The Flats Homes

/42
$2,700,000 Sold Aug 18, 2025
- 3,708 Sq Ft
- $728/SF
- 2 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1929
34 Rangeley Rd, Winchester, MA 01890

Welcome to this truly distinctive home nestled on a lush landscaped lot in historic & highly sought after Rangeley Estates neighborhood. Just moments from downtown Winchester, this hidden gem offers a unique blend of privacy and convenience! This stunning home boasts 5 bedrooms & 4 full baths, seamlessly blending original charm with modern amenities. Step inside to discover sun-filled rooms and a

Kim Covino Compass

34 Rangeley Rd, Winchester, MA 01890

/42
Est $2,336,240 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 4,031 Sq Ft
3 Fletcher St, Winchester, MA 01890

3 Fletcher St, Winchester, MA 01890

/42
$1,285,000 Pending
- 4 Beds
- 1.5 Baths
- 2,696 Sq Ft
104 Church St, Winchester, MA 01890

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

Kim Covino Compass

104 Church St, Winchester, MA 01890
/42
$3,745,000 Sold Aug 08, 2025
- 7,587 Sq Ft
- $494/SF
- 44 Days On Market
- 7 Beds
- 8 Baths
- Built 2010
25 Wedgemere Ave, Winchester, MA 01890

Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

Prestige Homes Realty Team Prestige Homes Real Estate, LLC

25 Wedgemere Ave, Winchester, MA 01890

/40
Est $2,804,083 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,347 Sq Ft
10 Cabot St, Winchester, MA 01890

10 Cabot St, Winchester, MA 01890

/42
$1,975,000 Pending
- 6 Beds
- 3.5 Baths
- 3,521 Sq Ft
19 Glengarry Rd, Winchester, MA 01890

A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic

Kim Covino Compass

19 Glengarry Rd, Winchester, MA 01890
/39
$1,400,000 Sold Jul 14, 2025
- 2,282 Sq Ft
- $613/SF
- 38 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
20 Fletcher St Unit 20, Winchester, MA 01890

Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

Kim Covino Compass

20 Fletcher St Unit 20, Winchester, MA 01890

/41
Est $2,996,065 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,263 Sq Ft
30 Wedgemere Ave, Winchester, MA 01890

30 Wedgemere Ave, Winchester, MA 01890

/42
$3,750,000 Pending
- 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
/42
$2,500,000 Sold Jul 14, 2025
- 3,719 Sq Ft
- $672/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1952
17 Harrison St, Winchester, MA 01890

Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

17 Harrison St, Winchester, MA 01890

/4
Est $3,690,734 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
40 Foxcroft Rd, Winchester, MA 01890

40 Foxcroft Rd, Winchester, MA 01890

/28
$1,260,000 Sold Jun 30, 2025
- 2,705 Sq Ft
- $466/SF
- 41 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1885
261 Cambridge St Unit 261 G, Winchester, MA 01890

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

261 Cambridge St Unit 261 G, Winchester, MA 01890

/33
Est $1,749,318 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,938 Sq Ft
133 Cambridge St, Winchester, MA 01890

133 Cambridge St, Winchester, MA 01890

/35
$1,100,000 Sold Jun 27, 2025
- 3,157 Sq Ft
- $348/SF
- 20 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1866
63 Church St, Winchester, MA 01890

Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

Nancy McLaughlin Redfin Corp.

63 Church St, Winchester, MA 01890

/41
Est $2,351,693 Not Listed For Sale
- 5 Beds
- 5 Baths
- 4,182 Sq Ft
24 Calumet Rd, Winchester, MA 01890

24 Calumet Rd, Winchester, MA 01890

/22
$4,200,000 Sold Jun 26, 2025
- 5,208 Sq Ft
- $806/SF
- 4 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2025
3 Foxcroft Rd, Winchester, MA 01890

Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebuilt, expanded & tastefully renovated home is one of a kind, offering a perfect blend of elegance & modern sophistication for a lifestyle of luxury & comfort. Step inside to discover a beautifully designed interior that exudes charm & style

