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Rent Specials
$2,256 - $9,297
Plus Fees
Studio to 3 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
Luxury Apartments for Rent in Winchester, MA (420 Rentals)
The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.
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$2,695
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,695
Total Monthly Price
$2,695
6 Skillings Rd, Unit #2-J
6 Skillings RdWinchester, MA 01890
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$2,695
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,695
Total Monthly Price
$2,695
6 Skillings Rd, Unit 2
6 Skillings RdWinchester, MA 01890
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Rent Specials
$3,275 - $7,356
Plus Fees
1 to 3 Bedroom Apartments Available NowSanctuary Winchester North
25-35 River StWinchester, MA 01890
343 Washington St
WinchesterMA01890
35 Vine 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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Rent Specials
$1,800 - $3,200
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowStonehill Towers
5 Stonehill DrStoneham, MA 02180
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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$2,252 - $4,925
Total Monthly Price12 Month Lease Term
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,252 - $4,925
Total Monthly Price
$2,252 - $4,925
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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Rent Specials
$2,290 - $5,618
Plus Fees
Studio to 3 Bedroom Apartments Available NowThe Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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$2,295 - $3,295
Plus Fees
1 to 2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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Rent Specials
$2,350 - $2,500
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available Oct 15GlenBrook Estates
200 Bedford RdWoburn, 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
$2,431 - $5,357
Plus Fees
Studio to 3 Bedroom Apartments Available NowHanover Stoneham
95 Maple StStoneham, MA 02180
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$2,496 - $3,746
Plus Fees
Studio to 2 Bedroom Apartments Available NowBrigham Square Apartments
30 Mill StArlington, MA 02476
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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$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
153 W Adams St, Unit 2
153 W Adams StSomerville, MA 02144
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$2,505 - $3,497
Plus Fees
1 to 2 Bedroom Apartments Available NowWashington Crossing Apartments
55 Cedar StWoburn, MA 01801
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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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$2,600
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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$2,600
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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$2,600
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1
69 Raymond AveSomerville, 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 Jun 1, 2026Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
37 Pearl St, Unit 1st floor apt near Tufts
37 Pearl StMedford, MA 02155
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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
60 Hamilton St
60 Hamilton StMedford, MA 02155
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$2,650
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,650
Total Monthly Price
$2,650
80 Orchard St, Unit Apt 1
80 Orchard StMedford, MA 02155
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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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$2,699
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,699
Total Monthly Price
$2,699
34 Park Avenue Ext, Unit 34
34 Park Avenue ExtArlington, MA 02474
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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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 15Total Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
1 Boline Pl, Unit 1 Boline Place
1 Boline PlWoburn, MA 01801
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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
28 Rawson Rd, Unit 1
28 Rawson RdArlington, MA 02474
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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
60 Hamilton St, Unit 1
60 Hamilton 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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$2,745 - $5,050
Total Monthly Price1 Month Lease Term
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,745 - $5,050
Total Monthly Price
$2,745 - $5,050
The Mave
225 Fallon RdStoneham, MA 02180
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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
67 Greenleaf Ave, Unit 1
67 Greenleaf AveMedford, MA 02155
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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
42 Summer St, Unit 42 Summer Street
42 Summer StMedford, MA 02155
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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
53 Oakland St
53 Oakland StMedford, MA 02155
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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
33 Irvington Rd
33 Irvington RdSomerville, MA 02144
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
110 W Quincy St, Unit 1
110 W Quincy StSomerville, 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.
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$2,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Sep 15Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
53 Fairfax St, Unit 2
53 Fairfax StSomerville, MA 02144
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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
110 W Quincy St, Unit #1
110 W Quincy StSomerville, MA 02144
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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
109 Westmoreland Ave, Unit 109 Westmoreland Ave
109 Westmoreland AveArlington, MA 02474
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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
110 W Quincy St, Unit 2
110 W Quincy StSomerville, MA 02144
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
8 Usher Rd, Unit 1
8 Usher RdMedford, MA 02155
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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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$2,875
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,875
Total Monthly Price
$2,875
15 Pond Ln, Unit #26
15 Pond LnArlington, MA 02474
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
8 Madison St, Unit 1
8 Madison StMedford, MA 02155
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, 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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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
69 Raymond Ave, Unit 1R
69 Raymond 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 | $2,271 | $1,550 | $2,914 |
| Winchester Luxury 1 Bedroom Apartments | $2,815 | $1,850 | $4,350 |
| Winchester Luxury 2 Bedroom Apartments | $3,234 | $2,195 | $5,128 |
| Winchester Luxury 3 Bedroom Apartments | $3,701 | $2,250 | $7,500 |
| Winchester Luxury 4 Bedroom Apartments | $4,654 | $3,200 | $6,066 |
| Winchester 5 Bedroom Apartments | $5,988 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,262 | $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
- Winchester Neighborhoods
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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 106 Studio Apartments in Winchester with rent ranges from $1,550 to $2,914 with an average price of $2,271.
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 $2,815.
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 $5,128. 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 $3,701 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.
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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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
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.