Winchester, MA Homes

/42
Est $1,396,191 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,381 Sq Ft
24 Brookside Ave, Winchester, MA 01890

24 Brookside Ave, Winchester, MA 01890

/36
$1,470,000 Sold Jun 04, 2024
- 4,190 Sq Ft
- $351/SF
- 48 Days On Market
- 4 Beds
- 3 Baths
- Built 1970
43 Mayflower Rd, Winchester, MA 01890

Sunny, bright and spacious! This residence is tailor-made for hosting gatherings. The open concept living and dining room is adjacent to the chef’s kitchen, complete with high end appliances, ample counter space and 2 skylights. But the real gem is the 4 season room just off the kitchen offering a tranquil retreat to enjoy your morning coffee while enjoying the beauty of the changing seasons.

Annie Youssoufian Boston Brownstones Realty PLLC

43 Mayflower Rd, Winchester, MA 01890

/26
Est $1,184,531 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,545 Sq Ft
18 Brookside Ave, Winchester, MA 01890

18 Brookside Ave, Winchester, MA 01890

/41
$1,150,000 Sold Jun 03, 2024
- 1,696 Sq Ft
- $678/SF
- 7 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1958
28 Garfield Ave, Winchester, MA 01890

This spacious home with thoughtful design details was carefully maintained through the years by original owner/builder. On first floor, be welcomed to a large living room with fireplace (plenty of space for multiple seating zones/uses), the dining room has custom built in storage that can be removed, half bath, enclosed porch and beautifully designed kitchen with eating area and bright sunny

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

28 Garfield Ave, Winchester, MA 01890

/29
Est $1,003,671 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,380 Sq Ft
88 Forest St, Winchester, MA 01890

88 Forest St, Winchester, MA 01890

/42
$2,650,000 Sold Jun 03, 2024
- 5,678 Sq Ft
- $467/SF
- 12 Days On Market
- 5 Beds
- 6 Baths
- Built 1994
19 Socrates Way, Winchester, MA 01890

LOCATION -LOCATION - LOCATION - the most important advice and fact in Real Estate... CUSTOM BUILT HOME - PRISTINE CONDITION - 7 MILES to BOSTON - HALF ACRE - PERFECT FLAT LOT - RARE FIND in WINCHESTER - PRISTINE CONDITION - SPACE for YOUR EVERY DESIRE. Having 14 Rooms - 5+ Bedrooms, 4 Full Bathrooms and 2 Half Bathrooms - 3 flrs of finished living space with a magnificent Grand Two-Story Entrance

Lucille Murray Advisors Living - Winchester

19 Socrates Way, Winchester, MA 01890

/42
Est $1,410,362 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,347 Sq Ft
15 Garfield Ave, Winchester, MA 01890

15 Garfield Ave, Winchester, MA 01890

/35
$1,450,000 Sold May 31, 2024
- 2,132 Sq Ft
- $680/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1930
29 Kenwin Rd, Winchester, MA 01890

Charming 1930's Cape with arched doorways, built-ins, period details and several recent updates. Located in the desirable "Highlands" section of Winchester and within walking distance of the Muraco Elementary School, Leonard Field, the Fells Reservation and Winchester Hospital . Enjoy spacious rooms with several improvements including a striking remodeled eat in kitchen with white cabinets,

Judith Moore Barrett Sotheby's International Realty

29 Kenwin Rd, Winchester, MA 01890

/36
Est $938,853 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,288 Sq Ft
27 Garfield Ave, Winchester, MA 01890

27 Garfield Ave, Winchester, MA 01890

/38
$1,825,000 Sold May 31, 2024
- 5,484 Sq Ft
- $333/SF
- 4 Days On Market
- 5 Beds
- 4 Baths
- Built 1984
94 Lawson Rd, Winchester, MA 01890

Incredibly deceptive from the front, this ideally located home is great at keeping a secret about what's behind the front door...Space, space & more space. W/well over 5000sf over 3 fls, this home sits in a neighborhood that is often described as the "BEST STREET IN DOWNTOWN WINCHESER." It's exactly where you want to be. Often sought, but rarely found is a home in this MOST DESIRED NEIGHBORHOOD.

