Winchester MA Homes & Real Estate

Included below are homes for sale and real estate in Winchester, MA.

If you would like more information on any of these Winchester real estate listings, just click on a property to access the full details. From there, you can request more information or schedule a tour. And we'd be happy to provide you with disclosures, past sales history, dates and prices of properties which have recently sold nearby, and more, so just let us know how we can help!

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Winchester October 2, 2022
27
Listed
45
Avg. DOM
$525.46
Avg. $ / Sq.Ft.
$1,699,000
Med. List Price
27 Properties
Page 1 of 2
Open 10/2
49 Myrtle Terrace Winchester, MA 01890
5
Beds
3F11/2
Baths
2,788
Sq.Ft.
1921
Year Built
4
Days on Site
73042371
MLS
Autumn always brings something special and here she is! This stunning Highlands Victorian perched high on the Terrace, is super close to the Fells, town center, highway, and schools. Renovated to the...
Open 10/2
16 Bellevue Avenue Winchester, MA 01890
3
Beds
1F11/2
Baths
1,791
Sq.Ft.
1957
Year Built
5
Days on Site
73042012
MLS
Welcome to this charming multi-level home nestled on a generous corner lot, in a desirable Winchester neighborhood. The newly remodeled contemporary kitchen showcases white cabinets, granite...
Open 10/2
9 Valley Road Winchester, MA 01890
3
Beds
2
Baths
1,941
Sq.Ft.
1950
Year Built
6
Days on Site
73041514
MLS
Mid-Century gem with period details just steps from "The Fells Reservation". This 3 Bedroom, 2 full bath expanded Cape house is renovated to perfection with designer touches through-out. Enjoy a...
4
Beds
2F11/2
Baths
2,763
Sq.Ft.
1920
Year Built
7
Days on Site
73040884
MLS
Townhouse, also listed as MLS 73040882. One of two units. Charm and character, blended with modern sophistication. This home lives like a single family and makes you feel a bit like you're in Back...
Open 10/2
5 Ainsworth Winchester, MA 01890
$1,799,999
Neighborhood: Winchester Highlands
4
Beds
2F11/2
Baths
3,288
Sq.Ft.
1984
Year Built
7
Days on Site
73041183
MLS
This special Winchester Highlands property boasts an EPIC, CUSTOM-BUILT, 2-STORY CARRIAGE HOUSE - A FINELY CRAFTED, ONE-OF-A-KIND structure ideal for a workshop, entertainment or artist studio....
$939,000
Neighborhood: Winter pond area
3
Beds
2F11/2
Baths
1,664
Sq.Ft.
1927
Year Built
12
Days on Site
73039540
MLS
A must see 3 bed 2.5 ba home situated on a 20,000 sf lot across from Little Winter pond with an amazing yard & close proximity to town! This adorable updated brick Cape features a front to back...
Open 10/2
4-4A Rangeley Rd Winchester, MA 01890
5
Beds
3F11/2
Baths
3,647
Sq.Ft.
1876
Year Built
14
Days on Site
73038416
MLS
A rare opportunity to own a remarkable brick 2 family home on a large lot in a top location within Winchester Center. Could be a prestigious single family home with au pair or in law suite. A sun...
5
Beds
3F11/2
Baths
3,769
Sq.Ft.
1948
Year Built
18
Days on Site
73037552
MLS
Welcome to 39 Everett Avenue, a classic mid-century modern home situated on a 25,000+ sf lot in the heart of Winchester's coveted Everett Ave. neighborhood. Embrace the abundance of natural light...
4
Beds
2F11/2
Baths
2,565
Sq.Ft.
1963
Year Built
25
Days on Site
73034074
MLS
Welcome to this well-maintained Colonial situated on a dead end street located close to the Tri-Community Bike Path / directly across from Muraco elementary, Leonard Field Rec. area, playground &...
6
Beds
3F11/2
Baths
5,265
Sq.Ft.
1890
Year Built
26
Days on Site
73033237
MLS
Unparalleled privacy ~ a tranquil retreat & a pristine neighborhood right at your fingertips! Imagine bedrooms w/window seats & a private deck connected to your primary suite all perched behind a...
$2,849,000
Neighborhood: Downtown location
6
Beds
4F11/2
Baths
6,100
Sq.Ft.
1908
Year Built
26
Days on Site
73033839
MLS
Majestic 6 bed 4.5 bath Victorian home w/ stunning rear addition located on one of Winchester's most highly desired streets close to the center, schools & train to Boston! A gorgeous new wrap around...
Open 10/2
107 Sylvester Avenue Winchester, MA 01890
3
Beds
2
Baths
1,979
Sq.Ft.
1928
Year Built
27
Days on Site
73032684
MLS
Get ready to F-A-L-L in love! Summer may be over but the property we are about to introduce to you is HOT! Boasting 3 bedrooms and 2 full bathrooms and a multitude of updates, this home may be the...
6
Beds
5F21/2
Baths
5,268
Sq.Ft.
2002
Year Built
27
Days on Site
73032962
MLS
Stunning custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18 high coffered ceilings...
4
Beds
2F11/2
Baths
3,293
Sq.Ft.
2015
Year Built
39
Days on Site
73029533
MLS
Amazing home built in 2015 on a quiet dead-end street, this 4 bedroom, 2.5 bathroom home has over 3293 sf of living area, and an attached 2 car garage. Elegant foyer with high ceilings leads to...
Open 10/2
2 Reservoir Street Winchester, MA 01890
5
Beds
3F11/2
Baths
4,267
Sq.Ft.
2022
Year Built
45
Days on Site
73027354
MLS
Elegant & spacious new construction in one of Winchester's coveted neighborhoods situated steps from the Middlesex Fells Reservation, minutes from downtown Boston & within close proximity to town...
Open 10/2
83 Main St Winchester, MA 01890
3
Beds
2
Baths
2,152
Sq.Ft.
1941
Year Built
48
Days on Site
73025920
MLS
Charming Cape located in desirable Winchester! With a little imagination and a few updates, this will be the house of your dreams! Spacious first floor layout w/ a living room featuring wood floors...