Winchester, MA Homes

/31
Est $1,168,390 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,321 Sq Ft
23 New Meadows Rd, Winchester, MA 01890

23 New Meadows Rd, Winchester, MA 01890

/25
$724,900 Pending
- 2 Beds
- 2.5 Baths
- 1,539 Sq Ft
7 Conant Rd Unit 37, Winchester, MA 01890

Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace w/marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience,

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

7 Conant Rd Unit 37, 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

/37
Est $1,377,020 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,386 Sq Ft
15 New Meadows Rd, Winchester, MA 01890

15 New Meadows Rd, Winchester, MA 01890

/39
$1,425,000 Pending
- 3 Beds
- 2.5 Baths
- 2,282 Sq Ft
20 Fletcher St Unit 20, Winchester, MA 01890

Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! W its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication throughout.

Kim Covino Compass

20 Fletcher St Unit 20, 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

/25
Est $1,571,497 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,139 Sq Ft
11 New Meadows Rd, Winchester, MA 01890

11 New Meadows Rd, Winchester, MA 01890

/42
$1,399,000 Pending
- 3 Beds
- 2.5 Baths
- 2,141 Sq Ft
117 Mount Vernon St, Winchester, MA 01890

Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining

Philip Vita Compass

117 Mount Vernon St, 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

/36
Est $1,781,695 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,432 Sq Ft
21 Westland Ave, Winchester, MA 01890

21 Westland Ave, Winchester, MA 01890

/32
$1,199,000 Pending
- 3 Beds
- 2 Baths
- 1,978 Sq Ft
48 Winford Way, Winchester, MA 01890

Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family

Rebecca Brennan Better Homes and Gardens Real Estate - The Shanahan Group

48 Winford Way, 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

/40
Est $1,732,586 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,414 Sq Ft
23 Westland Ave, Winchester, MA 01890

23 Westland Ave, Winchester, MA 01890

/28
$724,999 Pending
- 2 Beds
- 2 Baths
- 1,170 Sq Ft
666 Main St Unit 206, Winchester, MA 01890

Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban convenience. This desirable and well-maintained 2 bed/2 bath home comes with 1 covered parking. Enjoy a spacious open-concept layout with a wood-burning fireplace, screened-in balcony overlooking courtyard & pool, and updated kitchen and guest bath. The oversized primary suite offers

Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

666 Main St Unit 206, 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

/41
Est $2,750,177 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,100 Sq Ft
14 Seneca Rd, Winchester, MA 01890

14 Seneca Rd, Winchester, MA 01890

/42
$2,349,900 Pending
- 5 Beds
- 5 Baths
- 3,940 Sq Ft
17 Wagon Wheel Rd, Winchester, MA 01890

Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

Dream Team Dreamega International Realty LLC

17 Wagon Wheel Rd, 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

/42
Est $2,787,621 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 5,315 Sq Ft
6 Agawam Rd, Winchester, MA 01890

6 Agawam Rd, Winchester, MA 01890

/25
$1,050,000 Pending
- 3 Beds
- 3 Baths
- 2,534 Sq Ft
8 Ware Rd, Winchester, MA 01890

Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern

Alex Navarro Coldwell Banker Realty - Beverly

8 Ware Rd, 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

/39
Est $1,644,077 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,428 Sq Ft
21 Samoset Rd, Winchester, MA 01890

21 Samoset Rd, Winchester, MA 01890

/32
$1,300,000 Pending
- 5 Beds
- 3.5 Baths
- 2,137 Sq Ft
18 Hemingway St, Winchester, MA 01890

This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

Julia Xie Keller Williams Realty-Merrimack

18 Hemingway St, 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

/28
Est $1,791,353 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,800 Sq Ft
5 Manomet Rd, Winchester, MA 01890

5 Manomet Rd, Winchester, MA 01890

/42
$1,525,000 Pending
- 4 Beds
- 2.5 Baths
- 2,814 Sq Ft
21 Johnson Rd, Winchester, MA 01890

This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The

Stefanie Clifford Keller Williams Realty Boston Northwest

21 Johnson Rd, 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

/36
Est $2,322,299 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,871 Sq Ft
111 Arlington St, Winchester, MA 01890

111 Arlington St, Winchester, MA 01890

/32
$1,065,000 Pending
- 4 Beds
- 1.5 Baths
- 2,349 Sq Ft
25 Canterbury Rd, Winchester, MA 01890

Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spacious living room with built-ins, four, second floor bedrooms, and an expansive .37 acre lot. The versatile family room provides flexible space for a home office, playroom, or guest space! Imagine evenings on the covered porch or patio,

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

25 Canterbury Rd, 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

/41
Est $2,980,752 Not Listed For Sale
- 5 Beds
- 7 Baths
- 5,830 Sq Ft
108 Arlington St, Winchester, MA 01890

108 Arlington St, Winchester, MA 01890

/42
$1,699,000 Pending
- 3 Beds
- 4 Baths
- 2,646 Sq Ft
50 Johnson Rd, Winchester, MA 01890

One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

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

50 Johnson 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 $2,195,725 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,400 Sq Ft
20 Westland Ave, Winchester, MA 01890

20 Westland Ave, Winchester, MA 01890

/41
$1,499,000 Pending
- 3 Beds
- 2.5 Baths
- 2,189 Sq Ft
23 Elmwood Ave Unit C, Winchester, MA 01890

Welcome to Elmwood condos with over 2,100 SF of stunning single-level luxury living in vibrant downtown Winchester! This sparkling, modern condo offers a beautifully open floor plan designed for today's discerning buyer with the kitchen, dining & living areas seamlessly integrated for both comfort and style. Enjoy high end/ top-of-the-line, rich finishes throughout, including gleaming hardwood

Kim Covino Compass

23 Elmwood Ave Unit C, 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

/40
Est $1,849,886 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,205 Sq Ft
8 Sachem Rd, Winchester, MA 01890

8 Sachem Rd, Winchester, MA 01890

/42
$2,400,000 Pending
- 5 Beds
- 4.5 Baths
- 4,215 Sq Ft
12 Olde Lyme Rd, Winchester, MA 01890

*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

Mary Beth McGillicuddy Engel & Völkers , South Shore

12 Olde Lyme Rd, Winchester, MA 01890
/32
$995,000 Sold Dec 23, 2024
- 1,275 Sq Ft
- $780/SF
- 7 Days On Market
- 1 Bed
- 2 Baths
- Built 2017
15 Dix St Unit 9, Winchester, MA 01890

Get ready to enjoy one level living with elevator access from heated garage with 2 exclusive use parking spots. This is the place to be for LOCATION, LOCATION, LOCATION AND GARAGE PARKING!!! Inviting, open floor plan features hardwood flooring, large windows, and a generous amount of storage space. Kitchen features large marble topped island with counter seating, gas range and Sub Zero

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

15 Dix St Unit 9, Winchester, MA 01890

/40
Est $1,566,305 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,071 Sq Ft
10 Westland Ave, Winchester, MA 01890

10 Westland Ave, Winchester, MA 01890

Showing Results 241 - 280, Page 7 of 18

Massachusetts Winchester

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