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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 Winchester Condos for Sale in Winchester, MA

7 Conant Road, Unit 22
Winchester, MA 01890
New Listing

$385,000
Condo
Posted a moment ago
7 Conant Road Winchester MA 01890 Condo for sale - MLS #71044627
1,236 sq. ft.

Beautiful 2 BR 2BA unit in " The Willows" .Unit has many desirable features: sunfilled, spacious open floor plan, gas fireplace in living rm, recently installed bamboo flooring and painted walls,C/A,...

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View details for 7 Conant Road Winchester, MA 01890
26 Vine St, Unit 26
Winchester, MA 01890
New Listing

$665,000
Condo
Posted 4 days ago
26 Vine St Winchester MA 01890 Condo for sale - MLS #71042467
2,332 sq. ft.

Great opportunity to own waterfront property with spectacular views of Wedge Pond and be in the heart of Winchester Center.Walk to shopping and trains.This renovated Victorian Townhouse has all the...

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View details for 26 Vine St Winchester, MA 01890
115 Washington St, Unit 3A
Winchester, MA 01890
New Listing

$439,000
Condo
Posted 6 days ago
115 Washington St Winchester MA 01890 Condo for sale - MLS #71041431
1,350 sq. ft.

Natural sun light flows into this penthouse unit! Walk to train, center of town, parks and public transportation. Two floors of open concept at its finest. The unit is in impeccable condition with...

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View details for 115 Washington St Winchester, MA 01890
64 Highland Avenue, Unit 16
Winchester, MA 01890
New Listing

$249,000
Condo
Posted 6 days ago
64 Highland Avenue Winchester MA 01890 Condo for sale - MLS #71041147
758 sq. ft.

Fabulous Waterfield Square converted schoolhouse Spacious one bedroom unit in meticulous condition.all updated and ready for occupancy Located across from Fells Reservation and walking trails. ...

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View details for 64 Highland Avenue Winchester, MA 01890
29 Vine St, Unit 05
Winchester, MA 01890
New Listing

$329,000
Condo
Posted 9 days ago
29 Vine St Winchester MA 01890 Condo for sale - MLS #71039049
1,338 sq. ft.

Walking distance to town center and commuter rail, this bright, and spacious two bedroom, two-balcony PENTHOUSE UNIT is exactly what you are looking for. Features a huge living room with fireplace and...

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View details for 29 Vine St Winchester, MA 01890

New Single Family Homes for Sale in Winchester, MA

81 Lawson Road
Winchester, MA 01890
New Listing

$2,295,000
Single Family
Posted a moment ago
81 Lawson Road Winchester MA 01890 Home for sale - MLS #71044636
6,000 sq. ft.
0.31 acres

Designed to be a masterpiece in home building, this quintessential New England styled Colonial with shingle & stone facade rests in sought after Lawson/Ledgewood area. Bright and inviting large open...

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View details for 81 Lawson Road Winchester, MA 01890
22 South Gateway
Winchester, MA 01890
New Listing

$1,249,000
Single Family
Posted a moment ago
22 South Gateway Winchester MA 01890 Home for sale - MLS #71044573
4,685 sq. ft.
0.37 acres

This is a home that just enthralls...it's gorgeous. Wide plank Brazilian cherry highlights the interior & spectacular stone work in the kitchens & baths showcase the workmanship. Sun-drenched &...

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View details for 22 South Gateway Winchester, MA 01890
16 Webster St
Winchester, MA 01890
New Listing

$1,475,000
Single Family
Posted 1 day ago
16 Webster St Winchester MA 01890 Home for sale - MLS #71043887
4,400 sq. ft.
0.34 acres

A truly unique home! Built in 1999 by an accomplished local builder for his family, this property offers the charm and warmth of an older home with all the amenities of today. Pristine parquet floors,...

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View details for 16 Webster St Winchester, MA 01890
16 Brooks Street
Winchester, MA 01890
New Listing

$1,269,000
Single Family
Posted 1 day ago
16 Brooks Street Winchester MA 01890 Home for sale - MLS #71043881
3,491 sq. ft.
0.24 acres

The Denneson House Turn of the century1898 stately Queen Anne colonial located in one of Winchester's finest neighborhoods. Such curbside appeal with inviting front porch Double parlors and...

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View details for 16 Brooks Street Winchester, MA 01890
18 Lloyd Street
Winchester, MA 01890
New Listing

$749,900
Single Family
Posted 1 day ago
18 Lloyd Street Winchester MA 01890 Home for sale - MLS #71043868
1,909 sq. ft.
5,227 sq. ft.

Glorious colonial tastefully updated complimented by many original details. Elegant hardwood foyer, pocket doors, open concept living featuring LR/DR combination. Recently remodeled kitchen with...

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View details for 18 Lloyd Street Winchester, MA 01890

New Multi Family Homes for Sale Winchester, MA

5-7 Sheridan Circle
Winchester, MA 01890
New Listing

$599,900
Multi-Family
Posted 9 days ago
5-7 Sheridan Circle Winchester MA 01890 House for sale - MLS #71038986
3,284 sq. ft.
7,405 sq. ft.

Property is available for sale in its entirety as a duplex or #5 is available separately as a condominium. Tenant pays $2050 plus utilities. Newer roof and windows - many upgrades.


View details for 5-7 Sheridan Circle Winchester, MA 01890
12 Norwood Street
Winchester, MA 01890
$1,249,000
Multi-Family
Posted 6 months, 1 day ago
12 Norwood Street Winchester MA 01890 House for sale - MLS #70972684
3,489 sq. ft.
0.24 acres
Price Reduced Login for details

Timeless, Victorian 2 family home in the coveted Flats neighborhood close to Ambrose School, downtown & trains. Magnificent details include original woodwork, moldings, pocket doors, prof decor,...

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View details for 12 Norwood Street Winchester, MA 01890
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