107 Belle Ave
MedfordMA02155
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $900 (10 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
43 Pomeworth St
StonehamMA02180
43 Pomeworth St, Unit 34
43 Pomeworth St
StonehamMA02180
35 Prospect St
WoburnMA01801
200 Swanton St, Unit 704
200 Swanton St
WinchesterMA01890
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
35 Vine St
WinchesterMA01890
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
31 Arlington Rd, Unit 5
31 Arlington Rd
WoburnMA01801
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
345 Washington 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
Showing Results 1-10, Page 1 of 1
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 | $2,900 | $2,400 | $4,200 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,530 | $3,050 | $4,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,340 | $4,995 | $6,000 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,918 | $5,495 | $7,000 |
| Winchester Highlands 6 Bedroom Homes for Rent | $7,500 | $5,500 | $9,500 |
| Winchester Highlands 7 Bedroom Homes for Rent | $11,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 10 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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Best Value Apartments for Rent in Winchester Highlands, MA
As of April 17, 2025 the best value apartment in the Winchester Highlands area is the $0.18 price per square foot 36 Montvale Ave Model at 36 Montvale Ave in the in the Walnut Hill neighborhood starting from $1,750. The second greatest value Winchester Highlands apartment is the 480 Fulton St Model at 480 Fulton St, Unit Right starting at $5,300 with a $0.53 price per square foot in the Ferryway 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. |
|---|---|---|---|
| 36 Montvale Ave | 36 Montvale Ave | 2BR,1BA | $0.18 |
| 480 Fulton St, Unit Right | 480 Fulton St | 4BR,4.5BA | $0.53 |
| 14 Richardson St, Unit #14x | 14 Richardson St | 2BR,1BA | $1.60 |
| 159 Franklin St, Unit #D3 | 159 Franklin St | 2BR,1BA | $2.27 |
| 2 Fremont St, Unit 1 | 2 Fremont St | 2BR,1BA | $1.84 |
| 15 Church Ave, Unit #2 | 15 Church Ave | 1BR,1BA | $2.00 |
| 75 Church St, Unit #R | 75 Church St | 1BR,1BA | $1.90 |
| 35 Montvale Ave | 35 Montvale Ave | 2BR,1BA | $1.75 |
| 224 Main St, Unit 2 | 224 Main St | 1BR,1BA | $2.06 |
| 24 Arlington Rd, Unit #R | 24 Arlington Rd | 1BR,1BA | $2.00 |
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Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 168 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,400 to $8,000. There are also 54 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $975 to $11,000.
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 $975 to $11,000 with an average monthly rent of $5,455.
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 $8,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,050 to $4,500. Four Bedroom Single-Family rentals are also available starting from $4,995 and Four Bedroom Apartments start at $3,200.
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.
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.
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.