$2,302,687Average Value$573Average Price per Sq Ft11Homes 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.
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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.
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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.
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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.
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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.
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.
Crime and Safety
1 - Low Crime, 10 - High Crime
The Flats
US
Homicide
3
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
2
4
Motor Vehicle Theft
2
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
The Flats Demographics and Home Trends
On average, homes in The Flats, Winchester sell after 33 days on the market compared to the national average of 56 days. The median sale price for homes in The Flats, Winchester over the last 12 months is $2,350,000, up 9% from the median home sale price over the previous 12 months.
The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and
40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows.
Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal
Paula SughrueBetter Homes and Gardens Real Estate - The Shanahan Group
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
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are
Nancy PallottaGibson Sotheby's International Realty
Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a
A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry,
Nancy PallottaGibson Sotheby's International Realty
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and
Nancy PallottaGibson Sotheby's International Realty
Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all
Beautifully renovated 5 bedroom, 11 room home w 2 home offices located in the desirable FLATS area of town. An inviting front porch welcomes you into this special home showcasing the charm & character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear
Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves
Tucked within the coveted enclave of Graystone, this exceptional townhouse offers a rare blend of scale, privacy, and refined living. Among the largest residences in the community, this impeccably maintained 2-bedroom, 3.5-bath home unfolds across more than 3,800 square feet of thoughtfully designed space. Sunlight pours through expansive windows, illuminating gracious living and entertaining
Nancy PallottaGibson Sotheby's International Realty
TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/
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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.
