13 Center St
WoburnMA01801
Cheap Homes for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,000 (16 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St, Unit 240
200 Swanton St
WinchesterMA01890
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
74 Beach St
WoburnMA01801
200 Swanton St, Unit 708
200 Swanton St
WinchesterMA01890
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
200 Swanton St
WinchesterMA01890
35 Prospect St, Unit 311
35 Prospect St
WoburnMA01801
33 Montvale Ave
WoburnMA01801
200 Swanton St, Unit 313
200 Swanton St
WinchesterMA01890
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
39 Montvale Ave
WoburnMA01801
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$2,2001 Bedroom Apartments Available Now
78 Mill St, Unit 10
78 Mill StWoburn, MA 01801
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$2,2001 Bedroom Apartments Available Nov 1
70 Mill St, Unit 6
70 Mill StWoburn, MA 01801
305 Salem St
WoburnMA01801
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$2,3001 Bedroom Apartments Available Oct 1
70 Mill St, Unit 2
70 Mill StWoburn, MA 01801
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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$2,3001 Bedroom Apartments Available Now
70 Mill St, Unit 10
70 Mill StWoburn, MA 01801
Showing Results 1-16, Page 1 of 1
Winchester Highlands, Winchester, MA Local Guide
How much does it cost to rent a home in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,740 | $1,000 | $3,500 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,800 | $2,900 | $5,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $4,333 | $3,500 | $5,500 |
| Winchester Highlands 5 Bedroom Homes for Rent | $10,450 | $4,850 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $7,500 | $7,500 | $7,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 16 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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Best Value Homes for Rent in Winchester Highlands, MA
As of September 22, 2026 the best value rental home in the Winchester Highlands area is the $0.26 price per square foot 177 Central St Model at 177 Central St in the Nobility Hill neighborhood starting from $2,600. The second greatest value Winchester Highlands rental home is the 6 Johnson St Model at 6 Johnson St in the Walnut Hill neighborhood starting at $4,000 with a $2.00 price per square foot. Here is today’s list of the best values for Winchester Highlands homes based on price per square foot:
| Home Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 177 Central St | 177 Central St | 2BR, 1BA | $0.26 |
| 6 Johnson St | 6 Johnson St | 4BR, 1BA | $2.00 |
| 289 Elm St, Unit 14 | 289 Elm St | 2BR, 2BA | $2.22 |
| 63 Holland St | 63 Holland St | 2BR, 1BA | $3.50 |
| 74 Beach St, Unit 5-1 | 74 Beach St | 1BR, 1BA | $2.18 |
| 200 Swanton St, Unit 313 | 200 Swanton St | 1BR, 1BA | $3.55 |
| 84 Franklin St, Unit 2 | 84 Franklin St | 1BR, 1BA | $3.62 |
| 200 Swanton St, Unit 708 | 200 Swanton St | Studio, 1BA | $4.73 |
| 200 Swanton St, Unit 240 | 200 Swanton St | 1BR, 1BA | $4.55 |
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 116 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,750 to $12,539. There are also 52 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,000 to $15,000.
What is the current price range for Rental Homes in Winchester Highlands?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester Highlands ranges from $1,000 to $15,000 with an average monthly rent of $3,704.
How much are larger Three and Four Bedroom Rentals in Winchester Highlands?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester Highlands range from $3,200 to $7,312, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,500 and Four Bedroom Apartments start at $3,700.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
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