Kim Covino Compass

3 Foxcroft Rd, Winchester, MA 01890

/31
Not Listed For Sale
- 7 Beds
- 5.5 Baths
- 4,636 Sq Ft
127 Church St, Winchester, MA 01890

127 Church St, Winchester, MA 01890

/42
$2,950,000 Sold Jun 23, 2025
- 4,279 Sq Ft
- $689/SF
- 23 Days On Market
- 5 Beds
- 5 Baths
- Built 1914
51 Wedgemere Ave, Winchester, MA 01890

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy

Kim Covino Compass

51 Wedgemere Ave, Winchester, MA 01890

/42
Est $1,502,130 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,863 Sq Ft
62 Bacon St, Winchester, MA 01890

62 Bacon St, Winchester, MA 01890

/42
$2,350,000 Sold Jun 16, 2025
- 4,212 Sq Ft
- $558/SF
- 15 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1880
19 Yale St, Winchester, MA 01890

Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

Nancy Pallotta Gibson Sotheby's International Realty

19 Yale St, Winchester, MA 01890

/35
Est $1,399,609 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,430 Sq Ft
97 Cambridge St, Winchester, MA 01890

97 Cambridge St, Winchester, MA 01890

/40
$3,025,000 Sold Jun 13, 2025
- 5,198 Sq Ft
- $582/SF
- 50 Days On Market
- 6 Beds
- 5 Baths
- Built 1910
21 Sheffield W, Winchester, MA 01890

Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

Kim Covino Compass

21 Sheffield W, Winchester, MA 01890

/37
Est $1,856,871 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,436 Sq Ft
111 Cambridge St, Winchester, MA 01890

111 Cambridge St, Winchester, MA 01890

/38
$2,600,000 Sold May 19, 2025
- 4,060 Sq Ft
- $640/SF
- 88 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1912
3 Lagrange St, Winchester, MA 01890

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury.

Mark Donnellan Gibson Sotheby's International Realty

3 Lagrange St, Winchester, MA 01890

/42
Est $2,211,329 Not Listed For Sale
- 6 Beds
- 2.5 Baths
- 3,892 Sq Ft
30 Glen Rd, Winchester, MA 01890

30 Glen Rd, Winchester, MA 01890

/39
$4,650,000 Sold May 01, 2025
- 7,779 Sq Ft
- $598/SF
- 5 Days On Market
- 5 Beds
- 7 Baths
- Built 1915
19 Rangeley Rd, Winchester, MA 01890

A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to bring this cherished home back to life with a renovation that bestowed the best of everything. On Rangeley Road, gentle rolling lawns fold softly into a private, winding road. Gorgeous architecture graces every lot and ancient oaks stand sentry. Located just steps to the town

Nancy Pallotta Gibson Sotheby's International Realty

19 Rangeley Rd, Winchester, MA 01890

/42
Est $2,582,288 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,755 Sq Ft
3 Sheffield Rd, Winchester, MA 01890

3 Sheffield Rd, Winchester, MA 01890

/42
$2,420,000 Sold Apr 25, 2025
- 4,173 Sq Ft
- $580/SF
- 8 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1914
48 Wedgemere Ave, Winchester, MA 01890

This elegant 1914 Revival home combines timeless charm w/ exceptional architectural details. Located on a highly sought-after, picturesque street in "The Flats," this 5-bedroom, 4 1/2 half-bath residence offers spacious living throughout. The main floor boasts a formal living room w/ built-in bookcases & fireplace, a grand dining room, & a kitchen w/ two impressive butler’s pantries. Inviting

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

48 Wedgemere Ave, Winchester, MA 01890

/31
Est $2,053,139 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,529 Sq Ft
11 Stratford Rd, Winchester, MA 01890

11 Stratford Rd, Winchester, MA 01890

/42
$2,500,000 Sold Apr 18, 2025
- 3,851 Sq Ft
- $649/SF
- 4 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1936
7 Rangeley Rd, Winchester, MA 01890

**OFFER ACCEPTED/ OH CANCELED* Delightful home in Rangeley Estates, just outside Winchester Center! Featuring 5 bedrooms & 4.5 baths; 2 primary bedroom options w/ en-suite baths. A unique layout w/ a California vibe w/open airy spaces perfect for modern day living & just steps from the vibrant downtown. Enjoy easy access to Train, schools, shops, coffee, dining & more, while being tucked away in

