Winchester, MA Homes

/34
$1,071,000 Sold Dec 05, 2024
- 2,186 Sq Ft
- $490/SF
- 8 Days On Market
- 5 Beds
- 3 Baths
- Built 1880
63-65 Harvard St, Winchester, MA 01890

Discover this rare multi-family gem in a highly desirable Winchester neighborhood, offering endless possibilities for savvy investors, owner-occupants, or multi-generational living. Situated on a large, flat, private lot with a detached two-car garage and ample off-street parking, this home perfectly balances charm, function, and convenience. The first-floor unit includes two bedrooms, a bright

Nancy Pallotta Advisors Living - Winchester

63-65 Harvard St, Winchester, MA 01890

/42
Est $2,466,480 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,775 Sq Ft
76 Yale St, Winchester, MA 01890

76 Yale St, Winchester, MA 01890

/34
$2,499,000 Pending
- 4 Beds
- 3.5 Baths
- 5,218 Sq Ft
31 Lawson Rd, Winchester, MA 01890

Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today’s lifestyle. Located in one of Winchester’s most desirable neighborhoods, you’ll enjoy easy access to top-rated schools, the commuter rail, and downtown. This home showcases deep moldings along w/ a stunning kitchen that naturally flows into the living/dining area & family room,

Monte Marrocco Coldwell Banker Realty - Lexington

31 Lawson Rd, Winchester, MA 01890
/42
$2,900,000 Sold Dec 03, 2024
- 4,215 Sq Ft
- $688/SF
- 32 Days On Market
- 4 Beds
- 5 Baths
- Built 1917
27 Cabot St, Winchester, MA 01890

Meticulously renovated home in desirable Winchester Flats! Set on a tranquil corner lot surrounded by mature trees, less than a mile from schools, Winchester Center, and commuter rail, this exquisite four-level Tudor offers the perfect blend of modern elegance and classic charm. The main level showcases 2 inviting family rooms adorned with fireplace and integrated sound system, gourmet kitchen

The McLaren D'Agostino Team Compass

27 Cabot St, Winchester, MA 01890

/36
Est $3,669,782 Not Listed For Sale
- 6 Beds
- 6 Baths
- 6,073 Sq Ft
25 Dartmouth St, Winchester, MA 01890

25 Dartmouth St, Winchester, MA 01890

/41
$1,499,000 Pending
- 4 Beds
- 3.5 Baths
- 4,214 Sq Ft
7 Wainwright Rd Unit 117, Winchester, MA 01890

Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 117, Winchester, MA 01890
/37
$2,899,999 Sold Dec 03, 2024
- 7,242 Sq Ft
- $400/SF
- 8 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2010
50 Lorena Rd, Winchester, MA 01890

Stunning cedar shingle Colonial home nestled in sought-after East Hill. As you step inside, you are greeted by an elegant foyer leading to a chef's kitchen with center island, pantry, granite counters, SS appliances and a sun-filled dining area.The kitchen seamlessly flows to a stone deck, perfect for grilling and alfresco dining. Large family room wrapped with windows featuring a stone

Leigh Ventura Compass

50 Lorena Rd, Winchester, MA 01890

/32
Est $1,878,458 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,350 Sq Ft
57 Wildwood St, Winchester, MA 01890

57 Wildwood St, Winchester, MA 01890

/42
$3,199,000 Pending
- 5 Beds
- 5 Baths
- 4,279 Sq Ft
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
/38
$3,800,000 Sold Dec 03, 2024
- 5,500 Sq Ft
- $691/SF
- 47 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1951
25 Ledgewood Rd, Winchester, MA 01890

Nestled on 1.1 acres in Winchester, this fully custom renovated home is truly a hidden gem. The property is well secluded from the main road, offering a tranquil retreat. Transformed in 2024, this home features 5 spacious beds, 4.5 baths and custom spaces throughout. The grand kitchen, with white oak accents, is a culinary centerpiece. The light-filled family room has expansive windows and a

Mark Donnellan Advisors Living - Winchester

25 Ledgewood Rd, Winchester, MA 01890

/42
Est $1,997,801 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,003 Sq Ft
12 Woodside Rd, Winchester, MA 01890

12 Woodside Rd, Winchester, MA 01890

/19
$3,599,000 Pending
- 6 Beds
- 5 Baths
- 5,500 Sq Ft
2 Chestnut St, Winchester, MA 01890

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering

Mark Donnellan Advisors Living - Winchester

2 Chestnut St, Winchester, MA 01890
/19
$377,000 Sold Dec 02, 2024
- 634 Sq Ft
- $595/SF
- 5 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
200 Swanton St Unit T26, Winchester, MA 01890

Ideal for first-time homeowners, down-sizers, or investors. Desirable private/direct-entry terrace level 1BD, 1BA condo overlooking scenic duck ponds and lush landscape at The Parkview, Winchester’s iconic Midcentury Modern building. With 634 Sq. Ft. this unit offers ample space for dining, living & bedroom area with a large walk in closet! Association amenities include a pool for hot summer

