Massachusetts is rich in American history and renowned for its beautiful cities and breathtaking natural landscapes. Visit historical sites such as the Freedom Trail and USS Constitution Museum to experience the birthplace of America. In addition, it's the home to world-class universities such as Harvard University, Massachusetts Institute of Technology (MIT), and Boston College, adding to the state's innovation and education. Massachusetts also has a strong job market and a thriving economy.

For sports fans, Massachusetts is home to the New England Patriots (NFL), Boston Bruins (NFL), Boston Red Sox (MLB), Boston Celtics (NBA), and iconic venues such as Fenway Park and Gillette Stadium. In addition, the state offers a diverse range of outdoor experiences for those seeking adventure, from whale watching on the Cape Cod coast to hiking in the scenic Berkshire Mountains. See famous attractions like the Salem Witch Trials Memorial, the New England Aquarium, and the charming Martha's Vineyard.

With its warm and welcoming atmosphere, rich historical heritage, and endless opportunities, embrace the Bay State and discover why Massachusetts is the ideal place to call home.

Rental Market Trends

Winchester, MA

As of May 2026, Winchester's rental market is competitive, with strong renter demand causing quick leasing times for well-priced units. Winchester's average rent is 5.9% ($161) lower than the Massachusetts average of $2,734 and 43.8% ($784) higher than the U.S. average of $1,789.

Average Rent

$2,573

Monthly ChangeMonth Over Month Change

1.3% ($34)

Yearly ChangeYear Over Year Change

32.2% ($1223)

Avg. Days on MarketAverage Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$2,087	5.5% ($108)	23.1% ($626)
2 Beds	$3,537	38.8% ($989)	24.5% ($1148)
3 Beds	$4,523	35.4% ($1183)	17.1% ($935)

Nearby Cities	Average Rent	Avg. Rent vs. WinchesterAverage Rent vs. Winchester	Avg. Days on MarketAverage Days on Market
Woburn	$2,774	7.8% ($201)	22 days
Arlington	$2,554	0.7% ($19)	58 days
Medford	$2,631	2.3% ($58)	27 days
Stoneham	$3,079	19.7% ($506)	24 days
Lexington	$3,438	33.6% ($865)	25 days

Rental market trends are calculated using listing data from RentalSource.

Frequently Asked Questions

Winchester Rental Market FAQs

Explore rental prices, market trends, and availability in Winchester, MA.

What is the average rent in Winchester, MA?

The average rent in Winchester, MA is $2,573 per month.

What is the rental price range for homes in Winchester, MA?

Homes in Winchester typically rent for between $1,461 and $5,880 per month, with an average of $2,573 per month.

What is the average rent for different bedroom sizes in Winchester, MA?

In Winchester, the average rent for a 1-bedroom home is $2,087 per month, for a 2-bedroom home, $3,537 per month, and a 3-bedroom home is $4,523 per month.

How do rent prices in Winchester, MA compare with the national average?

The average rent in Winchester is 43.8% ($784) higher than the national average of $1,789 per month.

How have rent prices in Winchester, MA changed recently?

The average rent in Winchester has decreased by 1.3% ($34) in the last month and decreased by 32.2% ($1,223) over the past year.

How competitive is the rental market in Winchester, MA?

The rental market in Winchester, MA, is currently competitive, with strong renter demand causing quick leasing times for well-priced units.

How long do rentals stay on the market in Winchester, MA?

In Winchester, MA, the average rental stays on the market for approximately 27 days. While most properties are rented within this timeframe, factors like seasonality, demand, and property type can affect how quickly a rental leases.

How many rental properties are available in Winchester, MA?

There are currently 7 rental properties available in Winchester, MA.

Can I afford to rent a home in Winchester, MA?

Based on the current averages, a household would need an annual income of $141,480 to comfortably afford a 2-bedroom home in Winchester.