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$9503 Bedroom Apartments Available Now
13 Center St, Unit 2
13 Center StWoburn, MA 01801
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,900 (17 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St
WinchesterMA01890
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
33 Montvale Ave, Unit #3
33 Montvale Ave
WoburnMA01801
60 Franklin St
StonehamMA02180
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
71 Montvale Ave
StonehamMA02180
80 N Warren St
WoburnMA01801
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$2,1501 Bedroom Apartments Available Now
52 Mill St, Unit 11
52 Mill StWoburn, MA 01801
74 Beach St
WoburnMA01801
320 Fellsview Terrace
StonehamMA02180
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St, Unit 11
50 Mill StWoburn, MA 01801
29 -2 Arlington Rd, Unit 6
29 -2 Arlington Rd
WoburnMA01801
558 Main St
StonehamMA02180
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
39 Franklin St
WoburnMA01801
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
220 Central St
StonehamMA02180
202 Central St
StonehamMA02180
Showing Results 1-17, 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 | $2,999 | $2,400 | $4,200 |
| Winchester Highlands 3 Bedroom Homes for Rent | $4,013 | $2,500 | $6,500 |
| Winchester Highlands 4 Bedroom Homes for Rent | $6,221 | $2,900 | $10,000+ |
| Winchester Highlands 5 Bedroom Homes for Rent | $12,381 | $5,295 | $10,000+ |
| Winchester Highlands 7 Bedroom Homes for Rent | $11,000 | $10,000 | $10,000+ |
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 17 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 |
| 7-1 Kilby St | 1 Bedroom | 1BR,1BA | $2,300 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,483 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of June 22, 2026 the best value apartment in the Winchester Highlands area is the $2.03 price per square foot 10 Webster St Model at 10 Webster St, Unit 1 in the in the North Medford neighborhood starting from $4,000. The second greatest value Winchester Highlands apartment is the 286 Main St Model at 286 Main St, Unit 3 starting at $2,995 with a $2.36 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. |
|---|---|---|---|
| 10 Webster St, Unit 1 | 10 Webster St | 4BR,2BA | $2.03 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 6 Munroe St, Unit 2 | 6 Munroe St | 3BR,2BA | $0.89 |
| 107 Belle Ave | 107 Belle Ave | 3BR,1BA | $3.13 |
| The Mave | B2AP | 2BR,2BA | $3.35 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 79 Montvale Ave | Two Bedroom | 2BR,1BA | $3.33 |
| Alta Clara | 1E1 | 1BR,1BA | $3.60 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 7-1 Kilby St | 1 Bedroom | 1BR,1BA | $3.54 |
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 113 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $950 to $11,016. There are also 54 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,900 to $25,000.
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 $1,900 to $25,000 with an average monthly rent of $6,435.
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 $950 to $6,704, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $2,900.
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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