200 Swanton St
WinchesterMA01890
Cheap Homes for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,800 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
35 Prospect St
WoburnMA01801
74 Beach St, Unit 5-1
74 Beach St
WoburnMA01801
74 Beach St
WoburnMA01801
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$2,0501 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 1
2 Elmwood AveWinchester, MA 01890
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
200 Swanton St, Unit 412
200 Swanton St
WinchesterMA01890
8 Mason St
WinchesterMA01890
200 Swanton St, Unit 228
200 Swanton St
WinchesterMA01890
426 Main St
StonehamMA02180
22 Emerson St
StonehamMA02180
35 Arlington St
WoburnMA01801
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.
182 Central St
StonehamMA02180
Showing Results 1-13, 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 | $2,896 | $2,300 | $3,700 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,783 | $2,900 | $6,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,532 | $2,850 | $10,000+ |
| Winchester Highlands 5 Bedroom Homes for Rent | $8,598 | $5,295 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $8,500 | $8,500 | $8,500 |
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 13 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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Cheapest Available Winchester Highlands Apartments for Rent
The cheapest available apartment rental in the Winchester Highlands area of Boston, MA is a 1 Bed unit found at Mill Street Gardens priced from $1,950. 2-15 Winn Park has the second lowest priced unit, which is a Studio apartment currently listed from $2,050. Here are the most affordable Winchester Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
| 30 Pomeworth Street | 2BR/1.0BA | 2BR,1BA | $2,295 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of August 07, 2026 the best value apartment in the Winchester Highlands area is the $2.31 price per square foot 722 Highland Ave Model at 722 Highland Ave, Unit 2 in the in the Ferryway neighborhood starting from $3,000. The second greatest value Winchester Highlands apartment is the 14 Salem St Model at 14 Salem St starting at $2,600 with a $2.26 price per square foot in the Walnut Hill neighborhood. Here is today’s list of the best values for Winchester Highlands apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 722 Highland Ave, Unit 2 | 722 Highland Ave | 3BR,2BA | $2.31 |
| 14 Salem St | 14 Salem St | 2BR,1BA | $2.26 |
| 48 Nashua St, Unit 2 | 48 Nashua St | 2BR,1BA | $2.27 |
| 32 Pond St, Unit 2w | 32 Pond St | 2BR,1BA | $2.45 |
| 32 Pond St, Unit 2 | 32 Pond St | 2BR,1BA | $2.45 |
| 79 Montvale Ave | 1 Bedroom | 1BR,1BA | $2.40 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 103 Pleasant St, Unit 2 | 103 Pleasant St | 1BR,1BA | $2.37 |
| 7 Mishawum Rd, Unit Unit B | 7 Mishawum Rd | 1BR,1BA | $2.39 |
| 103 Pleasant St, Unit 2l | 103 Pleasant St | 1BR,1BA | $2.53 |
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 $1,695 to $20,951. There are also 59 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,800 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 $1,800 to $15,000 with an average monthly rent of $4,167.
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 $2,800 to $5,628, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,850 and Four Bedroom Apartments start at $3,500.
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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