Gretchen Chingris Metropolitan Boston Real Estate, LLC

200 Swanton St Unit T26, Winchester, MA 01890

/42
Est $1,514,775 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,562 Sq Ft
32 Woodside Rd, Winchester, MA 01890

32 Woodside Rd, Winchester, MA 01890

/9
$2,899,000 Pending
- 6 Beds
- 7.5 Baths
- 5,658 Sq Ft
5 Clearwater Rd, Winchester, MA 01890

Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxurious canvas for your vision, offering 6 bedrooms, 7.5 baths, and 5,658 sq. ft. of meticulously planned living space. The spectacular floor plan seamlessly combines modern sophistication with timeless elegance, offering the perfect

Monte Marrocco Coldwell Banker Realty - Lexington

5 Clearwater Rd, Winchester, MA 01890
/42
$2,375,000 Sold Dec 02, 2024
- 5,279 Sq Ft
- $450/SF
- 7 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2014
7 Bellevue Ave, Winchester, MA 01890

Exceptionally designed & meticulously maintained 2015 Contemporary Colonial. Elegant farmers porch welcomes you into a magnificent layout w/ exquisite mouldings, wainscotting, oak hardwoods, custom fixtures/millwork, & plantation shutters. Spectacular, open-concept main level boasts dual island, granite/stainless chef’s kitchen w/ 2 ovens, butler’s pantry, built-in buffet, walk-in pantry, &

Cam Chesley Keller Williams Realty Boston-Metro | Back Bay

7 Bellevue Ave, Winchester, MA 01890

/32
Est $1,357,801 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,894 Sq Ft
114 Pond St, Winchester, MA 01890

114 Pond St, Winchester, MA 01890

/7
$3,450,000 Pending
- 5 Beds
- 4.5 Baths
- 4,800 Sq Ft
58 Wedgemere Ave, Winchester, MA 01890

Experience the timeless charm of this stunning English Tudor in Winchester’s coveted Flats neighborhood. Set on an oversized lot with mature landscaping, this home is undergoing a full renovation and expansion by Mark Stephen Development, blending classic elegance with modern luxury. The reimagined design features two fireplaces, an expansive family room, living room, dining room, first- and

Mark Donnellan Advisors Living - Winchester

58 Wedgemere Ave, Winchester, MA 01890
/34
$1,580,000 Sold Nov 29, 2024
- 2,650 Sq Ft
- $596/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1900
78 Middlesex St, Winchester, MA 01890

Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud room & 1/2 bath. Upstairs has a primary bedroom suite, bath with 2 separate vanities, walk-in custom

Marjie and Phil Advisors Living - Arlington

78 Middlesex St, Winchester, MA 01890

/40
Est $1,264,149 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,919 Sq Ft
94 Pond St, Winchester, MA 01890

94 Pond St, Winchester, MA 01890

/22
$4,200,000 Pending
- 6 Beds
- 5.5 Baths
- 5,208 Sq Ft
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
/38
$1,300,000 Sold Nov 22, 2024
- 3,122 Sq Ft
- $416/SF
- 111 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
14 Pine Grove Park Unit 14, Winchester, MA 01890

Welcome to this newly constructed luxurious 4-bedroom, 3.5-bathroom townhome spanning four levels of exquisite living space! Step through the charming covered porch into the striking open floor plan. The elegant living room boasts expansive windows, custom fireplace wall and hardwood floors. The showstopper kitchen dazzles with gorgeous white cabinetry accented by gold details, quartz countertops

Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

14 Pine Grove Park Unit 14, Winchester, MA 01890

/42
Est $3,341,227 Not Listed For Sale
- 5 Beds
- 5 Baths
- 4,550 Sq Ft
47 Wedgemere Ave, Winchester, MA 01890

47 Wedgemere Ave, Winchester, MA 01890

/40
$1,600,000 Pending
- 5 Beds
- 2 Baths
- 2,331 Sq Ft
149 Horn Pond Brook Rd, Winchester, MA 01890

Picture perfect cape style home across from the Lynch Elementary School. This beautiful home on a corner lot checks all the boxes with 4/5 bedrooms on 2 floors and 2 full baths. Extra bonus space in lower level for home office or gym. Huge, beautiful yard that is perfect for outdoor recreation. Pretty eat in kitchen has direct entry to deck. This custom built home has been lovingly maintained

Nancy McLaughlin Redfin Corp.

