2 Bedroom Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (45 Rentals)

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property at 36 Cross St

36 Cross St

WinchesterMA01890
property at 343 Washington St

343 Washington St

WinchesterMA01890
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7 Conant Rd
2 Bedroom Apartments

7 Conant Rd

7 Conant RdWinchester, MA 01890
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The Village
2 Bedroom Apartments

The Village

171 Swanton StWinchester, MA 01890
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10 Winchester Plz
2 Bedroom Apartments

10 Winchester Plz

10 Winchester PlzWinchester, MA 01890
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40 Elmwood Ave
2 Bedroom Apartments

40 Elmwood Ave

40 Elmwood AveWinchester, MA 01890
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The Devon at Weiss Farm
Rent Specials
$3,253 - $3,869
Total Monthly Price

Total Monthly Price

Base Rent
$2,267 - $5,415

Total Monthly Price
$2,267 - $5,415
2 Bedroom Apartments Available Now

The Devon at Weiss Farm

168 Franklin StStoneham, MA 02180
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  • Customer Reviewed
  • Utilities Included

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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The Mave
Rent Specials
$3,085 - $4,740
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,465 - $4,740

Total Monthly Price
$2,465 - $4,740
2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
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  • Customer Reviewed
  • Matterport 3D Tour
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Alta Clara
$3,193 - $3,941
Total Monthly Price

Total Monthly Price

Base Rent
$2,606 - $6,435

Total Monthly Price
$2,606 - $6,435
2 Bedroom Apartments Available Now

Alta Clara

21 Executive DrStoneham, MA 02180
Luxury
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159 Main St
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600
2 Bedroom Apartment Available Now

159 Main St

159 Main StStoneham, MA 02180

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property at 224 Park St

224 Park St

StonehamMA02180
property at 228 Main St

228 Main St

StonehamMA02180
property at 29 Garfield Ave

29 Garfield Ave

WoburnMA01801
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11 N Warren Ave
2 Bedroom Apartments

11 N Warren Ave

11 N Warren AveWoburn, MA 01801
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Village Estates
2 Bedroom Apartments

Village Estates

201 Main StWoburn, MA 01801

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Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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39 Chestnut St
2 Bedroom Apartments

39 Chestnut St

39 Chestnut StStoneham, MA 02180
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33 Center St
2 Bedroom Apartments

33 Center St

33 Center StWoburn, MA 01801
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177 Franklin St
2 Bedroom Apartments

177 Franklin St

177 Franklin StStoneham, MA 02180
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Franklin Condo
2 Bedroom Apartments

Franklin Condo

179 Franklin StStoneham, MA 02180
  • Utilities Included
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Hillside Gardens
2 Bedroom Apartments

Hillside Gardens

101-116 Hill StStoneham, MA 02180
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395 Main St
2 Bedroom Apartments

395 Main St

395 Main StStoneham, MA 02180
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The Terraces
2 Bedroom Apartments

The Terraces

12 Hillside RdStoneham, MA 02180

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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588 Main St
2 Bedroom Apartments

588 Main St

588 Main StStoneham, MA 02180
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13 Pomeworth St
2 Bedroom Apartments

13 Pomeworth St

13 Pomeworth StStoneham, MA 02180
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Stoneham House
2 Bedroom Apartments

Stoneham House

180-222 Central StStoneham, MA 02180
  • Utilities Included
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411 Main St
2 Bedroom Apartments

411 Main St

411 Main StStoneham, MA 02180
  • Utilities Included
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59 Mill St
2 Bedroom Apartments

59 Mill St

59 Mill StWoburn, MA 01801
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Colonial Court
2 Bedroom Apartments

Colonial Court

132-136 Main StStoneham, MA 02180
  • Utilities Included
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47 Prospect St
2 Bedroom Apartments

47 Prospect St

47 Prospect StWoburn, MA 01801
  • Utilities Included

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

Winchester Highlands, Winchester, MA Local Guide

Largest Available Winchester Highlands 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in the Winchester Highlands area of Boston, MA is found at Lofts at 307 Main LLC and is listed at 1,400 square feet priced from $2,995. Here is today’s list of the largest available 2 Bedroom units in the area:

Apartment ListingModel NameSquare FootagePriced From
Lofts at 307 Main LLC2BR/1.5BA1,400 Sq Ft$2,995
Sanctuary Winchester North2J Den1,355 Sq Ft$4,007
Hanover StonehamM1,322 Sq Ft$4,618
Alta Clara2H1,192 Sq Ft$3,533
The MaveB2BP1,112 Sq Ft$3,275

Cheapest Available Winchester Highlands 2 Bedroom Apartments

Currently the lowest priced 2 Bedroom apartment unit Winchester Highlands of Boston, MA is the 2 Bedroom Model starting from $2,250 at Mill Street Gardens. The average price for all 2 Bedroom apartments in Winchester Highlands is currently $3,607. Here is today’s list of the cheapest available 2 Bedroom options in the area:

Apartment ListingModel NamePriced From
Mill Street Gardens2 Bedroom$2,250
Mill Street HeightsD$2,850
Lofts at 307 Main LLC2BR/1.5BA$2,995
48 Pleasant Street2BR/1.5BA$2,995
The MaveB2AP$3,085
The Devon at Weiss Farm2 Bed 2 Bath$3,253

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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Quick Rent Budget Calculator

How much rent can you afford?

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 Lifestyle
Winchester Highlands, Winchester, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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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

Frequently Asked Questions about 2 Bedroom Winchester Highlands Apartments

What is the Cheapest apartment in Winchester Highlands with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winchester Highlands is at Mill Street Gardens listed at $2,250.

How much is the average rent for a 2 Bedroom Winchester Highlands Apartment?

The average rent for a 2 Bedroom Apartment in Winchester Highlands is $3,607.

What is the largest available 2 Bedroom Winchester Highlands Apartment for rent?

Today's apartment with the most square footage in Winchester Highlands is a 1,400 square feet unit starting from $2,995 at Lofts at 307 Main LLC.

What is the average size for Winchester Highlands 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winchester Highlands is currently 2,091 sq ft.

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.

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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.

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Apartment Common Area Rules: What Renters Need to Know

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.