200 Swanton St
WinchesterMA01890
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,800 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
157 Franklin St
StonehamMA02180
157 Franklin St
StonehamMA02180
200 Swanton St, Unit 704
200 Swanton St
WinchesterMA01890
538 Main St
StonehamMA02180
35 Vine St
WinchesterMA01890
35 Prospect St
WoburnMA01801
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
27 -2 Arlington Rd
WoburnMA01801
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
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Winchester Highlands, Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester Highlands?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,831 | $2,500 | $3,800 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,375 | $2,800 | $4,200 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,281 | $4,800 | $6,000 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,920 | $2,800 | $7,000 |
Browse Homes for Rent in this Neighborhood
There are currently 9 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
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Winchester Highlands, Winchester, MA Local Guide
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Cheapest Available Winchester Highlands Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2,250 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of March 30, 2025 the best value apartment in the Winchester Highlands area is the $0.53 price per square foot 480 Fulton St Model at 480 Fulton St, Unit Right in the in the Ferryway neighborhood starting from $5,300. The second greatest value Winchester Highlands apartment is the 181 Central St Model at 181 Central St, Unit #11 starting at $2,400 with a $0.24 price per square foot in the Nobility 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. |
|---|---|---|---|
| 480 Fulton St, Unit Right | 480 Fulton St | 4BR,4.5BA | $0.53 |
| 181 Central St, Unit #11 | 181 Central St | 2BR,1BA | $0.24 |
| 9 Carter Pl, Unit Carter Place | 9 Carter Pl | 4BR,2BA | $2.07 |
| 834 Main St, Unit 834 | 834 Main St | 2BR,1BA | $2.22 |
| 2 Evans St, Unit 1 | 2 Evans St | 2BR,1BA | $2.27 |
| 25R Auburn St | 25R Auburn St | 2BR,1BA | $2.36 |
| 2 Fremont St, Unit 1 | 2 Fremont St | 2BR,1BA | $1.84 |
| 35 Montvale Ave | 35 Montvale Ave | 2BR,1BA | $1.75 |
| 4 Stone Ave, Unit #1H | 4 Stone Ave | 1BR,1BA | $2.48 |
| 7 Boline Pl, Unit 1 | 7 Boline Pl | 1BR,1BA | $2.30 |
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Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 148 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,750 to $7,135. There are also 65 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,895 to $7,000.
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 $1,895 to $7,000 with an average monthly rent of $3,608.
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 $7,135, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $4,200. Four Bedroom Single-Family rentals are also available starting from $4,800 and Four Bedroom Apartments start at $4,200.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.