149 Horn Pond Brook Rd, Winchester, MA 01890
/30
$900,000 Sold Nov 21, 2024
- 1,857 Sq Ft
- $485/SF
- 6 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1985
62 Edward Dr, Winchester, MA 01890

Welcome to 62 Edward Drive in the sought-after Pepper Hill Estates. This spacious townhouse-style condo features two bedrooms and a versatile bonus room on the lower level, perfect for a home office, guest space, or playroom. The well-maintained home boasts an open living and dining area filled with natural light and a beautiful fireplace. The updated kitchen includes granite countertops, newer

Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

62 Edward Dr, Winchester, MA 01890

/37
Est $2,216,760 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,696 Sq Ft
21 Foxcroft Rd, Winchester, MA 01890

21 Foxcroft Rd, Winchester, MA 01890

/35
$1,060,000 Pending
- 5 Beds
- 2.5 Baths
- 2,849 Sq Ft
62 Richardson St, Winchester, MA 01890

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

Frank Ventresca Strategy Street

62 Richardson St, Winchester, MA 01890
/30
$1,050,000 Sold Nov 21, 2024
- 2,136 Sq Ft
- $492/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1926
359-361 Washington St, Winchester, MA 01890

Welcome to this well-maintained two-unit multi-family home, perfect for investors or owner-occupants seeking a spacious living arrangement with rental income potential. Each unit boasts two well apportioned bedrooms and dedicated in-home office areas, ideal for today’s work-from-home lifestyle. Enjoy the convenience of off-street parking along with two garage bays, ensuring easy access for you

Anne Spry Barrett Sotheby's International Realty

359-361 Washington St, Winchester, MA 01890

/39
Est $2,106,642 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 4,605 Sq Ft
61 Oxford St, Winchester, MA 01890

61 Oxford St, Winchester, MA 01890

/2
$999,999 Pending
- 2 Beds
- 1 Bath
- 1,666 Sq Ft
26 North Gateway, Winchester, MA 01890

LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of

Robert Dell Homes Unlimited

26 North Gateway, Winchester, MA 01890
/42
$2,200,000 Sold Nov 21, 2024
- 3,969 Sq Ft
- $554/SF
- 6 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1865
7 Herrick St, Winchester, MA 01890

Step into a world of timeless elegance in this beautifully preserved home, where classic architectural details seamlessly blend with modern comfort. The inviting front porch welcomes you. Inside, high ceilings complement a living room w/beamed ceilings & custom built-ins, a gracious dining room, & a light-filled, eat-in kitchen. The cozy family room offers a charming window seat. A quaint stone

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

7 Herrick St, Winchester, MA 01890

/42
Est $2,683,291 Not Listed For Sale
- 7 Beds
- 3.5 Baths
- 5,616 Sq Ft
49 Oxford St, Winchester, MA 01890

49 Oxford St, Winchester, MA 01890

/2
$674,900
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
20 Arthur St, Winchester, MA 01890

Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show.

Dan O'Connell LAER Realty Partners

20 Arthur St, Winchester, MA 01890
/42
$2,250,000 Sold Nov 20, 2024
- 4,026 Sq Ft
- $559/SF
- 10 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2006
18 Town Way, Winchester, MA 01890

Stunning 2006 Colonial, meticulously maintained & decorator-perfect. A grand entry with high ceilings and elegant archways welcomes you into this sun-filled home. The charming living & dining rooms showcase custom details throughout. The gourmet granite kitchen features an oversized island with seating for four, dining area & high-end amenities. A mudroom with ample storage is conveniently

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

18 Town Way, Winchester, MA 01890

/24
Est $2,163,359 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,516 Sq Ft
38 Cabot St, Winchester, MA 01890

38 Cabot St, Winchester, MA 01890

/38
$1,670,000 Sold Nov 20, 2024
- 3,479 Sq Ft
- $480/SF
- 6 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2011
22 Graystone Cir Unit 22, Winchester, MA 01890

Discover luxury & convenience in this beautifully maintained 2-3 bed, 2.5-baths end unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering first floor primary suite! The gourmet kitchen showcases custom maple cabinetry, granite countertops, top-of-the-line stainless steel appliances, induction cooking & gleaming hardwood floors. The

Kim Covino Compass

22 Graystone Cir Unit 22, Winchester, MA 01890

/42
Est $1,852,301 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,131 Sq Ft
39 Wildwood St, Winchester, MA 01890

39 Wildwood St, Winchester, MA 01890

/42
$2,035,000 Sold Nov 19, 2024
- 4,730 Sq Ft
- $430/SF
- 12 Days On Market
- 5 Beds
- 4 Baths
- Built 1953
43 Emerson Rd, Winchester, MA 01890

See it to believe it! Don’t miss this sprawling 5 bed, 4 full bath Cape-style home in an idyllic Ambrose school neighborhood. 1st floor features mudroom w/entry from attached garage, laundry room w/sink, living room w/fireplace, bedroom, full bath, & dining area w/French doors to a deck. But the jewel of this floor is the recent addition of a stunning eat-in kitchen & sun-filled primary suite.

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

43 Emerson Rd, Winchester, MA 01890

/40
Est $2,673,182 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

/41
$1,800,000 Sold Nov 18, 2024
- 3,866 Sq Ft
- $466/SF
- 5 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1905
118 Forest St, Winchester, MA 01890

This thoughtfully updated home combines historic charm and modern style. The oversized, beautifully landscaped lot showcases established plantings, charming stone paths, and terraced gardens - the perfect oasis for relaxing family time and outdoor entertaining. Inside, the hub of this 5 BR, 3,5 BA home is the large, open-concept kitchen and family room, featuring a cathedral ceiling, gas

Jay Smith Brad Hutchinson Real Estate

118 Forest St, Winchester, MA 01890

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