Pricing ranges from
    $7,600 – 9,700/month

    Waterstone at the Circle

    385 Chestnut Hill Ave, Boston, MA 02135
    • Independent Living
    • Assisted Living

    Caring staff, great dining, amenities

    I've been very satisfied living here. The staff are warm, attentive and genuinely caring; maintenance and concierge respond quickly. Dining is restaurant-quality, the amenities (pool, gym, theater, library, lounges, craft and music rooms) are excellent, and the busy, resident-driven activities and sunny apartments in a great Cleveland Circle/Boston location make it a welcoming, upscale independent-living community I happily recommend.

    Current/former resident
    Sep 2026

    Pricing

    Prices shown are estimates and subject to change. Contact your senior living advisor for current pricing.

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    Amenities

    Healthcare services

    • Assistance with dressing
    • Coordination with health care providers
    • Hospice waiver
    • Medication management
    • Mental wellness program

    Healthcare staffing

    • 12-16 hour nursing
    • 24-hour call system

    Meals and dining

    • Meal preparation and service
    • Restaurant-style dining

    Room

    • Air-conditioning
    • Cable
    • Fully furnished
    • Housekeeping and linen services
    • Internet
    • Kitchenettes
    • Private bathrooms
    • Telephone
    • Wifi

    Transportation

    • Community operated transportation
    • Transportation arrangement
    • Transportation arrangement (non-medical)
    • Transportation to doctors appointments

    Common areas

    • Beauty salon
    • Cafe
    • Computer center
    • Dining room
    • Family private dining rooms
    • Fitness room
    • Gaming room
    • Garden
    • Outdoor patio
    • Outdoor space
    • Pet friendly
    • Small library
    • Wellness center

    Community services

    • Concierge services
    • Fitness programs
    • Move-in coordination
    • Swimming pool

    Activities

    • Community-sponsored activities
    • Continuing learning programs
    • Planned day trips
    • Resident-run activities
    • Scheduled daily activities

    Reviews

    4.49·(57)

    Overall rating

    1. 5
    2. 4
    3. 3
    4. 2
    5. 1
    • Care

      4.5
    • Staff

      4.6
    • Meals

      4.6
    • Amenities

      5.0
    • Value

      4.0

    Pros

    • attentive, friendly and welcoming staff
    • responsive maintenance and meticulous housekeeping
    • chef-driven, high-quality dining with heart-healthy options
    • robust life-enrichment and cultural programming
    • resident-led social groups and intellectual clubs
    • extensive on-site amenities (pool, gym, theater, library, craft room)
    • convenient urban location with transit access and city views
    • scheduled transportation service for appointments and outings
    • well-designed, sunlit apartments with boutique feel
    • strong hospice and end-of-life support
    • active, social independent-living environment

    Cons

    • variable clinical support for residents with increasing care needs
    • occasional sanitation concerns in food-service delivery
    • language and communication barriers among some dining staff
    • inconsistent management organization and communication
    • price-to-value and affordability concerns
    • resident-mix and cognitive-acuity mismatch affecting social expectations

    Summary of reviews

    Waterstone at the Circle is consistently described as a polished, amenity-rich independent living community with a strong emphasis on social programming and high-quality dining. Reviewers praise the facility's downtown-adjacent location, boutique-style apartments with ample natural light, and an extensive set of shared spaces — indoor pool, exercise rooms, theater, library, craft room, and multiple dining venues — that support an active social life. Many residents and family members highlight the convenience of shuttle/ride services for medical and social appointments and the proximity to cultural resources in Boston.

    Staff and care receive frequent positive mention: front-desk and concierge personnel are characterized as warm and helpful, maintenance responses are described as rapid, and housekeeping is noted for being friendly and thorough. The community also receives credit for compassionate hospice and end-of-life support and for fostering a welcoming, family-like atmosphere. At the same time, reviewers indicate a pattern-level concern about the community's suitability for people whose care needs are progressing beyond independent living. Several comments reflect that clinical support and staffing levels may be inconsistent for residents requiring more intensive assistance, and that the resident mix sometimes includes individuals with significant memory impairment whose behaviors can affect the independent-living social environment.

    Dining and programming are central strengths. The dining program is widely described as chef-driven with sophisticated menus and heart-healthy, low-sodium options; reviewers note both fine-dining experiences and casual bistro offerings. Life-enrichment is active and diverse: lectures, concerts, writing groups, men's discussion groups, book and movie clubs, card and board games, and resident-initiated activities are common. That said, there are isolated operational issues connected to food service — characterized as sanitation lapses and occasional service-staff communication challenges — that suggest opportunities for tighter quality control and staff training in dining operations.

    Facility operations and management present a mixed picture. Many reviews emphasize professional, attentive staff and a smoothly managed move-in transition, while others describe disorganization, inconsistent communication from management, or front-office shortcomings. Affordability and value-for-cost are recurrent themes: some families view the community as expensive but worth the amenities and service, whereas others feel the price point is not justified by the experience. Prospective residents should also consider community fit: those seeking an intellectually engaged, resident-led independent-living environment report high satisfaction, while those expecting a strictly homogeneous low-acuity population may experience mismatches due to the presence of higher-acuity residents.

