The Gables at Winchester

299 Cambridge Street, Winchester, MA 01890
Assisted Living · Independent Living

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For residents and staff
(781) 756-1026
For pricing and availability
(781) 462-6704

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Last updated Dec 24, 2025

About The Gables at Winchester

The Gables at Winchester is an Assisted Living community in the Winchester area that also offers Independent Living care. Costs for this community start at $5,545/mo, which is lower than the cost of care in the Winchester area of $5,850/mo.

Nestled amidst the picturesque New England pines, The Gables at Winchester offers a welcoming and vibrant atmosphere for seniors seeking a fulfilling lifestyle. This community is renowned for its commitment to providing exceptional care and medical services, ensuring that residents receive the support they need with compassion and expertise. With a dedicated team that has been part of the community for decades, residents can enjoy peace of mind knowing that help is always available, allowing them to focus on what truly brings them joy. The Gables at Winchester is not just about excellent care; it's a place where residents can thrive and explore a variety of engaging activities. From participating in the gardening club to enjoying movie nights in the community theater, there's always something to do. The Lifestyle360 program offers a range of activities, group trips, and clubs that foster social connections and personal growth. For those who love the outdoors, the community's park-like grounds and walking paths provide the perfect setting for a leisurely stroll or a moment of reflection. Located in a neighborhood that combines the tranquility of nature with the convenience of urban amenities, The Gables at Winchester is surrounded by a wealth of options for dining, shopping, and healthcare. Residents have easy access to nearby physicians at Harvard Vanguard Medical Associates and can fill prescriptions at the local Walgreens pharmacy. For leisurely outings, the Burlington Mall and the charming Winchester Center offer a variety of shops and cafes, while the Woburn Country Club and Symphony Hall provide opportunities for recreation and entertainment. Dining at The Gables at Winchester is a delightful experience, with a focus on nutrition and flavor. Residents can savor classic New England dishes made from scratch, with ingredients sourced fresh from local providers. The culinary team is dedicated to accommodating dietary preferences and restrictions, ensuring that each meal is both delicious and healthful. Whether enjoying a meal in the restaurant-style dining rooms or catching up with friends at the Black Horse Café, dining here is always a pleasure. With its exceptional care, vibrant lifestyle, and prime location, The Gables at Winchester stands as a beacon of warmth and community for seniors seeking a place to call home.


AI-generated description based on Seniorly's proprietary data. Contact a Seniorly representative to learn more.

About Sinceri Senior Living

Average Rating
3.5
(49 reviews)

The Gables at Winchester is a member of the Sinceri Senior Living portfolio of communities. Sinceri Senior Living is led by CEO Chris Belford, a veteran with over 15 years in senior living and the 2023 recipient of the McKnight's Senior Living Pinnacle Award. Founded in 1988, with 38 years of experience, Sinceri operates 139 communities in 21 states. Rooted in a mission to honor the aging process, the family-founded organization has earned recognition as a Great Place to Work and Forbes America's Best Midsize Employer. Committed to exceptional care and service, Sinceri simplifies the process of finding senior living, ensuring it is easy and stress-free for seniors and their families. Sinceri Senior Living communities have an average rating of 3.5 out of 5 stars on Seniorly.

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Pricing for The Gables at Winchester

Pricing starts from
$5,545/mo
One BedroomFrom $5,545/mo

Your monthly costs at The Gables at Winchester will vary depending on room type and the level of care needed. Click the button above to connect with your Seniorly Local Advisor for more accurate pricing.

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Reviews for The Gables at Winchester

9.8
Seniorly Community Score
Based on Seniorly's proprietary scoring, including 63 reviews across the web.

What families are saying

We’ve gathered and summarized real family reviews from across the internet for you. Contact a Seniorly representative for details.
The Gables at Winchester is a senior living community that receives high praise for its welcoming atmosphere, compassionate staff, and comprehensive services. Many reviewers highlight the staff's dedication, noting their kindness, professionalism, and attentiveness, which help residents feel at home and supported. The facility is described as clean, bright, and cheerful, with a variety of activities and social opportunities that keep residents engaged and happy. The dining experience is generally well-received, with some residents appreciating the quality and variety of meals, although a few mention the food could be more varied and flavorful. The community offers a balance of independence and assistance, with services like transportation, housekeeping, and medical care readily available. The Gables is noted for its spacious and well-maintained apartments, though some reviewers express a desire for more outdoor walking areas. The facility's location near Boston is appreciated for its convenience and access to cultural outings. While most feedback is positive, a few reviews mention concerns about temperature control in rooms and the treatment of staff. Despite these issues, the overall sentiment is that The Gables provides a nurturing and enriching environment for seniors, making it a highly recommended choice for those seeking assisted living. The community's ability to foster connections among residents and staff is frequently highlighted, contributing to a sense of belonging and family.
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Care offered at The Gables at Winchester

Care services

  • Medication management
  • Assistance with bathing
  • 24-hour supervision

Amenities at The Gables at Winchester

  • Furnished
  • Emergency Alert System
  • Transportation & parking
  • Move-in coordination
  • Concierge
  • Meal preparation and service
  • Community-sponsored activities
    Bridge club, Book club, Choir / singing club, Bible study group, Current events club, Cards / pinochle club, Quilting or sewing club, Happy hour, Cooking classes, Live dance or theater performances, Holiday parties, Dances, Art classes, Has karaoke, Trivia games, Live well programs, Has birthday parties, Wine tasting, Walking club, Has wii bowling, Has garden club
  • Pet-friendly
    Dogs, Cats
  • Faith Based
    Christian services, Protestant services, Jewish services, Catholic services, Devotional activities on site, Devotional activities offsite
  • Special dietary restrictions
    Pureed meals, Low / No Sodium

Ask a local senior living advisor a question

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Jane DiSalle
Jane DiSalle
Winchester Seniorly Advisor
  • 5 (8 reviews)
  • Families helped: 9063
  • 17 years of experience
  • Top advisor: 2024, 2025
  • Need help sooner?
    Call us at (781) 462-6704

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    Seniorly Neighborhood Insights for Winchester, MA (01890)

    Discover crucial neighborhood insights from reputable sources like census.gov and epa.gov. Remember, this data offers a general overview of the area and might not reflect the area immediately surrounding the property.

    Total population: 872

    47% of population is 50+ years old, 27% is 65+ years old
    The poverty rate is 13% higher for this region compared to the Massachusetts state average, which is 9%

    Diversity

    80% of population identify themselves as Black, 0% as Asian, 0% as Hispanic, and 20% as White

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