$2,375,471Average Value$603Average Price per Sq Ft8Homes For Sale
Grand homes next to Winchester's town center
West of Winchester’s town center, the rolling hills of Massachusetts level out and fold into a residential neighborhood called The Flats. The hamlet offers a slice of luxurious suburban living less than 10 miles north of Boston. Its streets are lined with grand homes, many set on modest lots with neatly landscaped lawns. Along with upscale living, The Flats also offers proximity to Winchester’s vibrant downtown district and access to top-performing schools, making the neighborhood a sought-after corner of suburban Boston.
Traditional home styles imbue an established feel
Tucked underneath a lush canopy of trees, the traditional homes of The Flats create an established feel. Colonial-revival homes are most common, with crisp white or brick facades and classic black shutters. English Tudors, Dutch colonials and a few Victorian-style homes are sprinkled in to the mix. The median listing price for homes hovers around $2.3 million. Luxury condos range between $720,000 and $990,000, while townhouses and duplexes can be between $900,000 and $1.6 million. Single-family homes typically start around $1.3 million and can fetch up to $4.8 million, depending on size and location.
Tudor style homes are a popular option for home hunters within The Flats neighborhood of Winchester.
Manicured lawns and homes that sit back off the street can be found all throughout The Flats neighborhood.
1/2
Top-rated Winchester schools with high rankings
Winchester Public Schools serves students living in The Flats and is often lauded for its top ratings. The district, ranked the seventh-best in Massachusetts, earns an A-plus rating from Niche. Children may start at A-rated Ambrose Elementary before advancing to McCall Middle School. Serving more than 1,300 students, Winchester High School prides itself on high test scores and high ratings for teachers and academics. The middle and high schools each boast an A-plus from Niche. Nearby private schools include the A-plus-rated Phillips Academy Andover, which Niche ranks as the second-best private school in the United States.
Winchester High School has an A+ rating on Niche.
Ambrose Elementry School in Winchester has an overall grade of B on Niche.
1/2
Recreational spaces include athletic fields and state parks
The Flats is surrounded by vast beaches, nature preserves and athletic facilities. The area’s many lakes and ponds allow for swimming, fishing and boating. Mystic Lakes State Park is home to Shannon Beach. At the 120-acre Whipple Hill Nature Preserve, nature lovers can explore 4 miles of trails. The Tri-Community Greenway leads from the town center to Ginn Field, a recreational area with a playground and ball fields. Pocket parks, such as Middlesex Park and Elliot Park, offer a corner of green for walking the dog, a picnic or a game of catch. And nearby country clubs allow golfers to perfect their swing.
The Mystic River Reservation invites locals to peer at its beautiful crystal stream.
The Stone Family Playground at Ginn Field in Manchester, MA.
1/2
Local shopping and dining in Downtown Winchester
Train tracks bisect Downtown Winchester, which butts up against The Flats’ east side. The central district features old-charm brick buildings that house an amalgam of locally owned stores, businesses and restaurants. Above brick sidewalks, flowers adorn traditional street lamps. The Book Ends shop is hard to miss, thanks to its location in a Victorian-style corner building. Favorites for dining include Lucia Ristorante, loved for its family-style Italian dishes and old-country décor, and Black Horse Tavern, an equally cozy pub with an inviting atmosphere. Other dining options range from Mediterranean to Chinese. Nearby grocery stores include Stop & Shop and Whole Foods Market.
Grab a tasty bite at Black Horse Tavern in the Flats for either lunch or dinner.
Lucia is a popular restaurant serving up Italian comfort dishes near The Flats neighborhood.
1/2
Reaching Boston by train or car
Train tracks run along the neighborhood’s east side, punctuated by the Winchester Center and Wedgemere train stations. Both are served by the Lowell train line, which connects to Boston’s West End. Drivers rely on Interstate 93 to get to the heart of Boston; the nearly 10-mile drive takes roughly 15 minutes in average conditions. Boston Logan International Airport is also about 10 miles away.
Written By
Christina von Claparede-Crola
Photography Contributed By
Noel Poage
Video By
GL Moses
Was this overview helpful?
Agents Specializing in this Area
Catherine Albiani
Better Homes and Gardens Real Estate - The Shanahan Group
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 The Flats neighborhood?
to let others know what life in this neighborhood is like.
The Flats Demographics and Home Trends
On average, homes in The Flats, Winchester sell after 27 days on the market compared to the national average of 53 days. The median sale price for homes in The Flats, Winchester over the last 12 months is $2,385,000, up 45% from the median home sale price over the previous 12 months.
Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized
Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The
Andersen Group RealtyKeller Williams Realty Boston Northwest
This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard
Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering
Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end
Joan Francis SullivanBetter Homes and Gardens Real Estate - The Shanahan Group
Wonderful opportunity to rent in Winchester, less than a half mile from the town common. Rarely available First floor unit with hardwood floors throughout, 2 bedrooms and one full tiled bath. Additional storage space in lower level that is wired to your specific unit...could be used for office space, home gym, craft room, etc. Carefree living with Heat, basic cable tv and all exterior maintenance
Catherine Albiani
Better Homes and Gardens Real Estate - The Shanahan Group
This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for 11-02-2025.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was
Location, Location, Location!! This beautifully updated 2 bedroom 2.5 bath conveniently located in Winchester Center. Recently renovated, this unit boasts a stunning kitchen with farmer sink, high end stainless appliances, custom cabinetry and pantry. First floor offers living room w/ fireplace and large dining room with hardwood throughout. 2 spacious bedrooms and 1.5 baths complete the second
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
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.