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Homes For Sale in Winchester, MA

20,267
$143,317
01890

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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 Woburn, the neighboring city to the North.

Originally an agricultural community with upland farms on the western side of town near Lexington, the tiny village of 200 settlers evolved into a bustling mill town, with the advent of the Middlesex Canal and the Boston and Lowell Railroad



New Condos for Sale in Winchester, MA

New Listing

$925,000
Condo
Posted 1 day ago
7 Wainwright Road Winchester MA 01890 Condo for sale - MLS #71130660
3,919 sq. ft.

Lovely, end unit at the Ledges w/complete privacy on the cul de sac.This highly sought after well appointed "E" style offers a wonderful open floor plan, cathedral ceilings, wetbar, fire place family...

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View details for 7 Wainwright Road Winchester, MA 01890
New Listing

$729,000
Condo
Posted 3 days ago
10 Winchester Place Winchester MA 01890 Condo for sale - MLS #71129960
2,450 sq. ft.

Location, Location, Location! Fabulous single-level living; one-of-a-kind building in the center of town. Interior features include nine-foot ceilings, gleaming hardwood floors, handsome gas...

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View details for 10 Winchester Place Winchester, MA 01890
New Listing

$769,000
Condo
Posted 10 days ago
7 Wainwright Rd Winchester MA 01890 Condo for sale - MLS #71126802
2,613 sq. ft.

Live at the Ledges! This brightly lit "B" unit has been meticulously cared for by the original owner sits almost above the tree line. Kitchen with large eat in area, tile floor & recessed lighting....

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View details for 7 Wainwright Rd Winchester, MA 01890
New Listing

$479,000
Condo
Posted 13 days ago
55 Edward Drive Winchester MA 01890 Condo for sale - MLS #71126079
1,992 sq. ft.

Sought after 2+ bedroom townhome at Pepper Hill Estates. This spacious sun-filled unit has three floors of functional living space and features: updated gourmet granite eat-in kitchen, 1st floor...

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View details for 55 Edward Drive Winchester, MA 01890
New Listing

$735,000
Condo
Posted 14 days ago
90 Middlesex St Winchester MA 01890 Condo for sale - MLS #71125611
1,626 sq. ft.
8,276 sq. ft.

NEW CONSTRUCTION ~Custom 4 bedroom 2 1/2 bath home offering 4 generously sized bedrooms with hardwood floors and ample closet space.Master Suite with vaulted ceilings and privaste bath. First floor...

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View details for 90 Middlesex St Winchester, MA 01890

New Single Family Homes for Sale in Winchester, MA

New Listing

$299,900
Single Family
Posted a moment ago
40 White St Winchester MA 01890 Home for sale - MLS #71131224
1,595 sq. ft.
6,970 sq. ft.

Great location, nice size yard. Hardwoods. Nice size rooms. Some updates. Sold AS IS no warranties/guarantees/representations expressed or implied by broker or seller. All offers are contingent upon...

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View details for 40 White St Winchester, MA 01890
New Listing

$739,000
Single Family
Posted 1 day ago
33 Pierrepont Rd Winchester MA 01890 Home for sale - MLS #71130655
1,973 sq. ft.
0.26 acres

Lovingly maintained Gambrel, Dutch Colonial in East Hill neighborhood offers endless possibilities. Features include rich architectural details, spacious foyer, formal dining room with 2 built-in...

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View details for 33 Pierrepont Rd Winchester, MA 01890
New Listing

$694,900
Single Family
Posted 6 days ago
111 Wildwood St Winchester MA 01890 Home for sale - MLS #71129070
2,247 sq. ft.
7,405 sq. ft.

Renovated West Side colonial. Custom kitchen w/granite and tile, stainless appliances, new cabinets w/wine peninsula, wine fridge, opens to sunny breakfast rm with cathedral ceiling, skylight, sliders...

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View details for 111 Wildwood St Winchester, MA 01890
New Listing

$2,500,000
Single Family
Posted 7 days ago
19 Rangeley Road Winchester MA 01890 Home for sale - MLS #71128284
5,095 sq. ft.
0.77 acres

Rare opportunity to own a piece of Winchester's history. Formerly the carriage house for the David Skillings estate, this exquisite home sits on nearly an acre one block from town center, 7...

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View details for 19 Rangeley Road Winchester, MA 01890
New Listing

$499,000
Single Family
Posted 8 days ago
6 Spruce Street Winchester MA 01890 Home for sale - MLS #71128180
1,550 sq. ft.
7,841 sq. ft.

Everything is new again! Don't miss this delightfully bright and sunny Colonial that has been completely renovated with gleaming hardwood floors, a new eat-in kitchen, a convenient mudroom for all...

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View details for 6 Spruce Street Winchester, MA 01890

New Multi Family Homes for Sale Winchester, MA

$499,000
Multi-Family
Posted 1 month, 1 day ago
15-17 Dunham St Winchester MA 01890 House for sale - MLS #71117927
2,600 sq. ft.
8,712 sq. ft.

Located on a quiet cul de sac, this duplex home is within walking distance of the many shops and restaurants in Winchester. Both units have kitchen, living room, dining room, two bedrooms and full...

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View details for 15-17 Dunham St Winchester, MA 01890
$749,000
Multi-Family
Posted 1 month, 5 days ago
34-36 Mystic Avenue Winchester MA 01890 House for sale - MLS #71116252
3,233 sq. ft.
0.23 acres

Historic 1840 Philemon Symmes House originally built as an Italianate single family home has all the charm of yesteryear with high ceilings and custom molding in the lower unit and floor to ceiling...

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View details for 34-36 Mystic Avenue Winchester, MA 01890
$649,000
Multi-Family
Posted 1 month, 5 days ago
525-527 Washington St. Winchester MA 01890 House for sale - MLS #71116142
3,272 sq. ft.
0.24 acres
Price Reduced Login for details

Grand 15 room 2 family colonial with 3272 SF on corner lot in Muraco school district. First floor 2 bedroom 1 bath unit leased until 8/31/10 at $1650. Upper 5 bedroom 2 bath unit leased until 8/20/11...

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View details for 525-527 Washington St. Winchester, MA 01890
$639,000
Multi-Family
Posted 1 month, 8 days ago
529-531 Washington St Winchester MA 01890 House for sale - MLS #71114409
2,516 sq. ft.
0.24 acres
Price Reduced Login for details

Live in the #1 rated Muraco School district! Enjoy old world charm, original period details, with updated amenities.This two family home has hardwood floors throughout and recent renovations. The...

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View details for 529-531 Washington St Winchester, MA 01890
$519,000
Multi-Family
Posted 4 months, 1 day ago
59-61 Sheridan Cir Winchester MA 01890 House for sale - MLS #71075472
2,024 sq. ft.
9,583 sq. ft.
Price Reduced Login for details

Standard two family with two bedrooms on first floor, three bedrooms on second floor, large flat yard, stucco exterior, replacement windows. Could use some TLC but a solid house. Enclosed front...

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View details for 59-61 Sheridan Cir Winchester, MA 01890
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