$1,725
Total Monthly Price12 Month Lease Term
Total Monthly Price
Base Rent
$1,725
Utilities & Essentials
Varies
Total Monthly Price
$1,725
1 Bedroom, 1 Bath Townhome for Rent
Available Now
48 Warren Ave
WoburnMA01801
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,700 (21 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
48 Warren Ave
WoburnMA01801
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60 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
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157 Franklin St
StonehamMA02180
14 Church Ave
WoburnMA01801
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.
14 Church Ave
WoburnMA01801
200 Swanton St
WinchesterMA01890
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35 Prospect St, Unit 35 Prospect St # 102
35 Prospect St
WoburnMA01801
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100 Ledgewood Dr, Unit 216
100 Ledgewood Dr
StonehamMA02180
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
200 Swanton St
WinchesterMA01890
25 Arlington Rd
WoburnMA01801
6 Skillings Rd
WinchesterMA01890
177 Central St
StonehamMA02180
144 Marble St
StonehamMA02180
4 Albert Dr, Unit 11
4 Albert Dr
WoburnMA01801
35 Montvale Ave
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.
Showing Results 1-21, 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 Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands 2 Bedroom Homes for Rent | $2,999 | $2,200 | $5,700 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,487 | $3,000 | $4,200 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,067 | $3,890 | $6,460 |
| Winchester Highlands 5 Bedroom Homes for Rent | $5,759 | $2,800 | $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 21 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
- Nearby Winchester neighborhoods
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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. The Devon at Weiss Farm has the second lowest priced unit, which is a Studio apartment currently listed from $2,272. 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 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,272 |
| Mill Street Heights | B | 1BR,1BA | $2,275 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of December 12, 2025 the best value apartment in the Winchester Highlands area is the $0.25 price per square foot 8 Cross St Model at 8 Cross St, Unit 1 in the in the Walnut Hill neighborhood starting from $2,500. The second greatest value Winchester Highlands apartment is the 223 Central St Model at 223 Central St, Unit 7 starting at $2,000 with a $0.20 price per square foot in the West Side 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. |
|---|---|---|---|
| 8 Cross St, Unit 1 | 8 Cross St | 3BR,1.5BA | $0.25 |
| 223 Central St, Unit 7 | 223 Central St | 1BR,1BA | $0.20 |
| 21 Franklin St, Unit 1FRT | 21 Franklin St | 3BR,1.5BA | $2.14 |
| Lofts at 307 Main LLC | 2BR/1.5BA | 2BR,1.5BA | $2.14 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 37 Arlington St, Unit 1R | 37 Arlington St | 1BR,1BA | $2.11 |
| 25 Arlington Rd, Unit Apt 1-1 | 25 Arlington Rd | 2BR,1BA | $2.64 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 37 Arlington St, Unit 1R-J | 37 Arlington St | 1BR,1BA | $2.53 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 115 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,780 to $6,900. There are also 57 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,725 to $7,500.
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 $1,725 to $7,500 with an average monthly rent of $3,535.
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 $2,500 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,890 and Four Bedroom Apartments start at $4,150.
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.
Helpful Local Expert Guides
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
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Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.