Winchester, MA homes for sale & real estate

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30 Swan Rd, Winchester, MA 01890
30 Swan Rd, Winchester, MA 01890
30 Swan Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Discover the prestige of owning a home at 30 Swan Road, a distinguished Tudor-style residence on one of Winchester's most esteemed streets. Offering magnificent grounds and an impressive brick exterior complemented by a slate roof, this property sets the tone for the elegance within. It's perfect for a buyer looking to add sweat equity or a contractor seeking a rewarding project. Upon entering, you're greeted by a grand foyer that captivates with its sophistication. The living room boasts an exquisite fireplace and handcrafted wood walls, while the 1st floor also includes a sunlit sitting room, a dedicated office, a sunroom, and a dining room. Experience the timeless opulence and grandeur o

$2,500,000

6 beds4.5 baths4,323 sq ft

30 Swan Rd, Winchester, MA 01890

0.85 acre lot • 3 garage spots • Community pool

7 Conant Rd #20, Winchester, MA 01890
7 Conant Rd #20, Winchester, MA 01890
7 Conant Rd #20, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, single-level unit features an open-concept living area with new hardwood flooring, a versatile space that can be used as a dining room, home office or home entertainment alcove and a cozy gas fireplace. The updated kitchen features fresh granite countertops and brand new appliances. Delight in the spacious primary bedroom that features a refreshed en-suite bath and full walk-in closet. The amply sized second bedroom also has a walk-in closet. The unit is complete with a second enhanced full bathroom, central AC, in-unit laundry, and an enclosed patio. The detached ga

$725,000

2 beds2 baths1,168 sq ft

7 Conant Rd #20, Winchester, MA 01890

$611 HOA • Garage • Community pool

3D WALKTHROUGH

19 Laurel Hill Ln, Winchester, MA 01890
19 Laurel Hill Ln, Winchester, MA 01890
19 Laurel Hill Ln, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
Nestled in a desirable neighborhood, this home offers the opportunity to embrace the timeless elegance of the mid-century era. Lovingly maintained in its original condition, the ranch style provides the coveted option for one-level living. Enter the main level into the fireplaced living room, with large picture window and hardwood floors. Adjacent to the kitchen is the dining room with hardwood floors and window peeking into the family room, flooded with natural light and a cozy wood stove. Three comfortable bedrooms and full bath complete the main level. Additional features include the unfinished lower level with 3/4 bath, offering opportunity for additional finished space, and the conveni

$995,000

3 beds2 baths1,638 sq ft

19 Laurel Hill Ln, Winchester, MA 01890

0.31 acre lot • Garage • Car-dependent

NEW CONSTRUCTION3D & VIDEO TOUR

158 Swanton St #158, Winchester, MA 01890
158 Swanton St #158, Winchester, MA 01890
158 Swanton St #158, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
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 appliances, a spacious island, and an adjacent mudroom with a half bath. The second floor offers two bedrooms and a full bath, while the third floor is a private primary suite with a spa-like en-suite. The finished lower level provides a versatile space—ideal as a great room, office, or gym

$1,269,000

3 beds3.5 baths2,136 sq ft

158 Swanton St #158, Winchester, MA 01890

$237 HOA • Somewhat walkable

4 Olde Lyme Rd, Winchester, MA 01890
4 Olde Lyme Rd, Winchester, MA 01890
4 Olde Lyme Rd, Winchester, MA 01890
ABOUT THIS HOME
Winchester, MA Homes for Sale
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 entertaining. ! Hardwood floors highlight the main living area and bedrooms, working as a perfect offset to all the natural light this home enjoys. There's a cozy den with a wet bar/entertainment area plus a huge family room in the lower level. The primary suite is a private retreat with a spa-like bath

$1,899,000

4 beds4 baths3,488 sq ft

4 Olde Lyme Rd, Winchester, MA 01890

0.35 acre lot • 2 garage spots • Car-dependent

Property at 5 Pine St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,250,000

