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$2,000
Total Monthly Price12 Month Lease Term
Studio Apartment Available Jul 1Total Monthly Price
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$2,000
Total Monthly Price
$2,000
219 Washington St, Unit 2
219 Washington StWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $900 (43 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
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1 Bedroom Apartments
Elmwood Apartments
2 Elmwood AveWinchester, MA 01890
200 Swanton St
WinchesterMA01890
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$9503 Bedroom Apartments Available Now
13 Center St, Unit 2
13 Center StWoburn, MA 01801
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$1,065
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
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$1,065
Total Monthly Price
$1,065
6 Munroe St, Unit 2
6 Munroe StWoburn, MA 01801
568 Main St
WoburnMA01801
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$1,750 - $2,450
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartment Available Jul 1Total Monthly Price
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$1,750 - $2,450
Total Monthly Price
$1,750 - $2,450
48 Nashua St
48 Nashua StWoburn, MA 01801
48 Warren Ave
WoburnMA01801
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
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33 Montvale Ave, Unit #3
33 Montvale Ave
WoburnMA01801
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$1,950 - $2,700
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
12 Gould St
StonehamMA02180
21 Spring St
StonehamMA02180
19 Spring St
StonehamMA02180
11 Main St
WoburnMA01801
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$2,050
Plus Fees1 Month Lease Term
Studio Apartments Available Now2-15 Winn Park
2-15 Winn ParkWoburn, MA 01801
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$2,1501 Bedroom Apartments Available Now
52 Mill St, Unit 11
52 Mill 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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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
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$2,200
Total Monthly Price
$2,200
491 Main St, Unit 2br apartment
491 Main StWoburn, MA 01801
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$2,256 - $5,408
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Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
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$2,256 - $5,408
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Hanover Stoneham
95 Maple StStoneham, MA 02180
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$2,300 - $2,350
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available Now7-1 Kilby St
7 Kilby StWoburn, MA 01801
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$2,380 - $2,800
Plus Fees1 Month Lease Term
Studio to 1 Bedroom Apartments Available Now44 Montvale Avenue
44 Montvale AveWoburn, MA 01801
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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
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$2,483 - $4,329
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,483 - $4,329
Total Monthly Price
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The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
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.
99 Garfield Ave
WoburnMA01801
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$2,600
Total Monthly Price
$2,600
159 Main St
159 Main StStoneham, MA 02180
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
25 Arlington Rd, Unit Apt #3 6
25 Arlington RdWoburn, MA 01801
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$2,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
14 Salem St, Unit 3
14 Salem StWoburn, MA 01801
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1 Bedroom Apartments
667 Main St
667 Main StWoburn, MA 01801
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1 to 2 Bedroom Apartments
411 Main St
411 Main StStoneham, MA 02180
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1 Bedroom Apartments
71-73 Winn St
71-73 Winn StWoburn, MA 01801
84 Franklin St, Unit 2
84 Franklin St
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.
60 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
80 N Warren St
WoburnMA01801
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Studio to 2 Bedroom Apartments
Stoneham House
180-222 Central StStoneham, MA 02180
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1 to 2 Bedroom Apartments
30 Pomeworth Street
30 Pomeworth StStoneham, MA 02180
74 Beach St
WoburnMA01801
320 Fellsview Terrace
StonehamMA02180
39 Franklin St
WoburnMA01801
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
558 Main St
StonehamMA02180
220 Central St
StonehamMA02180
202 Central St
StonehamMA02180
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Winchester Highlands, Winchester, MA Local Guide
How much does it cost to rent an apartment in Winchester Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Highlands Studio Apartments | $2,362 | $1,700 | $2,700 |
| Winchester Highlands 1 Bedroom Apartments | $3,005 | $1,850 | $4,215 |
| Winchester Highlands 2 Bedroom Apartments | $3,665 | $2,200 | $5,440 |
| Winchester Highlands 3 Bedroom Apartments | $3,931 | $950 | $6,704 |
| Winchester Highlands 4 Bedroom Apartments | $3,550 | $2,900 | $4,000 |
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 43 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 |
| Hanover Stoneham | Ca | 1BR,1BA | $2,563 |
| 79 Montvale Ave | Two Bedroom | 2BR,1BA | $3,000 |
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 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 2-15 Winn Park listed at $2,050.
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 Hanover Stoneham and starts from $5,408.
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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The 10 Best Affordable Neighborhoods in Boston, MA
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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
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Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.