300 Apartments for rent in Winchester, MA

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Last updated November 23 at 12:27pm UTC
34 Charles
Winchester Highlands
Winchester, MA
Updated November 4 at 2:19am UTC
3 Bedrooms
$2,075
58 Charles Rd
Winchester Highlands
Winchester, MA
Updated November 11 at 9:25am UTC
3 Bedrooms
$2,600
200 Swanton St
Winchester Highlands
Winchester, MA
Updated November 3 at 2:46am UTC
2 Bedrooms
$1,850
7-9 Myrtle Street
Wedgemere
Winchester, MA
Updated September 28 at 2:31am UTC
3 Bedrooms
$3,200
1 Everett Ave
Wedgemere
Winchester, MA
Updated November 8 at 5:40pm UTC
5 Bedrooms
$7,500
11 Highland View Ave
Winchester Highlands
Winchester, MA
Updated November 5 at 9:20am UTC
3 Bedrooms
$3,600
Results within 1 miles of Winchester, MA
21 Mystic River
West Medford
Medford, MA
Updated November 17 at 10:12am UTC
3 Bedrooms
$2,600
53 Forest St
Brattle
Arlington, MA
Updated November 23 at 9:37am UTC
2 Bedrooms
$1,900
52 Bower St
West Medford
Medford, MA
Updated November 17 at 2:10am UTC
2 Bedrooms
$2,100
Results within 5 miles of Winchester, MA
35 Prospect St. Unit 305
Downtown Woburn
Woburn, MA
Updated November 12 at 10:32am UTC
1 Bedroom
$1,425
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City Guide
Winchester
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.