Winchester, MA Homes

/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

/19
$690,000 Sold Jun 06, 2025
- 1,634 Sq Ft
- $422/SF
- 20 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1999
7 Conant Rd Unit 60, Winchester, MA 01890

OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and

Irene Novia Loka Matahari Real Estate LLC

7 Conant Rd Unit 60, 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

/33
$1,650,000 Sold Jun 06, 2025
- 3,338 Sq Ft
- $494/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
34 Coolidge Rd, Winchester, MA 01890

A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

Pauline Marino Coldwell Banker Realty - Lexington

34 Coolidge 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

/38
$1,475,000 Sold Jun 05, 2025
- 2,897 Sq Ft
- $509/SF
- 15 Days On Market
- 4 Beds
- 3 Baths
- Built 1934
195 Mystic Valley Pkwy, Winchester, MA 01890

Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

195 Mystic Valley Pkwy, 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
$2,111,000 Sold Jun 05, 2025
- 4,744 Sq Ft
- $445/SF
- 6 Days On Market
- 5 Beds
- 4 Baths
- Built 1922
14 Grove St, Winchester, MA 01890

Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

Kim Covino Compass

14 Grove St, Winchester, MA 01890

/42
Est $945,598 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,317 Sq Ft
83 Church St Unit 14, Winchester, MA 01890

83 Church St Unit 14, Winchester, MA 01890

/11
$1,269,000 Sold Jun 04, 2025
- 2,136 Sq Ft
- $594/SF
- 1 Day On Market
- 3 Beds
- 3.5 Baths
- Built 2025
158 Swanton St Unit 160, Winchester, MA 01890

Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

Monte Marrocco Coldwell Banker Realty - Lexington

158 Swanton St Unit 160, Winchester, MA 01890

/32
Est $971,208 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,493 Sq Ft
83 Church St Unit 6, Winchester, MA 01890

83 Church St Unit 6, Winchester, MA 01890

/24
$1,084,000 Sold Jun 04, 2025
- 2,290 Sq Ft
- $473/SF
- 30 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2025
160 Swanton St Unit 160, Winchester, MA 01890

Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

Monte Marrocco Coldwell Banker Realty - Lexington

160 Swanton St Unit 160, Winchester, MA 01890

/22
Est $1,598,053 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,782 Sq Ft
13 Wildwood St, Winchester, MA 01890

13 Wildwood St, Winchester, MA 01890

/26
$1,140,000 Sold Jun 03, 2025
- 1,646 Sq Ft
- $693/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
7 Indian Hill Rd, Winchester, MA 01890

This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a

Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

7 Indian Hill Rd, Winchester, MA 01890

/42
Est $1,944,061 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,765 Sq Ft
44 Church St, Winchester, MA 01890

44 Church St, Winchester, MA 01890

/34
$2,000,000 Sold Jun 02, 2025
- 3,039 Sq Ft
- $658/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1927
11 Chesterford Rd E, Winchester, MA 01890

Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

Joseph Pollack Redfin Corp.

11 Chesterford Rd E, Winchester, MA 01890

/24
Est $1,718,793 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,572 Sq Ft
60 Church St, Winchester, MA 01890

60 Church St, Winchester, MA 01890

/33
$699,900 Sold May 30, 2025
- 1,326 Sq Ft
- $528/SF
- 4 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1890
32 Clark St, Winchester, MA 01890

A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

Rodrigo Serrano Leading Edge Real Estate

32 Clark St, Winchester, MA 01890

/42
Est $4,004,964 Not Listed For Sale
- 6 Beds
- 6.5 Baths
- 8,178 Sq Ft
3 Ravine Rd, Winchester, MA 01890

3 Ravine Rd, Winchester, MA 01890

/42
$1,350,000 Sold May 30, 2025
- 3,351 Sq Ft
- $403/SF
- 38 Days On Market
- 3 Beds
- 4 Baths
- Built 1946
34 Fells Rd, Winchester, MA 01890

Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

Andersen Group Realty Keller Williams Realty Boston Northwest

34 Fells Rd, Winchester, MA 01890

/31
Est $1,997,535 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,769 Sq Ft
23 Ravine Rd, Winchester, MA 01890

23 Ravine Rd, Winchester, MA 01890

/37
$1,450,000 Sold May 30, 2025
- 3,763 Sq Ft
- $385/SF
- 34 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
7 Wainwright Rd Unit 8, Winchester, MA 01890

Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

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

7 Wainwright Rd Unit 8, Winchester, MA 01890

/36
Est $1,770,022 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,421 Sq Ft
28 Fletcher St, Winchester, MA 01890