5 beds3.5 baths4,273 sq ft

5 Pine St, Winchester, MA 01890

Property at 5 Woodside Rd, Winchester, MA 01890, 6 beds, 2.5 baths

$2,199,000

6 beds2.5 baths3,487 sq ft

5 Woodside Rd, Winchester, MA 01890

Property at 21 Sheffield West, Winchester, MA 01890, 6 beds, 4 baths

$3,499,000

6 beds4 baths5,198 sq ft

21 Sheffield West, Winchester, MA 01890

Property at 54 Johnson Rd, Winchester, MA 01890, 7 beds, 7.5 baths

$3,999,000

7 beds7.5 baths7,982 sq ft

54 Johnson Rd, Winchester, MA 01890

Property at 5 Clearwater Rd, Winchester, MA 01890, 6 beds, 7.5 baths

$2,899,000

6 beds7.5 baths5,658 sq ft

5 Clearwater Rd, Winchester, MA 01890

Property at 4 Norwood St, Winchester, MA 01890, 5 beds, 4.5 baths

$3,599,000

5 beds4.5 baths5,250 sq ft

4 Norwood St, Winchester, MA 01890

Property at 2 Chestnut St, Winchester, MA 01890, 6 beds, 5 baths

$3,599,000

6 beds5 baths5,500 sq ft

2 Chestnut St, Winchester, MA 01890

Property at 189 Mystic Valley Pkwy, Winchester, MA 01890, 6 beds, 2.5 baths

$1,899,900

6 beds2.5 baths3,543 sq ft

189 Mystic Valley Pkwy, Winchester, MA 01890

Property at 6 Vinson Cir, Winchester, MA 01890, 6 beds, 7.5 baths

$4,199,000

6 beds7.5 baths7,500 sq ft

6 Vinson Cir, Winchester, MA 01890

Property at 7 Wainwright Rd #8, Winchester, MA 01890, 3 beds, 3.5 baths

$1,699,000

3 beds3.5 baths3,763 sq ft

7 Wainwright Rd #8, Winchester, MA 01890

Property at 3 Lagrange St, Winchester, MA 01890, 4 beds, 3.5 baths

$2,699,000

4 beds3.5 baths4,060 sq ft

3 Lagrange St, Winchester, MA 01890

Property at 27 Everett Ave, Winchester, MA 01890, 6 beds, 5.5 baths

$3,799,000

6 beds5.5 baths7,431 sq ft

27 Everett Ave, Winchester, MA 01890

Property at 7 Conant Rd #60, Winchester, MA 01890, 2 beds, 2.5 baths

$749,000

2 beds2.5 baths1,634 sq ft

7 Conant Rd #60, Winchester, MA 01890

Property at 15 Churchill Rd, Winchester, MA 01890, 4 beds, 4.5 baths

$2,699,000

4 beds4.5 baths5,501 sq ft

15 Churchill Rd, Winchester, MA 01890

Property at 50 Winford Way, Winchester, MA 01890, 5 beds, 4.5 baths

$2,599,000

5 beds4.5 baths4,270 sq ft

50 Winford Way, Winchester, MA 01890

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HOT HOME

58 Glenwood Ave, Woburn, MA 01801
58 Glenwood Ave, Woburn, MA 01801
58 Glenwood Ave, Woburn, MA 01801
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome home to this stylish 3-bedroom, 2-bath oasis thoughtfully renovated to exceed Energy Star standards. Improvements include new plumbing, electrical, HVAC, cabinets, fixtures, appliances, energy-efficient windows, spray foam insulation and new pull-down attic stairway. Top floor features 3 comfortable bedrooms, spacious full bath, generously sized LR and modern kitchen flowing into open-concept DR that leads to private back deck ideal for gatherings and relaxing. Large windows flood abundant space with natural light, highlighting sleek new flooring throughout. First-floor FR equipped for entertaining and everyday living with beverage cooler and wet bar. Oversized mudroom leads to atta

