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Rent Specials
$2,597 - $10,242
Plus Fees
1 to 3 Bedroom Apartments Available NowSanctuary Winchester North
25-35 River StWinchester, MA 01890
Luxury Apartments for Rent in Winchester, MA (294 Rentals)
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
145 Washington St, Unit 415
145 Washington StWinchester, MA 01890
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Rent Specials
$3,008 - $20,471
Plus Fees
Studio to 3 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
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$4,150
Total Monthly Price17 Month Lease Term
4 Bedroom Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
10 Webster St, Unit 1
10 Webster StWinchester, MA 01890
29 Harvard St
WinchesterMA01890
415 Washington St
WinchesterMA01890
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36 Cross St
WinchesterMA01890
846 Main St
WinchesterMA01890
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Rent Specials
$1,650 - $2,550
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowBrattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$1,750 - $2,525
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$1,800 - $2,600
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowOld Colony Apartments
1-17 Old Colony LnArlington, MA 02476
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$2,141 - $5,228
Plus Fees
Studio to 3 Bedroom Apartments Available NowHanover Stoneham
95 Maple StStoneham, MA 02180
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$2,195 - $3,295
Plus Fees
1 to 2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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Rent Specials
$2,200 - $2,850
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available NowGlenBrook Estates
200 Bedford RdWoburn, MA 01801
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Rent Specials
$2,252 - $4,950
Total Monthly Price12 Month Lease Term
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,252 - $4,950
Total Monthly Price
$2,252 - $4,950
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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Rent Specials
$2,272 - $5,333
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,272 - $5,333
Total Monthly Price
$2,272 - $5,333
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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$2,275 - $3,500
Plus Fees
1 to 3 Bedroom Apartments Available NowMill Street Heights
59 Mill 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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Rent Specials
$2,465 - $4,880
Total Monthly Price1 Month Lease Term
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,465 - $4,880
Total Monthly Price
$2,465 - $4,880
The Mave
225 Fallon RdStoneham, MA 02180
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$2,495 - $2,550
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now109 Oxford St
109 Oxford StArlington, MA 02474
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$2,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
8 Cross St, Unit 1
8 Cross StWoburn, MA 01801
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$2,500
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
17 Columbus Rd
17 Columbus RdWoburn, MA 01801
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$2,500
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
1 Saint Clare Rd, Unit 4
1 Saint Clare RdMedford, MA 02155
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$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
28 Cornell St, Unit 1
28 Cornell StArlington, MA 02474
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$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
12 Quincy St, Unit 1
12 Quincy StArlington, MA 02476
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$2,500
Total Monthly Price9 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
110 W Quincy St, Unit 1
110 W Quincy StSomerville, MA 02144
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$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 NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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Rent Specials
$2,600 - $3,000
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowStonehill Towers
5 Stonehill DrStoneham, MA 02180
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.
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$2,666 - $4,815
Plus Fees
Studio to 2 Bedroom Apartments Available NowBrigham Square Apartments
30 Mill StArlington, MA 02476
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$2,690
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,690
Total Monthly Price
$2,690
79 Capen St, Unit 1
79 Capen StMedford, MA 02155
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
340 High St, Unit 1
340 High StMedford, MA 02155
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
8 Madison St, Unit 1
8 Madison StMedford, MA 02155
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$2,750
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,750
Total Monthly Price
$2,750
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
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$2,750
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$2,750
Total Monthly Price
$2,750
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
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$2,775
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,775
Total Monthly Price
$2,775
13 Higgins St, Unit 1
13 Higgins StArlington, MA 02476
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
25 Laurel St, Unit 25 Laurel St.
25 Laurel StArlington, MA 02476
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$2,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
26 Marshall St, Unit 1
26 Marshall StMedford, MA 02155
The Art of the Rental Viewing: What to look for during a property tour
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$2,800 - $4,100
Total Monthly Price12 Month Lease Term
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,800 - $4,100
Total Monthly Price
$2,800 - $4,100
The Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
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$2,850
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,850
Total Monthly Price
$2,850
137 Sharon St, Unit 1
137 Sharon StMedford, MA 02155
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$2,850 - $2,950
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now840-846 Massachusetts Ave
840 Massachusetts AveArlington, MA 02476
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$2,895
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now48 Pleasant Street
48 Pleasant StStoneham, MA 02180
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
67 Fairfax St, Unit 1
67 Fairfax StSomerville, MA 02144
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$2,950
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
6 Gloucester St, Unit 2 bedrooms
6 Gloucester StArlington, MA 02476
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$2,950
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
50 Hamilton St, Unit 2
50 Hamilton StMedford, MA 02155
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$2,975
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,975
Total Monthly Price
$2,975
1 Victoria St, Unit 1A
1 Victoria StSomerville, MA 02144
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$2,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,995
Total Monthly Price
$2,995
286 Main St, Unit 3
286 Main StWoburn, MA 01801
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$2,995
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowLofts at 307 Main LLC
307 Main StWoburn, MA 01801
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.
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?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Luxury Studio Apartments | $2,155 | $1,650 | $2,774 |
| Winchester Luxury 1 Bedroom Apartments | $2,637 | $1,750 | $4,195 |
| Winchester Luxury 2 Bedroom Apartments | $3,201 | $1,350 | $4,928 |
| Winchester Luxury 3 Bedroom Apartments | $3,672 | $2,500 | $6,900 |
| Winchester Luxury 4 Bedroom Apartments | $4,463 | $3,300 | $6,375 |
| Winchester 5 Bedroom Apartments | $6,259 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,261 | $5,945 | $8,437 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
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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.
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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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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
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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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See the most popular apartments and homes in Winchester, MA
Getting Around Winchester, MA
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
67 / 100
Bikeable
Some bike infrastructure
Transit Score®
1 / 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 Winchester
How much are Studio apartments in Winchester?
There are currently 102 Studio Apartments in Winchester with rent ranges from $1,650 to $2,774 with an average price of $2,155.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,750 to $4,195 with an average monthly rent of $2,637.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,350 to $4,928. Today's average rental price for Two Bedrooms here is $3,201.
How expensive are Winchester Three Bedroom Apartments?
There are currently 128 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,672 for the location.
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
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
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.
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.