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$3,900
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
89 Hillsdale Rd, Unit 1
89 Hillsdale RdMedford, MA 02155
Luxury Apartments for Rent in Winchester, MA (332 Rentals) Page 4 of 7
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
54 Upland Rd, Unit 2
54 Upland RdSomerville, MA 02144
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
54 Upland Rd, Unit 2
54 Upland RdSomerville, MA 02144
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$3,999
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,999
Total Monthly Price
$3,999
8 Greenleaf Ave, Unit 8 Greenleaf Ave Medford
8 Greenleaf AveMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,000
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
119 Burget Ave, Unit 2
119 Burget AveMedford, MA 02155
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
117 Burget Ave, Unit 1
117 Burget AveMedford, MA 02155
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
117 Burget Ave
117 Burget AveMedford, MA 02155
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$4,050
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,050
Total Monthly Price
$4,050
117 Burget Ave, Unit 1
117 Burget AveMedford, MA 02155
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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
290 Boston Ave, Unit 1
290 Boston AveMedford, MA 02155
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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
117 Hillsdale Rd, Unit 1
117 Hillsdale RdSomerville, MA 02144
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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
106 W Adams St, Unit 1st floor
106 W Adams StSomerville, MA 02144
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$4,150
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,150
Total Monthly Price
$4,150
38 George St, Unit 1
38 George StMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2A
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
Base Rent
$4,200
Total Monthly Price
$4,200
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 Nov 1Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2T
62 Woods AveSomerville, MA 02144
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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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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
86 Orchard St, Unit 3
86 Orchard StMedford, 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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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
119 Burget Ave
119 Burget AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
119 Burget Ave, Unit #2
119 Burget AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,300
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,300
Total Monthly Price
$4,300
190 North St, Unit 2
190 North StSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
11 Garfield Ave, Unit 1
11 Garfield AveWoburn, MA 01801
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
100 W Adams St, Unit 100
100 W Adams StSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
117 Burget Ave, Unit 1
117 Burget AveMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
215 Boston Ave
215 Boston AveMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$4,500
Plus Fees
4 Bedroom Apartments Available Nov 1Brightly Renovated 4-Bed / 2-Bath • 1,800 sq
86 Orchard StMedford, MA 02155
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Nov 15Total Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
14 Quincy St
14 Quincy StMedford, MA 02155
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit #2
82 Quincy StMedford, MA 02155
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
14 Barton St, Unit 2
14 Barton StSomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,600
Total Monthly Price
$4,600
50 Curtis Ave, Unit 1
50 Curtis 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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$4,750
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,750
Total Monthly Price
$4,750
2 Osgood St, Unit 1
2 Osgood StSomerville, MA 02143
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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
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, 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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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
112 College Ave, Unit U2
112 College AveMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$4,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,900
Total Monthly Price
$4,900
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$4,950
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,950
Total Monthly Price
$4,950
65 Conwell Ave, Unit 1
65 Conwell AveSomerville, MA 02144
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 | $2,166 | $1,200 | $2,829 |
| Winchester Luxury 1 Bedroom Apartments | $2,669 | $1,395 | $4,195 |
| Winchester Luxury 2 Bedroom Apartments | $3,230 | $2,195 | $5,999 |
| Winchester Luxury 3 Bedroom Apartments | $3,682 | $2,500 | $6,900 |
| Winchester Luxury 4 Bedroom Apartments | $4,567 | $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.
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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 104 Studio Apartments in Winchester with rent ranges from $1,200 to $2,829 with an average price of $2,166.
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 $2,669.
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 $5,999. Today's average rental price for Two Bedrooms here is $3,230.
How expensive are Winchester Three Bedroom Apartments?
There are currently 151 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,900 - averaging $3,682 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.