$899,900

3 beds1.5 baths1,638 sq ft

58 Glenwood Ave, Woburn, MA 01801

0.33 acre lot • Garage • Car-dependent

18 Garden St, Woburn, MA 01801
18 Garden St, Woburn, MA 01801
18 Garden St, Woburn, MA 01801
ABOUT THIS HOME
Winchester, MA Homes for Sale
A true West Woburn beauty. Well-maintained, updated home in move-in ready condition. Whether you’re an avid gardener or simply enjoy a picturesque yard, this property offers abundant privacy and vibrant blooms throughout Spring, Summer, & Fall, perfect for entertaining. Classic Colonial entry leads to a formal dining room, living room & spacious front-to-back family rm w/ cathedral ceilings, large windows, HW floors, & wood-burning fireplace. Open-concept eat-in kitchen, featuring new stainless appliances, quartzite counters & generous storage, opens to a large rear deck w/ outdoor TV & direct yard access. Upstairs, you’ll find 4bdrm w/ excellent clos

$1,199,900

4 beds2.5 baths3,075 sq ft

18 Garden St, Woburn, MA 01801

0.46 acre lot • 2 garage spots • Car-dependent

HOT HOME

26 Bryant St, Woburn, MA 01801
26 Bryant St, Woburn, MA 01801
26 Bryant St, Woburn, MA 01801
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to this charming 3-bedroom, 1-bath Colonial, perfectly situated on a desirable corner lot. As you step inside, you're greeted by a functional mudroom that serves as a catch-all for everyday essentials. The spacious kitchen boasts ample countertop space, a practical peninsula, and plenty of cabinetry. It seamlessly flows into a cozy yet expansive living room, which opens up to a private deck with serene views of the tranquil backyard. Upstairs, you'll find three comfortable bedrooms and a full bath, while the real surprise awaits on the third level—a hidden bonus space offering endless possibilities. This home also features a convenient two-car driveway and is just a short dist

$549,000

3 beds1 bath1,222 sq ft

26 Bryant St, Woburn, MA 01801

3,485 sq ft lot • Somewhat walkable

HOT HOME

2 Locust Cir, Woburn, MA 01801
2 Locust Cir, Woburn, MA 01801
2 Locust Cir, Woburn, MA 01801
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to 2 Locust Circle, an impeccably-maintained ranch that exudes charm and functionality. Situated on a cul-de-sac in a prime location, this home allows for easy access to Joyce Middle School, Four Corners, Woburn Center and Routes 3 and 95, making commuting a breeze. The main level features an inviting living room, with wood-burning fireplace, that flows into an updated, eat-in kitchen with vaulted ceilings, quartz counters and stainless-steel appliances before leading to three bedrooms and a full bathroom. Head downstairs to the incredible finished basement that truly maximizes the space, from the workout room/office and laundry room to the dry bar, family room and half bath that ma

$775,000

3 beds1.5 baths1,980 sq ft

2 Locust Cir, Woburn, MA 01801

0.24 acre lot • Car-dependent

15 Tyler Rd, Lexington, MA 02420
15 Tyler Rd, Lexington, MA 02420
15 Tyler Rd, Lexington, MA 02420
ABOUT THIS HOME
Winchester, MA Homes for Sale
With its prime location, contemporary design, and an array of thoughtful upgrades, this property offers a lifestyle of comfort and sophistication. You'll be greeted by a beautifully landscaped front yard, setting the tone for what awaits inside. Step through the elegant front door, and you'll be immediately captivated by the bright and spacious interior with a stunning spiral staircase. The open-concept living spaces are flooded with natural light, with floor-to-ceiling windows. The gourmet kitchen is a chef's dream, boasting top-of-the-line stainless steel appliances, quartz countertops, and ample cabinet space. It seamlessly flows into the inviting family room with a magnificent fireplace

$4,600,000

6 beds6.5 baths7,739 sq ft

15 Tyler Rd, Lexington, MA 02420

0.69 acre lot • 3 garage spots • Car-dependent

NEW CONSTRUCTION

6 Stratton Dr #304, Woburn, MA 01801
6 Stratton Dr #304, Woburn, MA 01801
6 Stratton Dr #304, Woburn, MA 01801
ABOUT THIS HOME
Winchester, MA Homes for Sale
Welcome to the Jameson at Highland at Vale in Woburn! This beautifully designed home is flooded with natural light, creating a bright and inviting atmosphere. The chef-inspired kitchen boasts stainless steel appliances, a generous oversized island, and an abundance of cabinetry, perfect for culinary enthusiasts. The owner's suite is a serene retreat, featuring an extra-large walk-in closet and a spa-like bathroom for ultimate relaxation. Additionally, a versatile den with French doors offers a private space for work or leisure. With a perfect balance of comfort and style, this home is ideal for modern living!

