Winchester, MA Homes

/42
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

/34
$2,960,000 Sold Dec 12, 2024
- 4,860 Sq Ft
- $609/SF
- 72 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
39 Everett Ave, Winchester, MA 01890

Welcome to this stunning, brand-new construction in Winchester's most desired neighborhood. This home offers modern luxury and timeless elegance. The custom kitchen features two-toned countertops with a Pegasus marble island and Jet Mist granite perimeter, along with brass accents. The pantry provides for ample additional storage with floor to ceiling cabinets, jet mist counters and a wine

Mark Donnellan Gibson Sotheby's International Realty

39 Everett Ave, Winchester, MA 01890

/24
Est $1,173,144 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

/37
$2,750,000 Sold Dec 12, 2024
- 4,212 Sq Ft
- $653/SF
- 21 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1935
56 Salisbury St, Winchester, MA 01890

Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats,

The McLaren D'Agostino Team Compass

56 Salisbury St, Winchester, MA 01890

/34
Est $1,042,544 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,918 Sq Ft
5 Bates Rd, Winchester, MA 01890

5 Bates Rd, Winchester, MA 01890

/38
$1,650,000 Sold Dec 11, 2024
- 3,158 Sq Ft
- $522/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1975
31 Girard Rd, Winchester, MA 01890

Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

Philip Vita Compass

31 Girard Rd, Winchester, MA 01890

/35
Est $1,216,094 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

/42
$1,755,000 Sold Dec 10, 2024
- 2,886 Sq Ft
- $608/SF
- 7 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1911
19 Warren St, Winchester, MA 01890

Step into this beautifully designed 3-bedroom, 3-bathroom single-family home located in the sought-after Flats of Winchester. Nestled in a wonderful neighborhood, this home offers a perfect blend of charm and modern living. The spacious living room with a cozy fireplace flows seamlessly into a bright sunroom, filling the space with natural light. The eat-in kitchen is equipped with stainless

Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

19 Warren St, Winchester, MA 01890

/34
Est $1,145,970 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

/40
$1,225,000 Sold Dec 09, 2024
- 3,350 Sq Ft
- $366/SF
- 27 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
7 Wainwright Rd Unit 29, Winchester, MA 01890

Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

Joanne Sexeny Coldwell Banker Realty - Lexington

7 Wainwright Rd Unit 29, Winchester, MA 01890

/39
Est $1,072,103 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
29 Harvard St, Winchester, MA 01890

29 Harvard St, Winchester, MA 01890

/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 Gibson Sotheby's International Realty

63-65 Harvard St, Winchester, MA 01890

/33
Est $952,372 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

/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

/26
Est $1,071,432 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,886 Sq Ft
11 Swanton St, Winchester, MA 01890

11 Swanton St, 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

/18
Est $934,272 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
22 Chester St, Winchester, MA 01890

22 Chester St, 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 Gibson Sotheby's International Realty

25 Ledgewood Rd, Winchester, MA 01890

/30
Est $1,700,715 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,181 Sq Ft
68 Harvard St, Winchester, MA 01890

68 Harvard 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

/19
Est $850,036 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,292 Sq Ft
18 Olive St, Winchester, MA 01890

18 Olive St, 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

/10
Est $1,634,226 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,050 Sq Ft
30 Florence St, Winchester, MA 01890

30 Florence St, 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 Gibson Sotheby's International Realty

78 Middlesex St, Winchester, MA 01890

/39
Est $1,168,101 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,660 Sq Ft
246 Washington St, Winchester, MA 01890

246 Washington St, 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

/19
Est $378,629 Not Listed For Sale
- 1 Bed
- 1 Bath
- 613 Sq Ft
200 Swanton St Unit 728, Winchester, MA 01890

200 Swanton St Unit 728, 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

/30
Est $400,000 Not Listed For Sale
- 1 Bed
- 1 Bath
- 700 Sq Ft
200 Swanton St Unit 721, Winchester, MA 01890

200 Swanton St Unit 721, 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

/30
Est $308,434 Not Listed For Sale
- 1 Bed
- 1 Bath
- 394 Sq Ft
200 Swanton St Unit 702, Winchester, MA 01890

200 Swanton St Unit 702, 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
$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

/31
Est $390,221 Not Listed For Sale
- 1 Bed
- 1 Bath
- 613 Sq Ft
200 Swanton St Unit 632, Winchester, MA 01890

200 Swanton St Unit 632, 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

/41
Est $392,550 Not Listed For Sale
- 1 Bed
- 1 Bath
- 613 Sq Ft
200 Swanton St Unit 627, Winchester, MA 01890

200 Swanton St Unit 627, 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

/17
Est $384,596 Not Listed For Sale
- 1 Bed
- 1 Bath
- 618 Sq Ft
200 Swanton St Unit 514, Winchester, MA 01890

200 Swanton St Unit 514, 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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Massachusetts Middlesex County Winchester

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