Rick Nazzaro Colonial Manor Realty

94 Lawson Rd, Winchester, MA 01890

/41
Est $1,260,046 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,302 Sq Ft
39 Forest St, Winchester, MA 01890

39 Forest St, Winchester, MA 01890

/27
$1,670,000 Sold May 30, 2024
- 2,549 Sq Ft
- $655/SF
- 59 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2019
5 Gershon Way Unit 5, Winchester, MA 01890

Welcome to Winchester's premier 55+ community, a luxurious enclave nestled on the coveted west side. This unit is a perfect blend of modernity and comfort, all while enjoying the utmost privacy in this premiere location within the development. Step into a world of sophistication, where 10' ceilings, rich hardwood floors, & an abundance of natural light create an inviting ambiance. The open

Monte Marrocco Coldwell Banker Realty - Lexington

5 Gershon Way Unit 5, Winchester, MA 01890

/41
Est $1,174,797 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,281 Sq Ft
502 Washington St, Winchester, MA 01890

502 Washington St, Winchester, MA 01890

/42
$1,910,000 Sold May 29, 2024
- 2,853 Sq Ft
- $669/SF
- 7 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1992
40 Wainwright Rd, Winchester, MA 01890

Discover the allure of this beautiful home nestled on an oversized 21,000sf private lot abutting conservation! This exceptional and meticulously maintained home boasts a flawless layout designed for comfort and functionality with large flowing rooms perfect for hosting parties & family gatherings. The stylish eat in kitchen offers granite countertops, espresso cabinetry and high end appliances

Kim Covino Compass

40 Wainwright Rd, Winchester, MA 01890

/35
Est $957,950 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,726 Sq Ft
21 Holton St, Winchester, MA 01890

21 Holton St, Winchester, MA 01890

/42
$2,285,000 Sold May 29, 2024
- 3,755 Sq Ft
- $609/SF
- 10 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1907
3 Sheffield Rd, Winchester, MA 01890

Amazing 1907 six bedroom three and one half bath Colonial Revival located in one of Winchesters finest neighborhoods.This home is a tribute to yesteryear with its custom detail and design, magnificent woodwork, high coffered ceilings ,beautiful hardwood floors and four fireplaces.Imagine entertaining in the lovely front to back living room or enjoying the holidays by the fire in this most

Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

3 Sheffield Rd, Winchester, MA 01890

/42
Est $2,160,947 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,350 Sq Ft
7 Nathaniel Rd, Winchester, MA 01890

7 Nathaniel Rd, Winchester, MA 01890

/41
$2,349,000 Sold May 29, 2024
- 4,583 Sq Ft
- $513/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2007
148 Highland Ave, Winchester, MA 01890

Modern luxuries & exquisite finishes! This impeccably renovated 5 BR 3 ½ BA home showcasing infinite high-end details is located just outside the Middlesex Fells. The centerpiece is the expansive chef’s kitchen featuring custom cabinetry, marble countertops/island, 6-burner Wolf cooktop, double ovens, Sub-Zero fridge, beverage center & dining area. The open floor plan seamlessly connects the

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

148 Highland Ave, Winchester, MA 01890

/38
Est $1,346,779 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,799 Sq Ft
39 Nathaniel Rd, Winchester, MA 01890

39 Nathaniel Rd, Winchester, MA 01890

/32
$2,080,000 Sold May 24, 2024
- 4,055 Sq Ft
- $513/SF
- 2 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2023
6 Loring Ct, Winchester, MA 01890

Must see this gorgeous 4 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end appliances and walk in pantry. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/

Kim Covino Compass

6 Loring Ct, Winchester, MA 01890

/38
Est $1,229,447 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,681 Sq Ft
32 Nathaniel Rd, Winchester, MA 01890

32 Nathaniel Rd, Winchester, MA 01890

/31
$932,700 Sold May 24, 2024
- 2,170 Sq Ft
- $430/SF
- 4 Days On Market
- 6 Beds
- 2.5 Baths
- Built 1890
47 Clark St Unit 49, Winchester, MA 01890

Lots of possibility in this rare side-by-side two family conveniently located near downtown Winchester. Great potential for those looking for an owner occupant opportunity, investors and contractors. Each unit has separate utilities, basement and driveway.

