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!

And, for your convenience, feel free to register for a free account to receive email alerts whenever new Winchester listings come on the market that match your specific criteria.

Winchester May 31, 2023
29
Listed
30
Avg. DOM
$540.76
Avg. $ / Sq.Ft.
$1,699,000
Med. List Price
29 Properties
Page 1 of 2
Open 6/1
14 Bonad Rd Winchester,  MA 01890
3
Beds
2F11/2
Baths
2,604
Sq.Ft.
1942
Year Built
1
Day on Site
73115173
MLS
Tasteful updates & thoughtful design shine through in this meticulously cared for Cape-Cod style home. Step into the bright and airy dining room adorned w/ elegant French doors that flow seamlessly...
Open 6/2
6 Ivy Cir Winchester,  MA 01890
3
Beds
2F11/2
Baths
2,307
Sq.Ft.
1966
Year Built
1
Day on Site
73118070
MLS
First time on the market; one owner for 57 years. Enjoy all Winchester has to offer in this Colonial at the end of a cul-de-sac with a near center location. Hardwood floors in the living room,...
Open 6/2
19 West Chardon Rd Winchester,  MA 01890
4
Beds
1F11/2
Baths
1,922
Sq.Ft.
1957
Year Built
2
Days on Site
73117532
MLS
Preparation meets opportunity! Contemporary multi-level with wonderful space & functionality in sought-after neighborhood. This home offers lifestyle advantages on 3 floors ~ whether gathering w/...
3
Beds
1
Baths
1,156
Sq.Ft.
1915
Year Built
5
Days on Site
73116698
MLS
Looking for affordable real estate in desirable Winchester? Contractors and savvy buyers take notice. Built in 1915, this 3 bedroom, 1 bathroom, 1156 sq.ft. Single Family property at 30 Florence...
Open 6/3
12 James St Winchester,  MA 01890
3
Beds
1F11/2
Baths
1,548
Sq.Ft.
1950
Year Built
8
Days on Site
73115607
MLS
Great opportunity to own in Winchester. Lovingly maintained ranch style home in Vinson-Owen district features hardwood floors throughout, a sunny living room with fireplace and large picture window,...
4
Beds
3F11/2
Baths
3,380
Sq.Ft.
1927
Year Built
8
Days on Site
73116002
MLS
Extensive renovation and addition of classic center entrance colonial. The first floor offers a kitchen with island, gas fireplaced family room with sliders leading to a new deck, original fireplace...
4
Beds
3F21/2
Baths
4,750
Sq.Ft.
2007
Year Built
10
Days on Site
73114972
MLS
Location is key for this stunning Colonial home situated on a quiet street. Exquisite craftsmanship, opulent finishes, & meticulous upgrades define this must-see property. The open concept kitchen,...
Open 6/3
11 Main St Winchester,  MA 01890
3
Beds
2
Baths
1,840
Sq.Ft.
1957
Year Built
13
Days on Site
73114160
MLS
This stunningly updated ranch features new appliances, new granite countertops and backsplash, gleaming hardwood floors throughout the home, and beautifully updated bathrooms. Large windows allow for...
Open 6/1
22 Fletcher St Winchester,  MA 01890
3
Beds
2F11/2
Baths
2,343
Sq.Ft.
1901
Year Built
14
Days on Site
73113387
MLS
Great single-family alternative in sought after Winchester Flats. This beautiful previously gut-renovated Townhome lives like a single-family with huge backyard and patio. Close to town center....
$1,799,000
Neighborhood: West side
5
Beds
2F11/2
Baths
4,532
Sq.Ft.
1964
Year Built
14
Days on Site
73113874
MLS
Inviting family home located in a picture perfect neighborhood, situated among beautifully maintained, high-end homes. This 5 Bedroom 2.5 bath colonial will meet your every need~ over 4500 sf of...
4
Beds
2F11/2
Baths
3,003
Sq.Ft.
1906
Year Built
15
Days on Site
73112587
MLS
Welcome to life on Winter Pond! Exquisitely updated four bedroom Colonial with breathtaking views and direct pond access. Kayaking, ice skating, & lovely swans! Expansive living room with central...
3
Beds
2
Baths
1,743
Sq.Ft.
1909
Year Built
15
Days on Site
73113100
MLS
Colonial farmhouse on private 4,318 sqft lot at the end of a private cul-de-sac. Needs some cosmetics but most major items done. Recent renovations from 2010 include new kitchen and 1st floor...
8
Beds
5F21/2
Baths
6,484
Sq.Ft.
1900
Year Built
16
Days on Site
73112247
MLS
Introducing 319 Main Street...a remarkable colonial showcasing exquisite craftsmanship & details throughout! Situated in a prime location, this stately home offers a grand front brick porch providing...
4
Beds
4F11/2
Baths
2,465
Sq.Ft.
1930
Year Built
16
Days on Site
73112321
MLS
Great Single Family Alternative! Classic architectural details meet modern farmhouse in this completely gut renovated 4-bed, 4.5 bath townhome with 2,465sf of interior space over 4 levels. An...
4
Beds
4F11/2
Baths
2,275
Sq.Ft.
1930
Year Built
16
Days on Site
73112324
MLS
Great Single Family Alternative! Classic architectural details meet modern farmhouse in this completely gut renovated 4-bed, 4.5 bath townhome with 2,275sf of interior space over 4 levels. An...
$2,799,000
Neighborhood: cul- de- sac off south border/ near town
5
Beds
5
Baths
5,000
Sq.Ft.
2023
Year Built
29
Days on Site
73107072
MLS
NEW CONSTRUCTION!! Must see this gorgeous 5 bedroom home with thoughtful design & high end finishes! This home is spacious and inviting, offering a grand open floor plan ideal for entertaining &...