
Cheap Apartments for Rent in Winchester, MA from $900 (63 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.


Total Monthly Price
219 Washington St, Unit 3

Elmwood Apartments

Total Monthly Price
195 Forest St

1334 Massachusetts Ave

Total Monthly Price
48 Nashua St, Unit 1

Old Colony Apartments

182 Central St

Leisure Lane Apartments

Brattle Drive Apartments
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7 Old Colony Ln

1080 Massachusetts Ave

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76 Winter St, Unit B

29 Arlington Rd

71-73 Winn St

Total Monthly Price
224 Main St, Unit 1B

385 Massachusetts Ave

385 Massachusetts Ave

Total Monthly Price
375 Main St, Unit 33

35 Prospect St
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2-15 Winn Park

12 Brattle Dr

Mill Street Gardens

27 Salem St

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7 Court St, Unit 1 - J

Total Monthly Price
7 Court St, Unit 1

20 Stephenson Aman Street

Total Monthly Price
Arlington Gardens Apartments

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279 Massachusetts Ave, Unit 1

276 Massachusetts Ave
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Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

276 Massachusetts Ave

Total Monthly Price
286 Massachusetts Ave, Unit #207

3 Forest St

Tudor Glen Village

284 Montvale Ave

26 Park St

371 Main St

Total Monthly Price
4 Colonial Village Dr, Unit 4

5 Boston Ave

Total Monthly Price
The Devon at Weiss Farm
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Total Monthly Price
74 Beach St, Unit #3-3

Total Monthly Price
25 Arlington Rd, Unit Apt 1-1

GlenBrook Estates

385 Massachusetts Ave

200 Bedford Rd

50 Cambridge Rd

Mill Street Heights

Total Monthly Price
121 Winthrop St, Unit #1

1 Wyman St

9 Ryder St
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Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cheap Winchester Studio Apartments | $2,153 | $1,400 | $2,900 |
| Cheap Winchester 1 Bedroom Apartments | $2,638 | $1,850 | $4,195 |
| Cheap Winchester 2 Bedroom Apartments | $3,262 | $1,925 | $5,340 |
| Cheap Winchester 3 Bedroom Apartments | $3,656 | $2,500 | $5,595 |
| Cheap Winchester 4 Bedroom Apartments | $4,348 | $900 | $5,600 |
| Winchester 5 Bedroom Apartments | $6,138 | $4,500 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,167 | $5,945 | $8,437 |
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
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Cheapest Available Winchester Apartments for Rent
 The cheapest available apartment rental in Winchester, MA is a 1 Bed unit found at Elmwood Apartments in the Nobility Hill neighborhood priced from $1,750. Old Colony Apartments in the Rock Meadow neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,750. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Elmwood Apartments | Studio 250 sf | 1BR,1BA | $1,750 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Leisure Lane Apartments | studio | Studio,1BA | $1,795 |
| Brattle Drive Apartments | Studio | Studio,1BA | $1,800 |
| 71-73 Winn St | One Bedroom | 1BR,1BA | $1,900 |
| 2-15 Winn Park | Studio | Studio,1BA | $1,950 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
Best Value Apartments for Rent in Winchester, MA
As of February 06, 2026 the best value apartment in the Winchester area is the $0.30 price per square foot 1 Victoria St Model at 1 Victoria St, Unit 1A in the in the Strawberry Hill neighborhood starting from $2,975. The second greatest value Winchester apartment is the 96 Conwell Ave Model at 96 Conwell Ave, Unit 1 starting at $3,000 with a $0.30 price per square foot in the Strawberry Hill neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 1 Victoria St, Unit 1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 124 Forest St, Unit 2 | 124 Forest St | 3BR,1BA | $0.30 |
| 195 Forest St | 195 Forest St | 4BR,2.5BA | $0.31 |
Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read ArticleDon'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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
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Read ArticleCash 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.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleQuick 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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Cheap Winchester Apartments
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at Old Colony Apartments listed at $1,750.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,750 at Elmwood Apartments.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,200 at Arlington Gardens Apartments.
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.
Helpful Local Expert Guides

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.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.