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$1,550
Total Monthly Price12 Month Lease Term
Studio Apartment Available Dec 1Total Monthly Price
Base Rent
$1,550
Total Monthly Price
$1,550
219 Washington St, Unit 8
219 Washington StWinchester, MA 01890
Cheap Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA from $1,400 (11 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winchester Highlands area of Winchester.
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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
7 Court St, Unit 1
7 Court StWoburn, 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
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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$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
455 Main St
StonehamMA02180
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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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Showing Results 1-11, 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 | $2,383 | $1,550 | $2,819 |
| Winchester Highlands 1 Bedroom Apartments | $2,922 | $1,895 | $4,195 |
| Winchester Highlands 2 Bedroom Apartments | $3,699 | $2,250 | $4,872 |
| Winchester Highlands 3 Bedroom Apartments | $4,745 | $2,980 | $5,329 |
| Winchester Highlands 4 Bedroom Apartments | $4,400 | $4,400 | $4,400 |
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 11 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
- Nearby Cities
- ZIP codes
- Local Counties
- 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. The Devon at Weiss Farm has the second lowest priced unit, which is a Studio apartment currently listed from $2,247. 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 | $2,247 |
| 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 October 14, 2025 the best value apartment in the Winchester Highlands area is the $2.20 price per square foot 11 Garfield Ave Model at 11 Garfield Ave, Unit 1 in the in the Walnut Hill neighborhood starting from $4,400. 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. |
|---|---|---|---|
| 11 Garfield Ave, Unit 1 | 11 Garfield Ave | 4BR,3BA | $2.20 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 107 Belle Ave | 107 Belle Ave | 3BR,1BA | $3.13 |
| 4 Center St, Unit 2 | 4 Center St | 2BR,1.5BA | $2.65 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 25 Arlington Rd, Unit Apt 1-1 | 25 Arlington Rd | 2BR,1BA | $2.64 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 7 Court St, Unit 1 | 7 Court St | 1BR,1BA | $2.37 |
| 74 Beach St, Unit Unit #3-3 | 74 Beach St | 2BR,1BA | $2.87 |
| 8 Eastern Ave, Unit Thirdfloor | 8 Eastern Ave | 1BR,1BA | $2.79 |
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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
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 $2,247.
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 The Devon at Weiss Farm and starts from $4,198.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.