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$4,500
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4 Bedroom Apartments Available NowBrightly Renovated 4-Bed / 2-Bath • 1,800 sq
86 Orchard StMedford, MA 02155
4 Bedroom Luxury Apartments for Rent in Winchester, MA (54 Rentals)
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available May 31, 2026Total Monthly Price
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$4,200
Total Monthly Price
$4,200
100 W Adams St, Unit 2
100 W Adams StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Nov 15Total Monthly Price
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$4,500
Total Monthly Price
$4,500
14 Quincy St
14 Quincy StMedford, MA 02155
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$4,400
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
11 Garfield Ave, Unit 1
11 Garfield AveWoburn, MA 01801
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$8,000
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4 Bedroom Apartment Available NowTotal Monthly Price
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$8,000
Total Monthly Price
$8,000
19 Shirley Rd, Unit 19
19 Shirley RdMedford, MA 02155
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$3,300
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4 Bedroom Apartment Available NowTotal Monthly Price
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$3,300
Total Monthly Price
$3,300
167 Sharon St
167 Sharon StMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,400
Total Monthly Price
$4,400
100 W Adams St, Unit 100
100 W Adams StSomerville, MA 02144
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,200
Total Monthly Price
$4,200
102 W Adams St, Unit 2
102 W Adams StSomerville, MA 02144
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$4,200
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2T
62 Woods AveSomerville, MA 02144
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$4,000
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,800
Total Monthly Price
$4,800
112 College Ave, Unit U2
112 College AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
102 W Adams St, Unit 2
102 W Adams StSomerville, MA 02144
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$5,600
Total Monthly Price24 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,600
Total Monthly Price
$5,600
19 Sunset Rd, Unit 1
19 Sunset RdSomerville, MA 02144
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$5,550
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,550
Total Monthly Price
$5,550
24 Chetwynd Rd, Unit 1
24 Chetwynd RdSomerville, MA 02144
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$4,300
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,200
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2A
62 Woods AveSomerville, MA 02144
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$4,200
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4 Bedroom Apartment Available Dec 1Total Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,650
Total Monthly Price
$4,650
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$5,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,650
Total Monthly Price
$5,650
86 Quincy St, Unit 2
86 Quincy StMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
67 Greenleaf Ave, Unit 1
67 Greenleaf AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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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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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Dec 1Total Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$4,400
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,400
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit #2
82 Quincy StMedford, MA 02155
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$4,600
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
50 Curtis Ave, Unit 1
50 Curtis AveSomerville, MA 02144
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$5,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,000
Total Monthly Price
$5,000
100 W Adams St, Unit 2
100 W Adams StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$4,000
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, 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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$4,000
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$4,000
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$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$5,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,800
Total Monthly Price
$5,800
303 Boston Ave, Unit 3
303 Boston AveMedford, MA 02155
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$4,600
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
14 Barton St, Unit 2
14 Barton StSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,400
Total Monthly Price
$4,400
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,800
Total Monthly Price
$4,800
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, MA 02155
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$4,900
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,900
Total Monthly Price
$4,900
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$5,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$5,000
Total Monthly Price
$5,000
104 W Adams St, Unit 2
104 W Adams StSomerville, MA 02144
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$3,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
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$3,900
Total Monthly Price
$3,900
56 Gordon St, Unit 1
56 Gordon StSomerville, MA 02144
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$3,700
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,700
Total Monthly Price
$3,700
248 Powder House Blvd, Unit B
248 Powder House BlvdSomerville, MA 02144
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
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$3,700
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026248 Powder House Blvd
248 Powder House BlvdSomerville, MA 02144
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$4,000
Plus Fees
4 Bedroom Apartments Available Jun 1, 202614.5 Fairmount St
14.5 Fairmount StMedford, MA 02155
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$4,400
Plus Fees
4 Bedroom Apartments Available Jun 1, 202656 Gordon St
56 Gordon StSomerville, MA 02144
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$4,750
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026288 Boston Ave
288 Boston AveMedford, MA 02155
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$5,600
Plus Fees
4 Bedroom Apartments Available Jun 1, 202650 Upland Rd
50 Upland RdSomerville, MA 02144
The Art of the Rental Viewing: What to look for during a property tour
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.
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 | $2,156 | $1,200 | $2,829 |
| Winchester 1 Bedroom Apartments | $2,662 | $1,395 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,222 | $2,195 | $5,500 |
| Winchester 3 Bedroom Apartments | $3,664 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,487 | $3,000 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,161 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,089 | $5,945 | $8,450 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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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.
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
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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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
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 104 Studio Apartments in Winchester with rent ranges from $1,200 to $2,829 with an average price of $2,156.
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 $1,395 to $4,195 with an average monthly rent of $2,662.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,195 to $5,500. Today's average rental price for Two Bedrooms here is $3,222.
How expensive are Winchester Three Bedroom Apartments?
There are currently 155 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,664 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.
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.
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.