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Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (23 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
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$1,850
Total Monthly Price12 Month Lease Term
Studio Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$1,850
Total Monthly Price
$1,850
219 Washington St, Unit 11
219 Washington StWinchester, MA 01890
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57 Pleasant St
WoburnMA01801
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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,895
Total Monthly Price
$1,895
37 Arlington St, Unit 1R
37 Arlington StWoburn, MA 01801
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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$1,895
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$1,895
Total Monthly Price
$1,895
37 Arlington St, Unit 1R-J
37 Arlington StWoburn, MA 01801
29 Arlington Rd
WoburnMA01801
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$1,950
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,950
Total Monthly Price
$1,950
8 Eastern Ave, Unit Thirdfloor
8 Eastern AveWoburn, MA 01801
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Rent Specials
$1,950 - $2,350
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
121 Franklin St
StonehamMA02180
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$2,000
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$2,000
Total Monthly Price
$2,000
223 Central St, Unit 7
223 Central StStoneham, MA 02180
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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.
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$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
25 Arlington Rd, Unit Apt 1-1
25 Arlington RdWoburn, MA 01801
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$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
74 Beach St, Unit #3-3
74 Beach StWoburn, MA 01801
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Rent Specials
$2,267 - $5,415
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,267 - $5,415
Total Monthly Price
$2,267 - $5,415
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
59 Mill St
WoburnMA01801
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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.
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Showing Results 1-23, 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 an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,340 | $1,500 | $2,829 |
| Winchester Highlands 1 Bedroom Apartments | $2,801 | $1,895 | $4,195 |
| Winchester Highlands 2 Bedroom Apartments | $3,597 | $2,250 | $4,740 |
| Winchester Highlands 3 Bedroom Apartments | $4,467 | $2,500 | $6,900 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 23 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
See all Apartments in WinchesterExplore Winchester
Winchester Highlands, Winchester, MA Local Guide
- Nearby Winchester neighborhoods
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- School Districts
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. Mill Street Heights has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,225. 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 |
| Mill Street Heights | B | 1BR,1BA | $2,225 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,267 |
| 44 Montvale Avenue | Studio | Studio,1BA | $2,380 |
| Hanover Stoneham | Ga | 1BR,1BA | $2,431 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of November 29, 2025 the best value apartment in the Winchester Highlands area is the $0.28 price per square foot 8 Cross St Model at 8 Cross St in the in the Walnut Hill neighborhood starting from $2,800. The second greatest value Winchester Highlands apartment is the 21 Franklin St Model at 21 Franklin St, Unit 1FRT starting at $3,000 with a $2.14 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. |
|---|---|---|---|
| 8 Cross St | 8 Cross St | 3BR,2BA | $0.28 |
| 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 |
| 48 Pleasant Street | 2BR/1.5BA | 2BR,1.5BA | $2.82 |
| 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 |
| 8 Eastern Ave, Unit Thirdfloor | 8 Eastern Ave | 1BR,1BA | $2.79 |
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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Pet Friendly LifestyleWinchester Highlands, Winchester, MA
Ranked #1
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Getting Around the Winchester Highlands Neighborhood in Winchester, MA
Walk Score®
44 / 100
Car-Dependent
Most errands require a car
Bike Score®
65 / 100
Bikeable
Some bike infrastructure
Transit Score®
5 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winchester Highlands Apartments
What is the Cheapest Studio apartment in Winchester Highlands?
Currently the most affordable Cheap Studio Apartment in Winchester Highlands is at The Devon at Weiss Farm listed at $2,267.
How much is rent for a Cheap One Bedroom Winchester Highlands Apartment?
The lowest price for a Cheap One Bedroom Winchester Highlands Apartment is $1,950 at Mill Street Gardens.
What is the lowest price for a Cheap Two Bedroom Winchester Highlands Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester Highlands is starting from $2,250 at Mill Street Gardens.
What is the most affordable Winchester Highlands Three Bedroom Apartment?
The best deal on a cheap Winchester Highlands Three Bedroom Apartment rental is at Mill Street Heights and starts from $3,225.
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.
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.