    Overall, Waterstone at the Circle is well suited to independent seniors who prioritize social programming, high-quality dining, and a comprehensive amenity package in an urban location. Prospective residents and families should assess current clinical supports and management responsiveness relative to changing care needs, inquire about dining quality-control practices and staff language/communication training, and consider financial expectations to determine whether the community aligns with their clinical and lifestyle priorities.

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    Location

    Map showing location of Waterstone at the Circle

    Waterstone at the Circle is located at 385 Chestnut Hill Ave, Boston, MA, 02135.

    About Waterstone at the Circle

    Waterstone at the Circle sits in the Cleveland Circle neighborhood of Boston, right by Cassidy Park and Chestnut Hill Reservoir, giving people scenic views and quick access to parks and walking trails, and you can see right away that they made sure the location is pretty convenient since two MBTA Green Line stops are close by, making trips to downtown Boston and local cultural spots simple. The building is multi-level and holds bright, private apartments, including one and two-bedroom layouts, offering roomy closets, designer kitchens, in-unit laundry, and options for private outdoor space, and you'll also find everyday conveniences like Wi-Fi, cable TV, and individual controls for heat and air, which really helps folks settle in. The community design includes classic details from the old Circle Cinema, and there are lots of shared places like lounges, a library, art and card rooms, movie theaters, and entertainment venues inside, so there's always somewhere to go for quiet time or social events, plus you get things like a computer room, prayer space, and mailboxes, while outside you can use the patios, tennis courts, gardens, enclosed areas, and enjoy water features for relaxing or meeting up with friends.

    People living at Waterstone at the Circle get to join a wide-ranging activity program with daily fitness, arts and crafts, musical performances, learning classes, movie nights, city outings, holiday events, creative art workshops, and volunteer opportunities, and the indoor heated pool, well-equipped fitness center, spa, and wellness center give everyone options for both movement and rest, including special programs like aquatic fitness, yoga, and Tai Chi. There's a chic main dining hall serving gourmet meals with locally sourced, seasonal menus, flexible dining times, and accommodations for kosher, low salt, vegetarian diets, along with room service and guest meals, so you can eat in the way that suits you best, and the chef prepares meals with attention to taste and health, which some really appreciate. Waterstone provides all sorts of transport and shopping services, from private car service to medical appointments or errands, with several parking choices, including underground and guest parking, and the security setup includes emergency response systems, security staff, and regular safety checks.

    As a pet-friendly community, pets are welcome, and there's a calm pace with interesting neighbors, organized support for residents and their pets, and a sense of friendliness. The community welcomes adults age 62 and up and offers several care levels-so you'll find independent living, assisted living, memory care for adults with Alzheimer's or dementia, skilled nursing, respite care, in-home health care, and even hospice support, all on one urban campus run by Epoch. There's on-site medical monitoring, medication management, cognitive learning centers, diabetes and incontinence support, and a clinical liaison to help coordinate health care-some services are available 12 to 16 hours a day with a full 24-hour call system for emergencies, plus telehealth through Tembo Health for quick check-ins. The memory care program provides specialized, safe settings, and assisted living services include personal help with daily needs, planned activities, and dedicated staff always nearby, while independent living allows for a more hands-off lifestyle for those who prefer that.

    Flexible visitation hours let family and friends visit easily, and overnight guest rooms are ready for visitors, so nobody feels left out if a loved one wants to stay over, and planning resources, cost guidance, and care glossaries are available for guidance about payments or future needs, with information about Medicare, Medicaid, veterans benefits, insurance, tax options, and house sales. Residents can shop at the on-site market, use the salon, attend business or church services, and have their newspapers delivered right to their door. There are systems supporting wheelchair access and non-ambulatory care, plus secure entry, making daily life smoother for people with mobility needs. The whole place is set up for folks who want an active, urban lifestyle but still want comfort, safety, and a schedule that fits their interests, so you can take in the vibrant neighborhood or stay in for art, fitness, music, and good meals.

    Waterstone at the Circle tries to balance an easy-going, elegant way of living with dependable support, and different services match changing health or social needs, all in one place with apartment homes overlooking beautiful Boston scenes. This community holds an average review score of 8.4 out of 10 from many residents and families, reflecting solid satisfaction with both care and amenities.

    People often ask...

    Waterstone at the Circle offers competitive pricing, with rates starting at a cost of $7,600 per month.

    Waterstone at the Circle offers independent living and assisted living.

    There are 34 photos of Waterstone at the Circle on Mirador.

    The full address for this community is 385 Chestnut Hill Ave, Boston, MA 02135.

    No, Waterstone at the Circle does not offer respite care. Respite care in assisted living communities provides temporary, short-term relief for primary caregivers by offering professional care for their loved ones. It allows individuals to stay in an assisted living community for a limited time, giving caregivers a break while ensuring residents receive necessary support and assistance with daily activities.

    Disclaimer

    Mirador Living is not affiliated with the owner or operator(s) of Waterstone at the Circle. The information above has not been verified or approved by the owner or operator. For exact information, please contact Waterstone at the Circle directly. There is no cost for this service. We are compensated by the community you select.

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