10

The Flats Homes for Sale

Section Image
  • 5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    /39

    $3,599,000

    • 6 Beds
    • 4.5 Baths
    • 5,876 Sq Ft

    5 Stratford Rd, Winchester, MA 01890

    This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

    Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /41

    $2,899,000

    • 7 Beds
    • 5.5 Baths
    • 5,864 Sq Ft

    10 Sheffield Rd, Winchester, MA 01890

    This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

    Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /39

    $3,249,000 Open Sat 1PM - 2PM

    • 6 Beds
    • 6.5 Baths
    • 6,028 Sq Ft

    44 Cabot St, Winchester, MA 01890

    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 Realty Keller Williams Realty Boston Northwest

    44 Cabot St, Winchester, MA 01890
  • 54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    /42

    $2,975,000

    • 6 Beds
    • 3.5 Baths
    • 5,238 Sq Ft

    54 Wedgemere Ave, Winchester, MA 01890

    Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring

    Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
  • 58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    /39

    $2,195,000

    • 6 Beds
    • 5.5 Baths
    • 5,791 Sq Ft

    58 Bacon St, Winchester, MA 01890

    Timeless elegance spans four meticulously finished levels with 15 rooms, 6 bedrooms and 5+ bathrooms(2 en-suite). Living room flows seamlessly into a sunroom for a perfect retreat. The dining room opens to a covered porch with a gas line for the grill. New, top shelf, chef’s kitchen with all the bells & whistles and open to the family room. Thoughtfully designed for convenience, an elevator from

    Real Estate Advisors Group Coldwell Banker Realty - Belmont

    58 Bacon St, Winchester, MA 01890
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /35

    $2,399,000

    • 6 Beds
    • 5 Baths
    • 3,728 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combination of luxury, comfort, and convenience. Just minutes from Winchester Center, this beautifully crafted home places top-rated schools, boutique shopping, and vibrant dining right at your doorstep. Meticulously designed with high-end finishes throughout. Features include an

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Ivy Cir, Winchester, MA 01890
  • 9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    /42

    $3,895,000

    • 6 Beds
    • 3.5 Baths
    • 4,484 Sq Ft

    9 Lakeview Terrace, Winchester, MA 01890

    LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

    Kim Covino Compass

    9 Lakeview Terrace, Winchester, MA 01890
  • 107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    /42

    $2,499,000

    • 6 Beds
    • 4.5 Baths
    • 5,824 Sq Ft

    107 Cambridge St, Winchester, MA 01890

    Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

    Maija Sawyer Puleo William Raveis R.E. & Home Services

    107 Cambridge St, Winchester, MA 01890
  • 40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    /42

    $3,999,000 Open Thu 5PM - 7PM

    • 6 Beds
    • 4.5 Baths
    • 6,367 Sq Ft

    40 Foxcroft Rd, Winchester, MA 01890

    An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

    Monte Marrocco Coldwell Banker Realty - Lexington

    40 Foxcroft Rd, Winchester, MA 01890
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /38

    $2,499,000 Open Sun 12PM - 1:30PM

    • 7 Beds
    • 5.5 Baths
    • 4,829 Sq Ft

    89 Wildwood St, Winchester, MA 01890

    Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

    Monte Marrocco Coldwell Banker Realty - Lexington

    89 Wildwood St, Winchester, MA 01890
Massachusetts Winchester The Flats

Real Estate & Homes for Sale in The Flats, Winchester

Why Live in The Flats
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. 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. While the median price for real estate hovers around $1.7 million, prices may range from $740,000 up to $4.8 million. 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
Learn more about living in The Flats

Frequently Asked Questions

Is The Flats a good place to live?
The Flats is a good place to live. The Flats is considered car-dependent and bikeable. The Flats has 2 parks for recreational activities. It has a median age of 46. The average household income is $208,044 which is above the national average. College graduates make up 78.7% of residents. A majority of residents in The Flats are home owners, with 15.9% of residents renting and 84.1% of residents owning their home. A local real estate agent serving The Flats can help you decide if this neighborhood is the right one for you. Learn more on our The Flats neighborhood guide.
How much do you need to make to afford a house in The Flats?
The median home price in The Flats is $501,249. If you put a 20% down payment of $100,200 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in The Flats. The average household income in The Flats is $208K.
What are the best public schools in The Flats?
The best public schools that serve The Flats are:
What are the best private schools in The Flats?
The best private schools that serve The Flats are:
  • Acera School has an A- Niche grade, a student teacher ratio of 4:1 and an average review score of 4.4.
  • Saint Raphael School has a student teacher ratio of 13:1 and an average review score of 4.3.
  • St. Mary's School has a student teacher ratio of 19:1.
What are the most popular zip codes in The Flats, Winchester, MA?
The most popular zip codes in The Flats, Winchester, MA include 01890, 01801, 02474, 02155 and 02420.
What are the most popular neighborhoods near The Flats, Winchester, MA?
The most popular neighborhoods near The Flats, Winchester, MA are West Side, North Main, Symmes Corner, Grove Street and Winchester Highlands.
Are home prices dropping in The Flats?
Yes, home prices in The Flats are down 46% in the last 12 months.

Home Trends in The Flats, MA

On average, homes in The Flats, Winchester sell after 64 days on the market compared to the national average of 70 days. The median sale price for homes in The Flats, Winchester over the last 12 months is $512,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$512,000
Median Single Family Sale Price
$512,000
Average Price Per Sq Ft
$232
Number of Homes for Sale
1
Last 12 months Home Sales
16
Months of Supply
0.80
Median List Price
$501,249
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group