and fresh seafood. “They even have a few everyday essentials in case you run out of something,” Davis says. Residents often stop by and say hello to John, the owner of Fiske’s General Store, a town staple since the 1800s. “It’s such a fun place to shop,” Davis says. “The local kids pick up gifts here, and the owner celebrates residents’ birthdays with posters on the store door.” Although the town tends to favor small businesses, a CVS sits off Central Street, and Shaw’s and Market Basket are within about 4 miles. Target, Stop & Shop, retail and chain options are also available about 6 miles southwest in Milford.
Holliston’s events, parades and steam engine train rides
Although Holliston embodies a rural atmosphere, the community comes together for various events throughout the year. The town celebrated its 300th birthday with a parade in May of 2024, complete with floats, live music and marching bands. The Holliston Newcomers & Neighbors Club is one organization that coordinates fundraisers and activities, including the Great Pumpkin Trail Walk, book clubs and putting together Easter baskets for the local Food Pantry. The Waushakum Live Steamers club meets from May through October and hosts events where visitors, often children, can ride steam locomotives. With an active historical society, Holliston's residents can learn about the area's past and attend events, including model train shows, which partner with the Waushakum Live Steamers, and the fall Harvest Fair, known for its local vendors and artists.
Getting outside and active in Holliston
Holliston has plenty of outdoor gathering spaces and parks, including Lake Winthrop, which features two public beaches often used for kayaking and paddleboarding. Hikers can head to the Upper Charles Rail Trail, which runs 13.2 miles and connects several towns. “People walk, bike and ride their horses here,” Davis says. This trail also cuts through Blair Square, which is a local gathering area with benches and green space that hosts the seasonal farmers market. Brentwood Conservation Land is another outdoor recreation option, offering 400 acres of wildlife trails and ponds. Pinecrest Golf Club sits nearby and is open for public tee-times.
Highly rated Holliston Public Schools
The Holliston Public Schools district earns an overall A-minus grade on Niche and consists of four schools. Sam Placentino Elementary School, for students in prekindergarten through second grade, scores a B grade. Third through fifth graders can enroll at Fred Miller Elementary School, which has an A-minus. Robert Adams Middle also scores an A-minus and offers a variety of extracurricular activities, including jazz band, debate club and ultimate frisbee. At Holliston High School, which earns an A, students can participate in over 20 athletic teams, including alpine skiing and gymnastics. The school district also offers a Montessori program that begins in preschool and continues through fourth grade. “It’s very popular, and there are only two in the state,” Davis says. “The traditional program is fantastic here, too.”
Holliston’s quintessential New England housing market
Holliston’s housing stock includes antique colonials, Cape Cods, ranch styles and some new construction. Many properties, whether in subdivisions or located off rural roads, tend to come with a lot of land. Three-bedroom homes tend to start around $550,000, while those with four-to-five bedrooms can climb past $1 million. Homebuyers can find 19th- through 21st-century properties and unique living options, including senior, golf course and equestrian communities. Some streets feature sidewalks, while other residential areas are secluded and private, catering to various social and walkability preferences.
Transportation and accessibility to various facilities near Holliston
The closest commuter rail is about 6 miles north in Ashland on the Framingham/Worcester Line. MetroWest Regional Transit Authority bus stops are also available along Washington Street. Holliston sits within about 6 miles of Interstate 495, as well, leading to Interstate 90, which flows into Boston. For longer trips, Boston Logan International Airport is about 32 miles away via I-90. Residents have access to health care within 20 minutes via Washington Street and Western Avenue at MetroWest Medical Center. While the closest synagogues and Islamic centers sit outside of the neighborhood within about 6 miles, many Christian churches of various denominations are located in the area.
Tony Mallozzi is a lifelong resident of Central Massachusetts, having grown up in Northborough, MA. He is a proud alum of Fay School in Southborough and graduated from Cushing Academy in Ashburnham. Tony earned his Bachelor of Arts in Economics with a minor in Business Administration from the University of Connecticut, where he also played baseball for the Huskies.
Tony began his real estate career at RE/MAX, working in their Northborough office from 2005 to 2010. During his time there, he was a nationally recognized, top-producing agent for four consecutive years. In 2010, he founded Anthony Joseph Real Estate LLC, where he continues to leverage his extensive experience and industry knowledge.
A proud member of the National Association of Realtors (NAR), Tony is known for his ability to build and maintain strong client relationships while delivering creative, client-focused service. His approach centers on understanding and prioritizing his clients’ needs and goals.
Tony was recently recognized as one of the top 20 brokers in the MetroWest/Central Massachusetts region by Boston's Top 20. He has personally sold over 750 homes in Massachusetts and is also a licensed broker in New Hampshire.
Outside of work, Tony is a proud member of Worcester Country Club and enjoys spending time with his wife and two children in Shrewsbury, where the family resides.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
