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West Side Homes for Rent

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    $3,220 - $3,800 per month

    Sanctuary Winchester West

    Studio-3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

    416 Cambridge St, Winchester, MA 01890
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    $9,250 per month

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    35 Thornberry Rd, Winchester, MA 01890

    Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half bathrooms,

    Frank Celeste Gibson Sotheby's International Realty

    35 Thornberry Rd, Winchester, MA 01890
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    $6,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft
    • House for Rent

    3 Wainwright Rd Unit SFAM, Winchester, MA 01890

    Explore Sanctuary West's one-of-a-kind 1,836 square foot single family home! This 3-bedroom, 2.5 bathroom standalone home features luxury finishes with added historical touches such as exposed wood beams.

    Christine Ferris Ideal Real Estate Services, Inc.

    3 Wainwright Rd Unit SFAM, Winchester, MA 01890
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    $9,400 per month

    • 5 Beds
    • 4.5 Baths
    • 5,016 Sq Ft
    • House for Rent

    22 Amberwood Dr, Winchester, MA 01890

    Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador

    Anita Lin Coldwell Banker Realty - Lexington

    22 Amberwood Dr, Winchester, MA 01890
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    $15,000 per month

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft
    • House for Rent

    20 Amberwood Dr, Winchester, MA 01890

    Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

    Dan Li Keller Williams Realty

    20 Amberwood Dr, Winchester, MA 01890
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    $7,450 per month

    • 4 Beds
    • 4 Baths
    • 4,650 Sq Ft
    • House for Rent

    31 Coolidge Rd, Winchester, MA 01890

    Available now! Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neighborhood with easy commute to schools, Boston, highways and MBTA train stations. The 1st floor offers a foyer with formal dining room and living room in either sides. The kitchen, with island and full breakfast/dining area, flows into a family room that transitions to a private

    Carlos Xu Lexwin Realty

    31 Coolidge Rd, Winchester, MA 01890

Why Live in West Side

The West Side neighborhood in Winchester offers a blend of early- to mid-20th-century architecture, with homes ranging from 1920s and 1930s Colonials to midcentury Cape Cods, ranch-styles, split-levels, and more recent Modern Traditional builds from 2015 to 2024. Two-unit townhouses are also present on the south side. The area is characterized by large front and back lawns, wooded lots, and winding suburban streets without sidewalks. Residents enjoy proximity to natural features like Mount Pisgah and Whipple Hill, which offer hiking trails and off-leash areas for dogs. The Winchester Country Club provides an 18-hole golf course, while Upper Mystic Lake is a spot for fishing. The Minuteman Commuter Bikeway offers a flat, 9-mile trail for cyclists. Essential shopping is accessible with Whole Foods 3 miles away, and Market Basket and H-Mart 4 miles north in Burlington. The Burlington Mall, less than 5 miles away, features over 185 retailers and restaurants. Downtown Winchester is known for its boutiques and dining options. Community events, such as Spirit Weekend and activities at the Arthur Griffin Photography Museum, foster a strong local spirit. Route 3 and Interstate 95 provide connectivity, with Wedgemere train station offering a 20-minute ride to Boston's North Station. Logan International Airport is about 14 miles southeast. The neighborhood is served by highly rated schools, including Vinson-Owen Elementary, McCall Middle, Winchester High, and Lexington Christian Academy. The crime rate in the area is lower than the national average, contributing to a sense of security for residents.

Frequently Asked Questions

What are the most popular neighborhoods for renters near West Side?
The most popular neighborhoods for renters near West Side are Shakerhill, Arlington Heights, The Flats, North Main and Countryside.
What are the most popular zip codes for renters near West Side?
The most popular zip codes for renters near West Side are 01890, 01801, 02474, 02420 and 02476.
How to Rent a Home