Winchester, MA Homes

/4
$3,799,900
- 7 Beds
- 7.5 Baths
- 7,429 Sq Ft
11 Viking Rd, Winchester, MA 01890

Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

The McLaren D'Agostino Team Compass

11 Viking Rd, Winchester, MA 01890
/42
$2,799,000 Sold Jan 30, 2025
- 4,324 Sq Ft
- $647/SF
- 68 Days On Market
- 5 Beds
- 6 Baths
- Built 1938
16 Ardley Place, Winchester, MA 01890

Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation areas & seasonal views of Winter Pond. Featuring 5 Bed,4 Full baths, 2-half with 2 ensuites plus a

16 Ardley Place, Winchester, MA 01890

/38
Est $1,749,721 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,218 Sq Ft
27 Amberwood Dr, Winchester, MA 01890

27 Amberwood Dr, Winchester, MA 01890

/22
$1,295,000
- 4 Beds
- 1.5 Baths
- 2,202 Sq Ft
71 Woodside Rd, Winchester, MA 01890

Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation,

Jorge Rodriguez Carlton's Wharf & Co.

71 Woodside Rd, Winchester, MA 01890
/38
$1,900,000 Sold Jan 29, 2025
- 3,611 Sq Ft
- $526/SF
- 50 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1984
11 Plymouth Rd, Winchester, MA 01890

OPEN HOUSE SUNDAY 11/17 11:30-1:00pm. Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointed dining room with custom built-in China cabinet is perfect for large

Darryl Brian RE/MAX Bentley's

11 Plymouth Rd, Winchester, MA 01890

/42
Est $2,361,229 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,016 Sq Ft
22 Amberwood Dr, Winchester, MA 01890

22 Amberwood Dr, Winchester, MA 01890

/39
$2,499,000
- 6 Beds
- 3.5 Baths
- 4,667 Sq Ft
9 Prospect St, Winchester, MA 01890

Step into a piece of history with this incredibly charming 1895 Colonial Revival, a home that exudes elegance, character, and masterful craftsmanship at every turn. From the moment you arrive, you’ll be captivated by its stately presence, classic architectural details, and warm, inviting ambiance. Inside, you’ll find an extraordinary blend of historic charm and modern livability.The craftsmanship

Nancy Pallotta Advisors Living - Winchester

9 Prospect St, Winchester, MA 01890
/33
$642,000 Sold Jan 28, 2025
- 1,752 Sq Ft
- $366/SF
- 56 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1880
20 Hancock St, Winchester, MA 01890

Welcome to Winchester ! This townhouse with large shared backyard is located on lovely tree lined street . The front porch welcomes you as you can sit and watch the world go by. First floor has living room, dining room and kitchen with laundry. Half bath completes the first floor. Three bedrooms and full bath upstairs. One bedroom is a pass through. Back stairway to half of full size attic is off

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

20 Hancock St, Winchester, MA 01890

/42
Est $2,162,972 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,124 Sq Ft
9 Buckman Dr, Winchester, MA 01890

9 Buckman Dr, Winchester, MA 01890

/16
$1,199,000
- 4 Beds
- 2 Baths
- 2,621 Sq Ft
61 Westland Ave, Winchester, MA 01890

Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

61 Westland Ave, Winchester, MA 01890
/38
$2,199,000 Sold Jan 27, 2025
- 3,431 Sq Ft
- $641/SF
- 21 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
11 Alden Ln, Winchester, MA 01890

This stunning new 4 Bed 3.5 BA home in Winchester’s sought-after East Side is a must see! The first floor boasts a dramatic contemporary design with high ceilings and designer finishes with oversized windows drawing attention to the setting w/ large rear yard & oversized deck, great for entertaining and family enjoyment.The open airy layout features a great entry w/ mud room, high-end kitchen

Kim Covino Compass

11 Alden Ln, Winchester, MA 01890

/42
Est $1,831,521 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
3 Bigelow Ave, Winchester, MA 01890

3 Bigelow Ave, Winchester, MA 01890

/42
$1,389,000 Open Sat 12PM - 1PM
- 3 Beds
- 4 Baths
- 3,351 Sq Ft
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
/30
$2,050,000 Sold Jan 24, 2025
- 3,450 Sq Ft
- $594/SF
- 89 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1953
9 South Gateway, Winchester, MA 01890

Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath

Mark Donnellan Advisors Living - Winchester

9 South Gateway, Winchester, MA 01890

/42
Est $2,079,578 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,256 Sq Ft
15 Pilgrim Dr, Winchester, MA 01890

15 Pilgrim Dr, Winchester, MA 01890

/41
$3,199,000
- 6 Beds
- 5 Baths
- 5,198 Sq Ft
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
/42
$1,517,500 Sold Jan 09, 2025
- 3,091 Sq Ft
- $491/SF
- 7 Days On Market
- 6 Beds
- 3 Baths
- Built 1957
14 Henry St, Winchester, MA 01890

Incredible value! Don’t miss this 6 BR, 3 full bathroom expanded colonial w/ over 3,000 square feet of living space tucked away in a charming Vinson Owen School neighborhood. This expansive home features an open concept, eat-in kitchen/family room w/ granite countertops, double ovens, large island, recessed lighting & cozy family room. The sunny kitchen also opens to a private backyard w/ stone

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

14 Henry St, Winchester, MA 01890

/40
Est $1,480,815 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
16 Johnson Rd, Winchester, MA 01890

16 Johnson Rd, Winchester, MA 01890

/42
$2,850,000
- 4 Beds
- 3 Baths
- 4,276 Sq Ft
8 Tanglewood Ln, Winchester, MA 01890

This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

Kim Covino Compass

8 Tanglewood Ln, Winchester, MA 01890
/42
$1,130,000 Sold Jan 08, 2025
- 1,883 Sq Ft
- $600/SF
- 21 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1948
6 Governors Ave, Winchester, MA 01890

Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dining room; updated kitchen overlooks the rear yard & is equipped w/ ample storage, stainless steel

Kim Covino Compass

6 Governors Ave, Winchester, MA 01890

/31
Est $1,811,454 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,256 Sq Ft
11 Olde Lyme Rd, Winchester, MA 01890

11 Olde Lyme Rd, Winchester, MA 01890

/42
$2,399,000 Open Sat 11AM - 12PM
- 5 Beds
- 3.5 Baths
- 5,077 Sq Ft
276 High St, Winchester, MA 01890

This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase

Andersen Group Realty Keller Williams Realty Boston Northwest

276 High St, Winchester, MA 01890
/32
$1,080,000 Sold Jan 08, 2025
- 3,220 Sq Ft
- $335/SF
- 105 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1900
89 Mystic Valley Pkwy, Winchester, MA 01890

Price Adjustment to Assessed Value!! Victorian townhome in fabulous downtown location! Ideally situated in close proximity to trains, schools, restaurants and everything Winchester Center has to offer! Front porch welcomes you into this lovingly cared for home blending old world charm with modern amenities. First floor features high ceilings, beautiful hardwood flooring, fireplaced living room

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

89 Mystic Valley Pkwy, Winchester, MA 01890

/42
Est $2,361,499 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,473 Sq Ft
239 Ridge St, Winchester, MA 01890

239 Ridge St, Winchester, MA 01890

/40
$3,149,000 Open Sat 1PM - 2PM
- 7 Beds
- 5.5 Baths
- 6,200 Sq Ft
10 Sheffield Rd, Winchester, MA 01890

This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

Andersen Group Realty Keller Williams Realty Boston Northwest

10 Sheffield Rd, Winchester, MA 01890
/33
$1,542,500 Sold Jan 07, 2025
- 3,588 Sq Ft
- $430/SF
- 62 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2011
58 Graystone Cir Unit 58, Winchester, MA 01890

Discover this like-new three bedroom, 3.5 bathroom property, originally purchased as a model unit with numerous high-end upgrades and impeccably maintained since. Soaring ceilings in the first-floor family room create a bright, airy space perfect for entertaining. The open-concept layout seamlessly flows from the designer kitchen area through to dining room and living room, with french doors to

Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

58 Graystone Cir Unit 58, Winchester, MA 01890

/26
Est $1,164,396 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,826 Sq Ft
75 Dunster Ln, Winchester, MA 01890

