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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$6,250
Total Monthly Price
$6,250
4 High St, Unit 1
4 High StSomerville, MA 02144
5 Bedroom Apartments for Rent in Winchester, MA (42 Rentals)
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$6,250
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5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$6,250
Total Monthly Price
$6,250
4 High St, Unit 4
4 High StSomerville, MA 02144
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$7,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$7,500
Total Monthly Price
$7,500
59 Sunset Rd, Unit 2
59 Sunset RdSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Oct 1Total Monthly Price
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$4,500
Total Monthly Price
$4,500
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,500
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5 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
190 North St, Unit 2
190 North StSomerville, MA 02144
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$7,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$7,000
Total Monthly Price
$7,000
23 Emery St
23 Emery StMedford, MA 02155
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$7,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$7,250
Total Monthly Price
$7,250
21 Emery St
21 Emery StMedford, MA 02155
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
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$5,500
Total Monthly Price8 Month Lease Term
5 Bedroom Apartment Available Oct 1Total Monthly Price
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$5,500
Total Monthly Price
$5,500
282 Boston Ave, Unit 2
282 Boston AveMedford, MA 02155
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$5,500
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5 Bedroom Apartment Available NowTotal Monthly Price
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$5,500
Total Monthly Price
$5,500
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$7,312
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$7,312
Total Monthly Price
$7,312
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$4,400
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5 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
60 Woods Ave, Unit 2
60 Woods AveSomerville, MA 02144
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$6,500
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5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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$4,000
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$4,000
Total Monthly Price
$4,000
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
24 Chetwynd Rd, Unit 2
24 Chetwynd RdSomerville, MA 02144
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$6,750
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,750
Total Monthly Price
$6,750
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$5,000
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5 Bedroom Apartment Available NowTotal Monthly Price
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$5,000
Total Monthly Price
$5,000
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
The 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.
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$6,500
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5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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$6,500
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5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
136 Burget Ave
136 Burget AveMedford, MA 02155
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
136 Burget Ave, Unit 1
136 Burget AveMedford, MA 02155
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,500
Total Monthly Price
$6,500
57 Quincy St
57 Quincy StMedford, MA 02155
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,250
Total Monthly Price
$6,250
14 Fairmount St, Unit 14.5
14 Fairmount StMedford, MA 02155
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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$5,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$5,500
Total Monthly Price
$5,500
123 Winthrop St, Unit 1
123 Winthrop StMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
215 Boston Ave
215 Boston AveMedford, MA 02155
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,250
Total Monthly Price
$6,250
14 Fairmount St, Unit 14.5
14 Fairmount StMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
190 North St, Unit 2
190 North StSomerville, MA 02144
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$6,250
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$6,250
Total Monthly Price
$6,250
14 Fairmount St, Unit 14.5
14 Fairmount StMedford, MA 02155
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$6,375
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,375
Total Monthly Price
$6,375
24 Chetwynd Rd
24 Chetwynd RdSomerville, MA 02144
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$6,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$6,500
Total Monthly Price
$6,500
185 Powder House Blvd, Unit 2
185 Powder House BlvdSomerville, MA 02144
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$4,950
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$4,950
Total Monthly Price
$4,950
65 Conwell Ave, Unit 1
65 Conwell AveSomerville, MA 02144
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$5,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$5,500
Total Monthly Price
$5,500
132 George St, Unit 2
132 George StMedford, MA 02155
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$6,200
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5 Bedroom Apartment Available NowTotal Monthly Price
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$6,200
Total Monthly Price
$6,200
3 Hamilton Rd, Unit 1
3 Hamilton RdSomerville, MA 02144
The Art of the Rental Viewing: What to look for during a property tour
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$7,031
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$7,031
Total Monthly Price
$7,031
76 Curtis St, Unit 1
76 Curtis StSomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$5,200
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$5,200
Total Monthly Price
$5,200
141 George St, Unit 1
141 George StMedford, MA 02155
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$7,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$7,000
Total Monthly Price
$7,000
43 Teele Ave, Unit 2
43 Teele AveSomerville, MA 02144
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$5,800
Plus Fees
5 Bedroom Apartments Available Jun 1, 2026132 George St
132 George StMedford, MA 02155
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$7,042
Plus Fees
5 Bedroom Apartments Available Jun 1, 202676 Curtis St
76 Curtis StSomerville, MA 02144
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$7,042
Plus Fees
5 Bedroom Apartments Available Jun 1, 202676 Curtis St
76 Curtis StSomerville, MA 02144
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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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 Studio Apartments | $2,270 | $1,550 | $2,914 |
| Winchester 1 Bedroom Apartments | $2,820 | $1,850 | $4,350 |
| Winchester 2 Bedroom Apartments | $3,234 | $2,000 | $5,128 |
| Winchester 3 Bedroom Apartments | $3,680 | $2,250 | $7,500 |
| Winchester 4 Bedroom Apartments | $4,660 | $3,200 | $6,066 |
| Winchester 5 Bedroom Apartments | $6,004 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,280 | $5,945 | $9,100 |
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
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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 106 Studio Apartments in Winchester with rent ranges from $1,550 to $2,914 with an average price of $2,270.
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 $1,850 to $4,350 with an average monthly rent of $2,820.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,000 to $5,128. Today's average rental price for Two Bedrooms here is $3,234.
How expensive are Winchester Three Bedroom Apartments?
There are currently 168 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,250 to $7,500 - averaging $3,680 for the location.
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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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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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.
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Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
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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.