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Winchester Highlands Homes for Rent

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  • /16

    $4,250 total monthly price

    • 4 Beds
    • 6 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    20 Lebanon St Unit 22, Winchester, MA 01890

    Convenient FURNISHED rental available for immediate occupancy in a great Winchester neighborhood. This well-maintained townhouse-style unit offers hardwood floors, four comfortable bedrooms, and 1.5 baths. The lower level includes in-unit laundry and plenty of storage—perfect for anyone seeking an easy, turnkey option while renovating or in transition. Enjoy two off-street parking spaces and a

    Agent Photo

    Catherine Albiani

    Better Homes and Gardens Real Estate - The Shanahan Group

    (781) 675-1642

    20 Lebanon St Unit 22, Winchester, MA 01890
  • /44

    $2,465 - $4,740 total monthly price

    The Mave

    1 - 2 Beds

    225 Fallon Rd, Stoneham, MA 02180

    Here, smart design imbues modern comforts with alfresco joys. Quartz countertops, glass-enclosed showers, and quality stainless steel appliances add to your quality of life. Energy-efficient windows stream in sunlight while wood-style flooring inspires your next jaunt outside. But with thoughtful features like our enhanced fitness center and cyber studio, you won't have to wander far to activate

    225 Fallon Rd, Stoneham, MA 02180
  • /18

    $2,700 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,305 Sq Ft
    • Apartment for Rent

    415 Washington St Unit 1, Winchester, MA 01890

    At 1300sqft, this unit far exceeds the average size for a 2 bed 1 bath. Priced competitively. Very close to 93 yet neatly tucked away, you'll have two side by side parking spaces on the side street (off the main road). Screened in backdoor area so you can be as close to comfort as possible. Once entering the space you'll be greeted by large bedrooms, a cozy kitchen and your choice of an

    Thomas Tsui Keller Williams Realty

    415 Washington St Unit 1, Winchester, MA 01890
  • /25

    $2,450 total monthly price

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    29 Harvard St Unit 1, Winchester, MA 01890

    Don’t miss this charming rental located in a desirable Winchester neighborhood! This unit features three spacious rooms and one full bathroom, offering comfortable and convenient living. Perfect for professionals or anyone seeking a quiet, well-situated home close to shops, dining, and public transportation. Pet friendly, recently updated with off street parking available. Kitchen boasts

    Prestige Homes Realty Team Prestige Homes Real Estate, LLC

    29 Harvard St Unit 1, Winchester, MA 01890
  • /16

    $3,000 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    36 Cross St Unit 1, Winchester, MA 01890

    Recently updated and bright first-floor unit featuring a spacious eat-in kitchen with new flooring, ample cabinet space, and bonus closet/pantry area. The kitchen also boasts an additional bonus room for your customization. This home offers two bedrooms, high ceilings, a renovated bathroom with a large shower, and beautiful hardwood floors. Enjoy the convenience of in-unit laundry and plenty of

    Dawn Felicani Gibson Sotheby's International Realty

    36 Cross St Unit 1, Winchester, MA 01890
  • /33

    $5,500 total monthly price

    • 5 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Apartment for Rent

    378 Washington St Unit 378, Winchester, MA 01890

    A rare find! Newer construction rental home/ attached single family/ featuring 5 bedrooms & 4 baths over 4 finished levels, close to Winchester center and Muraco Elementary School. This great home features large spacious rooms, a sunny granite kitchen w/ maple cabinets, hardwood floors/ open concept w/ family room & a gas fireplace w/ sliders that lead to a spacious deck overlooking a fenced in

    Kim Covino Compass

    378 Washington St Unit 378, Winchester, MA 01890
  • /34

    $11,000 total monthly price

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • House for Rent

    52 N Border Rd Unit 52, Winchester, MA 01890

    Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

    Dylan Archambault Archambault Real Estate

    52 N Border Rd Unit 52, Winchester, MA 01890
  • /41

    $7,500 total monthly price

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft
    • House for Rent

    211 Forest St, Winchester, MA 01890

    FURNISHED ONLY 1,2 or 3 MONTH WINTER RENTAL. If you’ve been thinking of a kitchen renovation or addition but dread the chaos of construction, or maybe you're visiting one of our world renowned hospitals, our stunning 5-bedroom, 3.5-bathroom, 3,500-square-foot home in the coveted Muraco school district is available for a 3-month winter rental (January through March) while my family snowbirds in

    Michael Gilbert Stuart St James, Inc.

    211 Forest St, Winchester, MA 01890

Why Live in Winchester Highlands

Winchester Highlands is a neighborhood known for its diverse and grand homes, ranging from late 19th-century builds to contemporary houses, featuring styles such as ranches, colonials, and two-family homes. The area is part of one of the best public school districts in the state, with highly rated institutions like Muraco Elementary, McCall Middle, and Winchester High School, all offering robust academic and extracurricular programs. The neighborhood is safer than the national average, providing a secure environment for residents. Outdoor enthusiasts will appreciate the proximity to the 2,200-acre Middlesex Fells Reservation, which features over 100 miles of trails, and the Tri-Community Greenway, a paved path for walking, jogging, and biking. Winchester Highlands also has local dining options like Eighty Eight Cafe and The Gingerbread Construction Co., with more restaurants and a Stop & Shop located in nearby Winchester Center. The neighborhood is well-connected, with the Massachusetts Bay Transportation Authority commuter rail at Winchester Center offering a roughly one-hour ride to Boston, and Interstate 93 providing a convenient 11-mile drive to the city. Additionally, Winchester Hospital, a 229-bed medical center, is located within the neighborhood. Residents can enjoy community events such as Winchester Town Day, which features a block party, street fair, and fireworks each June.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Winchester Highlands?
The most popular neighborhoods for renters near Winchester Highlands are Nobility Hill, Walnut Hill, The Flats, Downtown Woburn and Lindenwood.
What are the most popular zip codes for renters near Winchester Highlands?
The most popular zip codes for renters near Winchester Highlands are 01890, 02180, 01801, 02155 and 02176.
How to Rent a Home