75 Dunster Ln, Winchester, MA 01890

/34
$3,698,000
- 6 Beds
- 7 Baths
- 8,866 Sq Ft
20 Amberwood Dr, Winchester, MA 01890

Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

Dan Li Keller Williams Realty

20 Amberwood Dr, Winchester, MA 01890
/21
$425,000 Sold Jan 03, 2025
- 758 Sq Ft
- $561/SF
- 9 Days On Market
- 1 Bed
- 1 Bath
- Built 1982
64 Highland Ave Unit 18, Winchester, MA 01890

DON'T MISS THIS ONE! Ideal location at Waterfield Square - This spacious one bedroom is a diamond-in-the-rough waiting for your upgrades. High ceilings and huge windows bring in lots of sun and light. Open floor plan. Lots of closet space. Washer & Dryer in unit. Deeded parking, basement storage, tennis court, picnic area with grill, fire pit, located across from the North Reservoir and

Diane Plunkett Plunkett Properties

64 Highland Ave Unit 18, Winchester, MA 01890

/42
Est $3,165,164 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,676 Sq Ft
222 High St, Winchester, MA 01890

222 High St, Winchester, MA 01890

/40
$2,695,000
- 4 Beds
- 4.5 Baths
- 5,233 Sq Ft
18 Middlesex St, Winchester, MA 01890

A masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and exquisite finishes. The Bespoke

Candice Macoul Luxury Living Real Estate

18 Middlesex St, Winchester, MA 01890
/29
$1,335,000 Sold Dec 27, 2024
- 2,245 Sq Ft
- $595/SF
- 117 Days On Market
- 4 Beds
- 2 Baths
- Built 1959
28 Thornberry Rd, Winchester, MA 01890

Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining,

Shaundize Moosavizadeh Coldwell Banker Realty - Boston

28 Thornberry Rd, Winchester, MA 01890

/27
Est $1,034,689 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
46 Edward Dr, Winchester, MA 01890

46 Edward Dr, Winchester, MA 01890

/42
$3,989,000
- 6 Beds
- 6.5 Baths
- 8,463 Sq Ft
26 Swan Rd, Winchester, MA 01890

Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

Kim Covino Compass

26 Swan Rd, Winchester, MA 01890
/39
$1,450,000 Sold Dec 26, 2024
- 1,969 Sq Ft
- $736/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1950
37 Tufts Rd, Winchester, MA 01890

Beautifully renovated home with open concept main living area including elegantly updated kitchen with quartz countertops, professional grade range and wine refrigerator. Primary suite includes cathedral ceilings and oversized (8' high) sliders opening up to private balcony with views of Leonard Pond. His and hers closets and private bath with double sinks and radiant heat make this the perfect

Amanda Armstrong Compass

37 Tufts Rd, Winchester, MA 01890

/42
Est $1,013,990 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,738 Sq Ft
41 Edward Dr, Winchester, MA 01890

41 Edward Dr, Winchester, MA 01890

/42
$2,999,000
- 5 Beds
- 6 Baths
- 5,354 Sq Ft
8 Chestnut St, Winchester, MA 01890

Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

The McLaren D'Agostino Team Compass

8 Chestnut St, Winchester, MA 01890
/36
$1,025,000 Sold Dec 23, 2024
- 3,045 Sq Ft
- $337/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 1986
22 Grove Place Unit 30, Winchester, MA 01890

Welcome to 22 Grove Place Unit 30, a 3-bedroom, 3-bathroom townhouse in Winchester, MA, that combines single-family privacy with the ease of townhouse living. This home just had the walls and ceilings freshly painted, along with new light fixtures that add a modern touch. The main level offers a spacious living room with high ceilings, a cozy double sided gas fireplace, a home office, first floor

Peter Kasseris Coldwell Banker Realty - Lexington

22 Grove Place Unit 30, Winchester, MA 01890

/38
Est $1,041,916 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
34 Edward Dr, Winchester, MA 01890

34 Edward Dr, Winchester, MA 01890

/37
$699,900
- 2 Beds
- 2 Baths
- 1,168 Sq Ft
7 Conant Rd Unit 20, Winchester, MA 01890

Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

Brian Woods Woods Properties Inc.

7 Conant Rd Unit 20, Winchester, MA 01890

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