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Apartments for Rent in Winchester Highlands

41 Rentals
.
  1. Building Photo - The Mave
    $400 Off
    Price Drop. $400 Off
    1 BED
    $2,465+
    2 BEDS
    $2,990+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,465 - $4,695
    Utilities & EssentialsVaries
    Total Monthly Price$2,465 - $4,695
         - 1 Month Lease

    The Mave

    225 Fallon Rd, Stoneham, MA 02180
    (978) 396-2160
  3. Building Photo - 3 Archer Dr
    3 BEDS, 3.5 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500
         - 12 Month Lease

    3 Archer Dr

    3 Archer Dr, Woburn, MA 01801
    Apply
  4. Building Photo - 10 Webster St
    4 BEDS, 2 BATHS
    $4,150
    Total Monthly Price Total Monthly Price New
    Base Rent$4,150
    Required Monthly FeesNone
    Total Monthly Price$4,150
         - 17 Month Lease

    10 Webster St Unit 1

    10 Webster St, Winchester, MA 01890
  5. 5 BEDS, 4 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500
         - 12 Month Lease

    9 Washington Ave

    9 Washington Ave, Woburn, MA 01801
  6. Building Photo - 378 Washington St
    5 BEDS, 4.5 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    378 Washington St

    378 Washington St, Winchester, MA 01890
  7. Building Photo - 415 Washington St
    2 BEDS, 1 BATH
    $2,700
    Total Monthly Price Total Monthly Price New
    Base Rent$2,700
    Required Monthly FeesNone
    Total Monthly Price$2,700

    415 Washington St Unit 1

    415 Washington St, Winchester, MA 01890
  8. 2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    36 Cross St Unit 1

    36 Cross St, Winchester, MA 01890
  9. 2 BEDS, 1.5 BATHS
    $2,900
    Total Monthly Price Total Monthly Price New
    Base Rent$2,900
    Required Monthly FeesNone
    Total Monthly Price$2,900

    224 Park St Unit C8

    224 Park St, Stoneham, MA 02180
  10. 3 BEDS, 3.5 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    3 Archer Dr

    3 Archer Dr, Woburn, MA 01801
  11. 3 BEDS, 1.5 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    20 Hancock St Unit 20

    20 Hancock St, Winchester, MA 01890
  12. 4 BEDS, 2 BATHS
    $4,150
    Total Monthly Price Total Monthly Price New
    Base Rent$4,150
    Required Monthly FeesNone
    Total Monthly Price$4,150

    10-12-12 Webster St Unit 1

    10-12-12 Webster St, Winchester, MA 01890
  13. Building Photo - 271 Washington St
    5 BEDS, 3 BATHS
    $7,000
    Total Monthly Price Total Monthly Price New
    Base Rent$7,000
    Required Monthly FeesNone
    Total Monthly Price$7,000

    271 Washington St

    271 Washington St, Winchester, MA 01890

Winchester at a Glance

Average Rent

N/A
(All bedrooms and property types)
0

School Rating

out of 10 Rating
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Schools in Winchester
5

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winchester
65

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Winchester

Winchester Highlands Neighborhood in Winchester, MA

If you’re looking for apartments in Winchester Highlands, Winchester, Apartment Finder has you covered! With great rent specials, price drops, and the best values in Winchester Highlands, one of these 13 rentals is sure to fit your list of apartment must-haves. Use our custom filters to narrow your search. Are you looking for a cozy studio apartment or a one-bedroom for yourself, a two-bedroom apartment for you and a roommate, or something more spacious with three-four beds? Apartment Finder has a wide variety of floorplans to meet every need.

Next, select the amenities you can't live without. Start with the basics and make sure your new place offers in-unit air conditioning, a washer and dryer, and a dishwasher. Then, take your living experience to the next level and look at apartments with a garage, swimming pool, and a gym. You can even combine amenties and ensure that your wheelchair accessible apartment has an elevator, or that your pet-friendly place has a balcony.

If filtering for amenities isn't specific enough, you can find apartments that fit your lifestyle when you search by specialty. Look at income-restricted apartments, senior living, short-term rentals, or student housing and find a place that caters to your exact needs. When you've found the perfect floorplan with all the essential amenities included, filter by price to make sure your new place fits your budget. Click on any of these properties to see photos and floor plans, read reviews, check out the rent calculator, and learn more about the neighborhood with information on nearby parks, shopping malls, and transit stops. With more than one million rentals currently available, Apartment Finder is the place to find your Winchester Highlands apartment.

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Average Rent in Nearby Cities

(For 1 bedroom apartments)

Getting Around Winchester

Transportation

44

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
65

Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
5

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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