Kristi Connors - Taylor Coldwell Banker Realty - Lexington

47 Clark St Unit 49, Winchester, MA 01890

/42
Est $2,156,318 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,634 Sq Ft
15 Tufts Rd, Winchester, MA 01890

15 Tufts Rd, Winchester, MA 01890

/41
$2,945,000 Sold May 24, 2024
- 4,274 Sq Ft
- $689/SF
- 9 Days On Market
- 5 Beds
- 5 Baths
- Built 1934
7 Wolcott Rd, Winchester, MA 01890

Welcome to 7 Wolcott Rd, a truly iconic French country colonial, carefully designed to embrace its incredible location at the edge of the Fells nature preserve. Every detail has been thoughtfully engineered to respect and reflect the beautiful natural setting. This home takes its inspiration from the original 1934 stone cottage. With the completion of the addition in 2015 it is now a gorgeous 10

Naomi Delairre Barrett Sotheby's International Realty

7 Wolcott Rd, Winchester, MA 01890

/24
Est $1,196,482 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,139 Sq Ft
32 Tufts Rd, Winchester, MA 01890

32 Tufts Rd, Winchester, MA 01890

/34
$1,542,500 Sold May 24, 2024
- 2,128 Sq Ft
- $725/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 1860
23 Hancock St, Winchester, MA 01890

Incredibly charming 3 bedroom 2 bath home w/ stunning rear addition nestled on a fabulous oversized lot in a prime location! As you enter you’ll be greeted by a warm & inviting floor plan showcasing historic charm & modern day style. The rear addition boasts a stunning family room w/ stone gas fireplace, vaulted ceiling & wall of windows overlooking spectacular yard w/ large patio, beautiful

Kim Covino Compass

23 Hancock St, Winchester, MA 01890

/34
Est $1,050,843 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,918 Sq Ft
5 Bates Rd, Winchester, MA 01890

5 Bates Rd, Winchester, MA 01890

/41
$2,672,000 Sold May 23, 2024
- 5,267 Sq Ft
- $507/SF
- 5 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1999
4 Davey Ln, Winchester, MA 01890

Step into refined living with this gorgeous 5-bedroom, 4.5-bathroom colonial home tucked away on a quiet cul-de-sac. You'll be greeted by a spacious layout with a chef's kitchen featuring a top-of-the-line 48" Sub Zero refrigerator/freezer, a gas range topped with a stylish hood, and a cozy breakfast bar. The dining area, boasting cathedral ceilings and a double-sided fireplace, seamlessly flows

Gayle Winters Compass

4 Davey Ln, Winchester, MA 01890

/35
Est $1,274,675 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,565 Sq Ft
63 Irving St, Winchester, MA 01890

63 Irving St, Winchester, MA 01890

/33
$1,825,000 Sold May 23, 2024
- 4,603 Sq Ft
- $396/SF
- 2 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1960
8 Olde Lyme Rd, Winchester, MA 01890

Get ready to live your dream life! This house isn't just a home; it's a lifestyle upgrade! Step inside and prepare to be amazed by the huge family room, perfect for hosting Netflix marathons and epic game nights. The open kitchen and dining room are ready for your gourmet creations or takeout feasts – no judgment here. The real star of the show? A huge 3-season porch; highly coveted but rarely

Nancy Pallotta Advisors Living - Winchester

8 Olde Lyme Rd, Winchester, MA 01890

/35
Est $877,951 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,252 Sq Ft
42 Irving St, Winchester, MA 01890

