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253 Apartments for rent in Winchester, MA

Read Guide >
Last updated October 16 at 7:28am UTC
40 Church
Winchester, MA
Updated October 11 at 7:40am UTC
4 Bedrooms
40 Church
Winchester, MA
Updated October 10 at 10:34am UTC
3 Bedrooms
7 Valley Rd
Winchester Highlands
Winchester, MA
Updated October 3 at 10:23am UTC
4 Bedrooms
32 Surrey Road
Winchester, MA
Updated September 25 at 4:28pm UTC
5 Bedrooms
Results within 1 miles of Winchester, MA
1 Watermill Place
Arlington, MA
Updated October 12 at 7:12am UTC
2 Bedrooms
49 Summer St #2b
Arlington, MA
Updated October 11 at 7:32am UTC
2 Bedrooms
8 Common St
Colonial Park
Stoneham, MA
Updated October 9 at 11:06pm UTC
2 Bedrooms
24 Century Street
West Medford
Medford, MA
Updated September 24 at 4:58am UTC
2 Bedrooms
22 Wheelwright Road 2
West Medford
Medford, MA
Updated September 19 at 4:16pm UTC
3 Bedrooms
127 Lowell St
East Lexington
Lexington, MA
Updated August 11 at 6:51pm UTC
5 Bedrooms
Results within 5 miles of Winchester, MA
Hanover Cambridge Park
80 Cambridgepark Drive
Cambridge, MA
Updated October 16 at 7:25am UTC
1 Bedroom
2 Bedrooms
City Guide
Moving to Winchester

Demand for rental homes in Winchester is high, so it is important to plan in advance if you are interested in moving to the city. The price of homes in Winchester didn't fall much during the national real estate crisis of 2008, and median home prices has risen gradually since then as well. Because demand for rental apartments and rental condos is so high, it can be hard to find furnished apartments in the city without at least a month or two of advance scouting. If you do decide to scout places to live in Winchester, be sure to learn about the different neighborhoods ahead of time in order to find the place best suited to your situation.

Neighborhoods in Winchester

The city of Winchester is broken into five major neighborhoods. While all the neighborhoods have an abundance of trees and natural beauty, one size does not fit all.

Winchester Highlands: This is the easternmost neighborhood in Winchester and also the most spread out. While there are numerous scenic vistas of trees and lakes in Winchester Highlands, it also takes longer to reach major highways and roads into Boston.

Washington Street and Cross Street: This is the northernmost neighborhood in the city, and is the first place incoming residents should look if they want large single-family homes that are four bedrooms and above.

Downtown Winchester: Downtown Winchester is home of many of the oldest and most historic buildings in Winchester. For residents looking for 1 bedroom apartments for rent, this is the first place to look.

Cambridge Street and High Street: Located at the heart of the city, this neighborhood is where you'll find some of the most popular restaurants in Winchester, such as A Tavola and Lucia Ristorante.

Church Street and Fletcher Street: This is the westernmost part of the city, as well as the area most often in high demand. Many of Winchester's established families live in this part of town, and the homes found here are often true works of art.

Things to do in Winchester

You can always sleep or brush up on your bird watching, but with the city of Boston just eight miles away, many residents of this bedroom community tend to simply commute to the city for their entertainment. However, Winchester is known for their abundance of woodland areas, as well as the water park known as Splash Park. Get wet and wild at this fun and exciting recreation spot. During the summers, of course, because the winters can be just a little frosty.