$699,999

1 bed1 bath1,027 sq ft

6 Stratton Dr #304, Woburn, MA 01801

$397 HOA • Garage • Car-dependent

Property at 7 Crossman Rd, Woburn, MA 01801, 6 beds, 5 baths

$2,499,000

6 beds5 baths5,149 sq ft

7 Crossman Rd, Woburn, MA 01801

Property at 14 Church Ave Unit 2B, Woburn, MA 01801, 1 bed, 1 bath

$320,000

1 bed1 bath500 sq ft

14 Church Ave Unit 2B, Woburn, MA 01801

Property at 193 Park St, Stoneham, MA 02180, 3 beds, 2.5 baths

$679,900

3 beds2.5 baths2,499 sq ft

193 Park St, Stoneham, MA 02180

Property at 8 Grace Rd, Woburn, MA 01801, 4 beds, 2 baths

$999,950

4 beds2 baths1,918 sq ft

8 Grace Rd, Woburn, MA 01801

Property at 6 Mason Way #63, Woburn, MA 01801, 3 beds, 2.5 baths

$1,225,005

3 beds2.5 baths2,143 sq ft

6 Mason Way #63, Woburn, MA 01801

Property at 16 Winchester Dr, Lexington, MA 02420, 6 beds, 6.5 baths

$3,600,000

6 beds6.5 baths7,419 sq ft

16 Winchester Dr, Lexington, MA 02420

Property at 6 Stratton Dr #307, Woburn, MA 01801, 2 beds, 2 baths

$964,999

2 beds2 baths1,582 sq ft

6 Stratton Dr #307, Woburn, MA 01801

Property at 6 Stratton Dr #404, Woburn, MA 01801, 1 bed, 1 bath

$748,429

1 bed1 bath1,027 sq ft

6 Stratton Dr #404, Woburn, MA 01801

Property at 1 Mason Way #66, Woburn, MA 01801, 3 beds, 2.5 baths

$1,239,999

3 beds2.5 baths2,143 sq ft

1 Mason Way #66, Woburn, MA 01801

Property at 3 Archer Dr #3, Woburn, MA 01801, 4 beds, 3.5 baths

$1,349,900

4 beds3.5 baths3,450 sq ft

3 Archer Dr #3, Woburn, MA 01801

Property at 7 Prospect St, Woburn, MA 01801, 7 beds

$1,399,000

7 beds— baths6,700 sq ft

7 Prospect St, Woburn, MA 01801

Property at 6 Stratton Dr #310, Woburn, MA 01801, 2 beds, 2 baths

$849,999

2 beds2 baths1,425 sq ft

6 Stratton Dr #310, Woburn, MA 01801

Property at 14 Church Ave, Woburn, MA 01801, 5 beds, 4 baths

$1,498,000

5 beds4 baths3,276 sq ft

14 Church Ave, Woburn, MA 01801

Property at 5 Graystone Rd, Stoneham, MA 02180

$489,000

— beds— baths— sq ft

5 Graystone Rd, Stoneham, MA 02180

Average home prices near Winchester, MA

Cities

Neighborhoods
Zip Codes

West Side homes for sale
$3,898,000
Arlington Heights homes for sale
$1,399,900
West Medford homes for sale
$1,649,000
Arlington Center homes for sale
$1,490,000
Wedgemere homes for sale
$3,597,000
Montvale homes for sale
$1,294,950
Countryside homes for sale
$4,600,000
Winchester Highlands homes for sale
$1,074,999
Downtown Woburn homes for sale
$577,000
The Flats homes for sale
$3,450,000

Winchester, MA real estate trends

All Home Types trends in Winchester, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,542,500

+25.4% YoY | Jan 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jan 2025

Growth

% YoY

Winchester, MA

$1,542,500

+25.4%

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