Kim Covino Compass

7 Rangeley Rd, Winchester, MA 01890

/40
Est $2,642,459 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,938 Sq Ft
19 Everett Ave, Winchester, MA 01890

19 Everett Ave, Winchester, MA 01890

/41
$2,350,000 Sold Apr 15, 2025
- 4,273 Sq Ft
- $550/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1910
5 Pine St, Winchester, MA 01890

This recently renovated Victorian blends historic charm with modern luxury in a prime in-town location-minutes to the shops, Common, train and Wedge Pond. Step into the central hall showcasing elegant woodwork, high ceilings, and gleaming floors. The new kitchen features high-end appliances, a butler’s pantry, and dining banquette. Entertain in the sun-drenched dining room with a marble fireplace

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Pine St, Winchester, MA 01890

/42
Est $3,599,014 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 6,600 Sq Ft
33 Everett Ave, Winchester, MA 01890

33 Everett Ave, Winchester, MA 01890

/39
$2,224,000 Sold Apr 11, 2025
- 3,487 Sq Ft
- $638/SF
- 8 Days On Market
- 6 Beds
- 2.5 Baths
- Built 1910
5 Woodside Rd, Winchester, MA 01890

Introducing a captivating waterside home on a gorgeous 34,000 sf lot, located in a top location w/ expansive frontage on Little Winter Pond. This 6-bedroom, 2.5-bathroom home offers unparalleled access to the picturesque pond for activities such as ice skating, fishing, kayaking, & more. The home’s interior is highlighted by high ceilings, hardwood floors & an original fireplace for cozy winter

Kim Covino Compass

5 Woodside Rd, Winchester, MA 01890

/42
Est $4,574,206 Not Listed For Sale
- 7 Beds
- 6.5 Baths
- 9,075 Sq Ft
48 Everett Ave, Winchester, MA 01890

48 Everett Ave, Winchester, MA 01890

/42
$3,665,000 Sold Mar 27, 2025
- 5,768 Sq Ft
- $635/SF
- 1 Day On Market
- 5 Beds
- 4.5 Baths
- Built 1895
6 Lakeview Rd, Winchester, MA 01890

Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company committed to blending historical integrity with modern amenities, paying meticulous attention to every

Kim Covino Compass

6 Lakeview Rd, Winchester, MA 01890

/42
Est $5,285,583 Not Listed For Sale
- 7 Beds
- 6 Baths
- 9,835 Sq Ft
32 Everett Ave, Winchester, MA 01890

32 Everett Ave, Winchester, MA 01890

/42
$2,350,000 Sold Mar 24, 2025
- 3,059 Sq Ft
- $768/SF
- 6 Days On Market
- 5 Beds
- 2 Baths
- Built 1940
17 Dix St, Winchester, MA 01890

Prime Waterfront home in downtown Winchester!! Take advantage of this unique opportunity to customize, renovate, expand or rebuild your dream home on this heavenly 1/2 acre lot with gorgeous grounds and expansive frontage on Wedge Pond. The current home was custom built and enjoyed by one family who made unforgettable memories here including skating, swimming, canoeing & sledding right in their

Kim Covino Compass

17 Dix St, Winchester, MA 01890

/24
Est $743,753 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,432 Sq Ft
10 Wyman Ct, Winchester, MA 01890

10 Wyman Ct, Winchester, MA 01890

/42
$3,250,000 Sold Mar 18, 2025
- 4,714 Sq Ft
- $689/SF
- 9 Days On Market
- 6 Beds
- 6 Baths
- Built 1909
23 Everett Ave, Winchester, MA 01890

Talk about curb appeal! This fabulous Colonial home beckons with an amazing front porch overlooking an expansive front yard, proudly perched on a quiet corner in one of the most coveted neighborhoods in town. Well-tended gardens and plants mesh with giant overhanging oak trees making your heart sing. Inside, delight in the quarter-sawn oak walls and floors, huge sunny family room and a dining

Nancy Pallotta Gibson Sotheby's International Realty

23 Everett Ave, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18

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