42 Irving St, Winchester, MA 01890

/42
$2,750,000 Sold May 21, 2024
- 5,208 Sq Ft
- $528/SF
- 53 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2023
11 Brooks St, Winchester, MA 01890

A private estate nestled in one of Winchester's hidden gem locales! The first floor open floor plan showcases a kitchen replete with luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive living room with gas fireplace & custom built-ins flows into a sunroom and outdoor patio surrounded by a canopy of trees. Coffered

Michaela Mahtani Leading Edge Real Estate

11 Brooks St, Winchester, MA 01890

/34
Est $1,089,324 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,477 Sq Ft
30 Irving St Unit 32, Winchester, MA 01890

30 Irving St Unit 32, Winchester, MA 01890

/41
$2,700,000 Sold May 21, 2024
- 6,864 Sq Ft
- $393/SF
- 34 Days On Market
- 7 Beds
- 6.5 Baths
- Built 1900
319 Main St, Winchester, MA 01890

OPEN HOUSE 03/09 SATURDAY 12:30-2! Don't miss this extraordinary masterpiece of architectural beauty & refined elegance showcasing a blend of old world craftsmanship & modern day luxuries. The grand 1st floor w/ 10' ceilings flows beautifully from the stunning foyer into the fabulous dining room, living room w/ ornate fplc, 2 family rooms, breakfast room & sunroom, a floor plan ideal for

Kim Covino Compass

319 Main St, Winchester, MA 01890

/34
Est $1,217,345 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,880 Sq Ft
74 Chester St, Winchester, MA 01890

74 Chester St, Winchester, MA 01890

/2
$850,000 Sold May 17, 2024
- 1,668 Sq Ft
- $510/SF
- 3 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1985
54 Edward Dr Unit 54, Winchester, MA 01890

Located in the desirable Pepper Hill Estates, this fully renovated townhouse with open floor plan, beautiful hardwood floor throughout. Filled with sun light, bright and airy, updated white kitchen with stainless steel appliances, marble back splash, and large bay window. Dining room right off the kitchen and opens to the oversized living room with wood burning fireplace. Large bedroom and a half

Shell Yu JT Fleming & Company

54 Edward Dr Unit 54, Winchester, MA 01890

/39
Est $1,071,166 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
29 Harvard St, Winchester, MA 01890

29 Harvard St, Winchester, MA 01890

/42
$2,625,000 Sold May 17, 2024
- 5,315 Sq Ft
- $494/SF
- 0 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1930
6 Agawam Rd, Winchester, MA 01890

Welcome to this elegant single family home located at 6 Agawam Rd, Winchester, MA. This classic and private residence offers a spacious 5,315 square feet of living space. Featuring 5 bedrooms, 3.5 bathrooms and 3 levels, providing ample space for comfortable living and entertaining. Upon entering, you are greeted by timeless architecture, built-ins, refinished hardwood floor and attention to

Leigh Ventura Compass

6 Agawam Rd, Winchester, MA 01890

/33
Est $962,695 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,770 Sq Ft
316 Washington St, Winchester, MA 01890

316 Washington St, Winchester, MA 01890

/17
$1,100,000 Sold May 16, 2024
- 2,016 Sq Ft
- $546/SF
- 3 Days On Market
- 5 Beds
- 3 Baths
- Built 1960
269 Cross St Unit 271, Winchester, MA 01890

Welcome to The Residences at Winchester, where this unique multi-family property awaits. Boasting gleaming hardwood floors and updated kitchens and baths, each unit exudes modern elegance and comfort. Situated in a highly desirable location close to major highways, convenience is at your doorstep. Good investment opportunity with long term tenants. Or you can convert to owner occupied. Unit 1 is

Hongmei Wang HMW Real Estate, LLC

269 Cross St Unit 271, Winchester, MA 01890

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Massachusetts Winchester

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