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Winchester, MA

4 Multi Families

$799,000 - $1,250,000

41 Condos

$279,000 - $1,600,000

154 Single Families

$509,000 - $4,499,000


Homes For Sale in Winchester, MA

199 homes for sale

$569,900
$740,683
$1,222,500
$1,447,600
$1,062,000
$1,043,250

Conveniently located just eight miles northwest of Boston, the Town of Winchester has developed from its seventeenth century colonial village beginnings into a thriving residential community noted for its fine public school system, beautiful homes and easy access to Boston.

Settled in the early 1600's by citizens from Charlestown, the village was first known as Waterfield and became part of...

Learn more about Winchester

01890

Local Info

20,267
$143,317.00
More Local Info

Market Info

$1,163,080
$14,597
More Market Info

Recent Sales

More Recent Sales

New Single Family Homes for Sale in Winchester, MA

New Listing
New Listing

$999,000
Single Family
Posted 1 day ago
2 Ainsworth Rd, Winchester, MA 01890 Home For Sale - MLS #72535201
2,896 sq. ft.
0.33 acres

Sunny, updated 3 bed 2.5 bath cape located on a cul-de-sac near Fells Reservation in Winchester Highlands. First floor boasts open chef?s kitchen, dining area with built-ins, and family room with...

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New Listing
New Listing

$749,900
Single Family
Posted 1 day ago
8 Garfield Ave, Winchester, MA 01890 Home For Sale - MLS #72535169
1,306 sq. ft.
6,534 sq. ft.

Take a step inside this charming three bedroom Colonial with abundant light and Nest-controlled central air, perfectly suited for a couple or small family. Walk into the beautiful living room with...

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New Listing
New Listing

$799,000
Single Family
Posted 2 days ago
3 Orient St, Winchester, MA 01890 Home For Sale - MLS #72534589
1,708 sq. ft.
7,841 sq. ft.

The perfect Arts n Crafts bungalow circa 1925, 3 Orient St offers the option of one level living or a spacious 2nd floor Master bedroom. This carefully maintained home features an updated kitchen, 1st...

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New Listing
New Listing

$1,100,000
Single Family
Posted 5 days ago
26 Grove Street, Winchester, MA 01890 Home For Sale - MLS #72533510
1,776 sq. ft.
0.46 acres

You will be charmed by this historic light-filled home with an expansive yard. Built in 1835, this four bedroom home has been impeccably maintained---inside and out! With shiny, hardwood floors...

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New Listing
New Listing

$1,199,000
Single Family
Posted 5 days ago
50 Myrtle Terrace, Winchester, MA 01890 Home For Sale - MLS #72533412
3,133 sq. ft.
0.27 acres

Best of both worlds~Close to Winchester Center and The Fells! Beautifully renovated 5 bedroom 3 bath home nestled in great Lincoln School neighborhood, with a dreamy oversized backyard! Lovely...

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New Condos for Sale in Winchester, MA

New Listing
New Listing

$1,299,000
Condo
Posted a moment ago
22 Gershon Way Unit 22, Winchester, MA 01890 Condo For Sale - MLS #72535655
2,980 sq. ft.

WINCHESTER'S 1ST 55+ LUXURY COMMUNITY!!! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury...

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New Listing
New Listing

$618,000
Condo
Posted 5 days ago
666 Main Unit 4410, Winchester, MA 01890 Condo For Sale - MLS #72533470
1,170 sq. ft.

CLICK THE "V" ON TOP RIGHT FOR 3D TOUR! Welcome to Wedgewood Place, on Wedge Pond in the heart of Winchester Center! Talk about LOCATION...In 2017, Boston Magazine chose Winchester as one of the "Best...

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New Listing
New Listing

$665,000
Condo
Posted 6 days ago
3 Myrtle Street Unit 2, Winchester, MA 01890 Condo For Sale - MLS #72532754
2,177 sq. ft.

Most desireable neighborhood located in the heart of Winchester center - walk to shops, restaurants, tennis, beach, all schools, and commuter rail to Boston. Directly across from Chefalo Park and the...

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New Listing
New Listing

$1,020,000
Condo
Posted 6 days ago
7 Wainwright Rd Unit 114, Winchester, MA 01890 Condo For Sale - MLS #72532221
3,000 sq. ft.

Light-filled "A" style Townhome with custom oak finishes and sought after first floor master bedroom at The Ledges! From the moment you step through the door, you'll notice the beautiful oak flooring...

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New Listing
New Listing

$389,000
Condo
Posted 14 days ago
200 Swanton Unit 203, Winchester, MA 01890 Condo For Sale - MLS #72529104
822 sq. ft.

A great opportunity to own in beautiful Winchester, moments away from Winchester Center, restaurants, shops, parks, and much more awaits. Enjoy this generously sized two bedroom unit at the Parkview...

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New Multi Family Homes for Sale Winchester, MA

New Listing
New Listing

$799,000
Multi-Family
Posted a moment ago
5-7 Sheridan Cir, Winchester, MA 01890 House For Sale - MLS #72536023
3,364 sq. ft.
7,405 sq. ft.

RARE OPPORTUNITY to own this side by side two-family home in Winchester!!! 2 family home with 3 Level living. 3-4 bedrooms and 2 full baths on each side. with potential third floor expansion or condo...

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$1,199,000
Multi-Family
Posted 2 months, 10 days ago
143-145 Cambridge St, Winchester, MA 01890 House For Sale - MLS #72496530
3,000 sq. ft.
0.29 acres

Legal 2 Family with 3 car detached garage. Located near the Flats of Winchester is this stately legal 2 family home with a detached 3 car garage and parking for several more vehicles. Built in 1860...

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$925,000
Multi-Family
Posted 3 months, 8 days ago
4-6 Westley Street, Winchester, MA 01890 House For Sale - MLS #72479478
2,856 sq. ft.
4,356 sq. ft.

Excellent opportunity to own an investment property in convenient Winchester location. This well-maintained two-family property, in the Lincoln Elementary School district, is just .5 miles from...

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$1,250,000
Multi-Family
Posted 5 months, 2 days ago
8-10 Winter St, Winchester, MA 01890 House For Sale - MLS #72453632
2,484 sq. ft.
9,583 sq. ft.

OUTSTANDING DUPLEX IN WINCHESTER!!! Two-Family DUPLEX Style Home on EXTRA LARGE LOT with TWO driveways.THIS HOME HAS BEEN COMPLETELY RENOVATED , EVERYTHING IS BRAND NEW ! Close to Winchester's FINEST...

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Winchester Services

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Newest Listings