$1,785,406Average Value$529Average Price per Sq Ft12Homes For Sale
The wooded suburbs to the west of downtown
Winchester is a small town just north of Boston where the idea of separate neighborhoods likely doesn’t occur to long-time residents. “Winchester is a small town, with a nice community feel that really sets it apart,” says Realtor Catherine Albiani, broker with Better Homes and Gardens Realty who has lived in the area for almost 20 years. “The school system is good and there are highlights like the photography museum that you wouldn’t expect to find here.” The West Side of town, separated from the central district by a two-lane highway, is defined by residential streets that wind beneath tall trees and along the banks of Mystic Lake. A popular country club and several boat clubs help complete the picture, as do the many trails that weave through preserved woodland and up the tallest point in town. Yet although the West Side presents more the sylvan facet of the town’s makeup, those who live in Winchester consider all of it their neighborhood.
An overview of the West Side neighborhood's large single family homes in Winchester, MA.
You can learn to sail at the Winchester CC Boat Club in the West Side neighborhood.
1/2
Continuous construction, from the 1920s till today
Homes on the West Side sit on lots that are often shaded by dense patches of woodland, with large front and back lawns. The houses reflect architectural sensibilities of the early- to mid-20th century. Colonials from the 1920s and 1930s sit just a few yards down from midcentury Cape Cods, ranch-styles and split-levels, towered over by neighboring Modern Traditional builds constructed between 2015 and 2024. Two-unit townhouses on the south side of the neighborhood complete the picture. Nearly all homes feature driveways that set them back from winding webs of suburban streets. There are no sidewalks, so neighbors walk their dogs along the slightly raised curbs. Townhouses range in price from around $850,000 to over $1 million. Prices for detached single-family homes begin around $1 million and can rise to over $4 million depending on build year, number of bedrooms and size of the lot.
A row of homes including a Colonial Revival styled in West Side of Winchester, MA.
A brand new, Modern Traditional styled home in the West Side neighborhood of Winchester, MA.
1/2
The well-regarded Winchester Public Schools
The Winchester Public School district is very well-regarded, ranking in Niche’s Top 10 for the state of Massachusetts. Vinson-Owen Elementary sits in the center of the West Side neighborhood, walkable from the nearest cul-de-sacs and home to the Vinson-Owen Science Park, an educational green space on school grounds. McCall Middle, in the heart of Winchester, is the closest public middle school, and Winchester High is likewise the closest public high school. All three institutions receive an A-plus rating from Niche. Lexington Christian Academy is a private day and boarding school just outside the neighborhood, which has served students in grades 6 through 12 since it opened in 1946. The Academy also scores an A-plus.
McCall Middle School is right in the city center of Winchester and nearby the West Side.
Winchester High School's is nearby to the West Side and an A-plus rating from Niche.
1/2
The tallest point in all of Winchester
Several backyards in the West Side open on Mount Pisgah, the highest point in Winchester. The trailhead is accessible from Andrews Road, and residents can follow its winding way up the 350-foot incline, observing many unique wildflowers along the way. There is an old water tower at the woodland’s center, but hikers should avoid it as it is encircled by poison ivy. Nearby Whipple Hill boasts a more extensive trail system where pet owners may allow their trustworthy dogs to roam off-leash beside them. Golfers will prefer to get their exercise on the Winchester Country Club’s 18-hole course, planned by famed designer Donald Ross. Local anglers can head to Upper Mystic Lake to cast their lines and enjoy a tranquil fishing trip, though they will want to avoid Shannon Beach, which tends to be a popular destination for families looking to splash about on summer days. Adventurous cyclists are not left out of the fun. “The Minuteman Commuter Bikeway runs from Mystic Street all the way through Lexington,” Albiani says. This 9-mile trail can be picked up at many places along the way, including Arlington’s Great Meadows. “It sounds pretty intense, but it doesn’t have to be,” Albiani adds. “It’s pretty flat.”
You can access the Whipple Hill Nature Reserve from Winchester's West Side neighborhood.
The Winchester Country Club is a membership club in the West Side neighborhood.
1/2
Between Boston and Burlington
The Whole Foods at Horn Pond Plaza in Woburn is the closest supermarket to the West Side, just 3 miles from most homes. The Market Basket and the H-Mart in Burlington are 4 miles north as well. There is a Target at the Burlington Crossroads shopping center, just one block south of Atrius Health Medical Center. Gardeners can pick up supplies at Mahoney’s Garden Center without having to leave the neighborhood. Burlington Mall is less than 5 miles up Middlesex Turnpike, home to over 185 retailers and restaurants, ranging from upmarket national staples like Legal Seafood to homegrown local chains like Frank Pepe Pizzeria, famous for their New Haven-style white clam pies. Downtown Winchester has developed into a popular shopping destination as well. “There are lots of nice boutiques and great restaurants there,” Albiani says. “It’s a great place to walk around and grab a unique gift. Our chamber of commerce is amazing and always looking for ways to boost desirability.”
Residents can find a Whole Foogs Market close by to West Side neighborhood of Winchester, MA.
For fresh and local produce, visit Mahoney's Farmstand in the West Side neighborhood.
1/2
The Lowell Line to downtown
Route 3 traces the eastern edge of the neighborhood, running north of the West Side 4 miles to Burlington and south 5 miles to the outskirts of Boston. This road affords residents access to Interstate 95, the effective boundary between Lexington and Burlington to the north. I-95 is, of course, infamous for its backups, but public transportation is readily available. Wedgemere train station is the closest to the neighborhood, where locals can catch the Lowell Line train and arrive at North Station in the heart of Boston within roughly 20 minutes. When looking to get out of town, Logan International Airport is about a 14-mile drive southeast via Interstate 93.
You can take the commuter rail to Boston from the Wedgmere or Winchester Center stations.
An aerial from Winchester's West Side of Route 3 towards Boston, MA.
1/2
Spirit Weekend in central Winchester
While Winchester is a quick train ride from everything happening in Boston, residents do not need to venture far from home to experience the spirit of Massachusetts. “Downtown is always doing community events,” Albiani says. “Right now, it’s Spirit Weekend, so the high school football team goes through the center of town and the shops are all offering discounts. I’m sponsoring a beer garden at the Arthur Griffin Photography Museum soon, which is a great little spot that you wouldn’t even know it’s there unless you’ve been there.”
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.
View GreatSchools Rating Methodology
Are you familiar with the West Side neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
West Side
US
Homicide
3
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
1
4
Motor Vehicle Theft
1
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
West Side Demographics and Home Trends
On average, homes in West Side, Winchester sell after 23 days on the market compared to the national average of 58 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,627,000, down 1% from the median home sale price over the previous 12 months.
Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless
Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated
Paula SughrueBetter Homes and Gardens Real Estate - The Shanahan Group
Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to
George SarkisDouglas Elliman Real Estate - The Sarkis Team
Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz
Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept
Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England
15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The
Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.
Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open
Catherine AlbianiBetter Homes and Gardens Real Estate - The Shanahan Group
Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.
Felicity TuttleBetter Homes and Gardens Real Estate - The Shanahan Group
This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is
Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds
New construction 6 bedrooms and 7 full baths, 2 Car garage. Located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry,
Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and
The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just
Stunning 2020-built residence, fully furnished, beautifully maintained and located atop a hill on the West Side of Town, proudly situated on over an acre of land and offering gorgeous panoramic views. 5 bedroom 4.5 bath, 5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-end appliances, oversized
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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.