28 Fletcher St, Winchester, MA 01890

/25
$1,881,900 Sold May 30, 2025
- 3,488 Sq Ft
- $540/SF
- 34 Days On Market
- 4 Beds
- 4 Baths
- Built 1980
4 Olde Lyme Rd, Winchester, MA 01890

This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for

Nancy Pallotta Gibson Sotheby's International Realty

4 Olde Lyme Rd, Winchester, MA 01890

/38
Est $1,415,000 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 2,465 Sq Ft
82 Church St Unit 84, Winchester, MA 01890

82 Church St Unit 84, Winchester, MA 01890

/42
$1,558,000 Sold May 29, 2025
- 2,792 Sq Ft
- $558/SF
- 9 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1993
24 Eugene Dr, Winchester, MA 01890

Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

Andrea O'Reilly Keller Williams Realty Evolution

24 Eugene Dr, Winchester, MA 01890

/42
Est $2,248,254 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,979 Sq Ft
12 Norwood St, Winchester, MA 01890

12 Norwood St, Winchester, MA 01890

/31
$948,000 Sold May 29, 2025
- 1,469 Sq Ft
- $645/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1928
79 Sylvester Ave, Winchester, MA 01890

Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention

Anne Spry Barrett Sotheby's International Realty

79 Sylvester Ave, Winchester, MA 01890

/36
Est $2,070,007 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,688 Sq Ft
6 Harrington Rd, Winchester, MA 01890

6 Harrington Rd, Winchester, MA 01890

/31
$380,000 Sold May 23, 2025
- 613 Sq Ft
- $620/SF
- 15 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
200 Swanton St Unit 722, Winchester, MA 01890

Top-Floor Penthouse Condo with Scenic Views at Parkview Condominiums Move right into this beautifully updated 1-bedroom, 1-bath top-floor unit at the highly desirable Parkview Condominiums in Winchester. Centrally located on the 7th floor, this penthouse offers stunning treetop and pond views from your private balcony—perfect for enjoying peaceful moments all year round. Inside, you'll find a

Yang Liu Weston Realty LLC

200 Swanton St Unit 722, Winchester, MA 01890

/35
Est $2,566,671 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,453 Sq Ft
73 Bacon St, Winchester, MA 01890

73 Bacon St, Winchester, MA 01890

/33
$1,785,000 Sold May 22, 2025
- 2,848 Sq Ft
- $627/SF
- 13 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1968
85 Thornberry Rd, Winchester, MA 01890

Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area

Diane Basemera Coldwell Banker Realty - Newton

85 Thornberry Rd, Winchester, MA 01890

/35
Est $3,196,875 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,981 Sq Ft
59 Bacon St, Winchester, MA 01890

59 Bacon St, Winchester, MA 01890

/42
$2,750,000 Sold May 19, 2025
- 5,263 Sq Ft
- $523/SF
- 12 Days On Market
- 6 Beds
- 6 Baths
- Built 1920
35 Lawson Rd, Winchester, MA 01890

Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning marble mudroom welcomes you into the home w/ heated floors leading into fabulous new custom kitchen featuring a large dining island, inset cabinets, Wolf/Sub-Zero appliances (2 dishwashers, 2 ovens/ steam oven, 2 fridge drawers) a sleek gas fireplace, built-in banquette & direct

Kim Covino Compass

35 Lawson Rd, Winchester, MA 01890

/42
Est $1,358,617 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,647 Sq Ft
4 Rangeley Rd Unit 4A, Winchester, MA 01890

4 Rangeley Rd Unit 4A, Winchester, MA 01890

/42
$2,499,000 Sold May 19, 2025
- 4,270 Sq Ft
- $585/SF
- 0 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
50 Winford Way, Winchester, MA 01890

Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

Kim Covino Compass

50 Winford Way, Winchester, MA 01890

/42
Est $2,067,173 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,746 Sq Ft
2 Fairfield Place, Winchester, MA 01890

2 Fairfield Place, 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 $1,369,586 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,734 Sq Ft
30 Middlesex St, Winchester, MA 01890

30 Middlesex St, Winchester, MA 01890

/42
$4,065,000 Sold May 16, 2025
- 7,500 Sq Ft
- $542/SF
- 71 Days On Market
- 6 Beds
- 7.5 Baths
- Built 2025
6 Vinson Cir, Winchester, MA 01890

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances,

Peter Kasseris Compass

6 Vinson Cir, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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