0 Green St
WoburnMA01801
Cheap Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA from $1,200 (12 Rentals)
Search the lowest-cost Homes available for rent right now in the Winchester Highlands area of Winchester.
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
74 Beach St, Unit Continental Court
74 Beach St
WoburnMA01801
1 Continental Ct
WoburnMA01801
200 Swanton St
WinchesterMA01890
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.
74 Beach St
WoburnMA01801
71 Montvale Ave
StonehamMA02180
80 N Warren St
WoburnMA01801
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74 Beach St
WoburnMA01801
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.
71 Montvale Ave
StonehamMA02180
Showing Results 1-12, 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 | $2,795 | $2,200 | $3,750 |
| Winchester Highlands 3 Bedroom Homes for Rent | $3,672 | $2,900 | $4,800 |
| Winchester Highlands 4 Bedroom Homes for Rent | $5,459 | $3,825 | $8,000 |
| Winchester Highlands 5 Bedroom Homes for Rent | $6,411 | $4,600 | $10,000+ |
| Winchester Highlands 6 Bedroom Homes for Rent | $13,500 | $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 12 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.
Explore Winchester
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 $1,900. The Devon at Weiss Farm has the second lowest priced unit, which is a Studio apartment currently listed from $2,290. 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 | $1,900 |
| The Devon at Weiss Farm | Studio | Studio,1BA | $2,290 |
| Hanover Stoneham | Ea | 1BR,1BA | $2,431 |
Best Value Apartments for Rent in Winchester Highlands, MA
As of September 10, 2025 the best value apartment in the Winchester Highlands area is the $0.53 price per square foot 476 Fulton St Model at 476 Fulton St, Unit 1 in the in the Ferryway neighborhood starting from $5,295. The second greatest value Winchester Highlands apartment is the 8 Cross St Model at 8 Cross St, Unit 1 starting at $3,300 with a $0.33 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. |
|---|---|---|---|
| 476 Fulton St, Unit 1 | 476 Fulton St | 5BR,4.5BA | $0.53 |
| 8 Cross St, Unit 1 | 8 Cross St | 3BR,1.5BA | $0.33 |
| 286 Main St, Unit 3 | 286 Main St | 2BR,2BA | $2.36 |
| 22 Scott St, Unit 1 | 22 Scott St | 2BR,1BA | $2.40 |
| 159 Main St | 159 Main St | 2BR,2BA | $2.67 |
| 7 Boline Pl, Unit 1 | 7 Boline Pl | 1BR,1BA | $2.30 |
| 343 Washington St, Unit 343 | 343 Washington St | 2BR,1BA | $2.74 |
| Mill Street Gardens | 2 Bedroom | 2BR,1BA | $2.65 |
| 56 Campbell St, Unit 56R | 56 Campbell St | 2BR,1BA | $2.88 |
| 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
3.5Pet Friendly
Frequently Asked Questions about Winchester Highlands
What type of rentals are currently available in Winchester Highlands?
There are currently 119 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $1,550 to $7,500. There are also 71 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,200 to $13,500.
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 $1,200 to $13,500 with an average monthly rent of $5,080.
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.
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.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.