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The average rent in Winchester, as of June 2026, is up 6.19% compared to last month and up 16.08% year-over-year.
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3d ago
Winchester Town Center townhouse for rent in Winchester
171 Swanton St #77, Winchester, MA 01890
In-unit laundry | Air conditioning | Garage parking
3 beds
2.5 baths
$4,550
The price shown reflects a 12-month lease. Fees may apply.House for rent
Available Jul 1
5d+ ago
Winchester Highlands condo for rent in Winchester
6365 Harvard St #2, Winchester, MA 01890
Garage parking | On-site laundry | Outdoor space
3 beds
2 baths
$3,400
The price shown reflects a 12-month lease. Fees may apply.Condo for rent
5d+ ago
Winchester Highlands house for rent in Winchester
41 Cross St, Winchester, MA 01890
Garage parking | On-site laundry | Outdoor space
4 beds
2 baths
$4,500
The price shown reflects a 12-month lease. Fees may apply.House for rent
5d+ ago
Winchester Town Center condo for rent in Winchester
On-site laundry | Hardwood floor | Outdoor space
Studio
1 bath
$1,800
The price shown reflects a 12-month lease. Fees may apply.Condo for rent
Available Aug 1
5d+ ago
Winchester Highlands apartment for rent in Winchester
2 beds
1 bath
$2,300
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Aug 1
5d+ ago
Winchester Town Center condo for rent in Winchester
Furnished | Air conditioning | On-site laundry
1 bed
1 bath
$2,250
The price shown reflects a 12-month lease. Fees may apply.Condo for rent
5d+ ago
Winchester Town Center townhouse for rent in Winchester
3 beds
1.5 baths
$4,995
The price shown reflects a 12-month lease. Fees may apply.House for rent
5d+ ago
Winchester Highlands apartment for rent in Winchester
1 bed
1 bath
$2,400
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
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4h ago
Verified
138 Pleasant St, Malden, MA 02148
In-unit laundry | Garage parking | Balcony
Studio–2 beds
1–2 baths
$2,636–$3,762
Price drop
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Apartment for rent
16h ago
Verified
2 Littles Brook Ct, Burlington, MA 01803
In-unit laundry | Air conditioning | Garage parking
1–2 beds
1–2 baths
$2,900–$4,130
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Apartment for rent
Swimming Pool
On-Site Laundry
Outdoor Space
Garage Parking
5d+ ago
Verified
3 beds
2 baths
$4,750
$4,275
Price drop
The price shown reflects a 12-month lease. Fees may apply.House for rent
Available Jun 1
1d ago
Verified
3 beds
1 bath
$4,200
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Aug 1
3d ago
Verified
82 Grant Ave, Medford, MA 02155
Hardwood floor | Dishwasher | Outdoor space
3 beds
1 bath
$3,000
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
3d ago
Verified
82 Grant Ave, Medford, MA 02155
Hardwood floor | Dishwasher | Outdoor space
2 beds
1 bath
$3,000
$2,800
Price drop
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
1d ago
Verified
306 Spring Street Ext, Medford, MA 02155
Hardwood floor | Dishwasher | Outdoor space
2 beds
1 bath
$3,000
$2,900
Price drop
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Aug 1
5d+ ago
Verified
32 Walnut St, Arlington, MA 02476
On-site laundry | Dishwasher
2 beds
1 bath
$2,950
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Jun 15
These rentals are 10%-30% cheaper than the local average price for similar rentals.
4h ago
Verified
595 Fellsway W, Medford, MA 02155
Furnished | Hardwood floor | Deck
2 beds
1 bath
$3,000
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Apr 22
5d+ ago
Verified
30 Mill St, Arlington, MA 02476
In-unit laundry | Air conditioning | Garage parking
1 bed
1 bath
$2,381
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Mar 5
5d+ ago
Verified
92 Sylvia St, Arlington, MA 02476
On-site laundry | Hardwood floor | Dishwasher
3 beds
1 bath
$3,000
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Apr 5
1d ago
Verified
21 Jerome St, Medford, MA 02155
On-site laundry | Deck | Dishwasher
3 beds
1.5 baths
$3,900
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
1d ago
Verified
134 Summer St #44, Malden, MA 02148
Air conditioning | On-site laundry | Hardwood floor
2 beds
2 baths
$2,850
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
1d ago
Verified
170 Maple St #209, Malden, MA 02148
On-site laundry
1 bed
1 bath
$2,300
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
1d ago
Verified
134 Summer St #32, Malden, MA 02148
Air conditioning | On-site laundry | Hardwood floor
1 bed
1 bath
$2,300
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
5d+ ago
Verified
30 Mill St, Arlington, MA 02476
In-unit laundry | Air conditioning | Garage parking
2 beds
2 baths
$3,526
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Mar 5
5d+ ago
Verified
3 beds
1 bath
$3,500
The price shown reflects a 12-month lease. Fees may apply.Apartment for rent
Available Sep 1
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Winchester offers a blend of suburban tranquility and easy access to urban amenities, which residents appreciate. Many enjoy the picturesque neighborhoods and well-maintained parks, making it ideal for families. The local schools receive high marks, adding to the appeal for those with children. However, some residents express concerns about the high cost of living and limited entertainment options, suggesting that when it comes to dining and nightlife, the options can feel somewhat lacking. Overall, life in Winchester is characterized by its residential feel and accessibility to Boston.
The average rent for a 1-bedroom apartment in Winchester, MA is $2,013, while a 2-bedroom apartment averages $2,963.
It is generally advisable to start your search a few months before your planned move, especially in sought-after areas like Winchester Town Center.
Winchester Town Center leads the rental market, representing 82% of available inventory and offering strong community connections with high walk scores and frequent transit options. Winchester Highlands also provides excellent social living opportunities with well-developed street infrastructure and diverse age distributions that create natural gathering spaces for residents.
Winchester Town Center offers budget-friendly options around $2,080 per month, running 4% below the city median. This neighborhood provides the most rental inventory while maintaining access to community-focused amenities and sustainable living features.
Yes, there are pet-friendly apartments in Winchester, with 18.72% of listings being pet-friendly.
Winchester rentals rarely include utilities, with less than 1% of total listings offering this feature. Studios occasionally include utilities at around 0.3% of available units, while one-bedroom, two-bedroom, and three-bedroom apartments virtually never include utilities as part of the rent.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
| 🔑Available apartment rentals | 25 |
|---|---|
| 💰Best rent deal | 200 Swanton St #T34 |
| ✨Popular amenities | , , |
| 🧦In-unit laundry | |
| 🏠With photos |