Explore Open Rooms

1 Contact details
2 What type of senior care service are you looking for?
3 What budget do you have in mind for senior care?
4 How soon do you need to find care?
5 Additional details

Thank you for your interest!

Our team will be in touch shortly to help with next steps.

Assisted Living Home

The Gables at Winchester

Assisted Living Home

The Gables at Winchester

299 Cambridge St, Winchester, MA 01890 View map
Overview of The Gables at Winchester

The Gables at Winchester is one of the trusted assisted senior living communities in the city– offering assisted living, memory care, and skilled nursing. They understand that an enriching senior living experience begins with the right lifestyle that reinvents the meaning of senior care. The home-like community enriches and encourages all residents to still live freely on their own terms while receiving the necessary support. The Gables is a home that honors your trust in them; they ensure that seniors are given the utmost level of care and respect.

The vibrant home offers a list of services that include 24-hour nursing supervision, transportation, housekeeping, medication management, an emergency call response system in every room, and cozy outdoor and indoor common areas. Other activities include movie nights, fitness classes, and other scheduled social events.

(781) 756-1026

Capacity and availability

Medium-capacity home

Offers a balance of services and community atmosphere.

Total beds 123
Bed community size
123-bed community
A larger shared setting that may offer more common spaces and organized community services.
Years in operation
35 years in operation
A longer operating history, which may indicate experience navigating regulations and delivering ongoing care.
Walk Score
Walk Score: 52 / 100
Moderately walkable. Some errands can be accomplished on foot, with a mix of nearby amenities.

Additional licensing details

Year opened: 1996

Ownership & operating entity

Nonprofit ownership: No

Type Of Units

Traditional
123 units
Total beds
123 units

Staffing

Key information about the people who lead and staff this community.

Leadership

Contact: Ms. Evelyn Callahan, Executive Director

Contact Information

Fax: (781) 756-0636
Business Hours: Monday - Friday 9:00 AM - 5:00 PM

Additional Policies & Features

Continuing Care Retirement Community (CCRC)

What does this home offer?

Pets allowed icon
Pets allowed icon

Pets Allowed: Yes, Pets Allowed

Housing options icon
Housing options icon

Housing Options: Studio / 1 Bed / 2 Bed

Building type icon
Building type icon

Building Type: 3-story

Dining services icon
Dining services icon

Dining Services

Beauty services icon
Beauty services icon

Beauty Services

Transportation services icon
Transportation services icon

Transportation Services

Housekeeping icon
Housekeeping icon

Housekeeping Services

Recreational activities icon
Recreational activities icon

Recreational Activities

Exercise program icon
Exercise program icon

Exercise Programs

Types of Care at The Gables at Winchester

Assisted Living Independent Living Respite Care
Contact The Gables at Winchester

Compare Assisted Living around Winchester The information below is reported by the Massachusetts Executive Office of Elder Affairs and Department of Public Health.

The Gables at Winchester
AL

Assisted Living A licensed, long-term care setting for seniors or individuals with disabilities who need help with daily activities — like bathing, dressing, and medication management — but not 24-hour skilled nursing. Offers housing, meals, and around-the-clock support while aiming to maximize resident independence.

IL

Independent Living Lifestyle-focused communities for older adults offering dining, activities, and transportation with minimal personal care. Best for active, independent seniors who want community without medical support.

RC

Respite Care Short-term temporary care — days to weeks — to give family caregivers a break. Full care provided during the stay. Often used after hospitalization or to trial a facility before a permanent placement decision.

Winchester
123
Yes
-
52
Studio / 1 Bed / 2 Bed
The Delaney at The Vale
AL

Assisted Living A licensed, long-term care setting for seniors or individuals with disabilities who need help with daily activities — like bathing, dressing, and medication management — but not 24-hour skilled nursing. Offers housing, meals, and around-the-clock support while aiming to maximize resident independence.

IL

Independent Living Lifestyle-focused communities for older adults offering dining, activities, and transportation with minimal personal care. Best for active, independent seniors who want community without medical support.

MC

Memory Care Secured, specialized care for people living with Alzheimer's or dementia. Staff trained in cognitive impairment, with higher staff-to-resident ratios and an environment designed to reduce confusion and wandering risk.

Woburn
120
No
-
17
Studio / 1 Bed / 2 Bed
Bridges® by EPOCH at Lexington
AL

Assisted Living A licensed, long-term care setting for seniors or individuals with disabilities who need help with daily activities — like bathing, dressing, and medication management — but not 24-hour skilled nursing. Offers housing, meals, and around-the-clock support while aiming to maximize resident independence.

IL

Independent Living Lifestyle-focused communities for older adults offering dining, activities, and transportation with minimal personal care. Best for active, independent seniors who want community without medical support.

MC

Memory Care Secured, specialized care for people living with Alzheimer's or dementia. Staff trained in cognitive impairment, with higher staff-to-resident ratios and an environment designed to reduce confusion and wandering risk.

NH

Nursing Home Licensed facility providing 24/7 skilled nursing care for residents with complex, ongoing medical needs. Staffed by RNs, LPNs, and CNAs. Inspected and star-rated annually by CMS. Accepts Medicare (short-term rehab) and Medicaid (long-term care).

Lexington
48
No
A
12
Studio / 1 Bed / 2 Bed

Living Spaces & Floor Plans

Gables Winchester P2
Gables Winchester P3
Gables Winchester P1

Places of interest near The Gables at Winchester

Address 1.9 miles from city center — 1.93 miles to nearest hospital (Winchester Hospital)

Address 299 Cambridge St, Winchester, MA 01890

Calculate Travel Distance to The Gables at Winchester

Add your location

Address

Guides for Better Senior Living

Care Cost Calculator: See Prices in Your Area

Nursing Home Data Explorer

Don’t Wait Too Long: 7 Red Flag Signs Your Parent Needs Assisted Living Now

The True Cost of Assisted Living in 2025 – And How Families Are Paying For It

Understanding Senior Living Costs: Pricing Models, Discounts & Financial Assistance

Financial Aid for Massachusetts Seniors

Get financial aid guidance

Home Care Program

MassHealth Home Care

Age 60+, Massachusetts resident, at risk of nursing home placement.

~$1,500/month (individual, varies by region).

$2,000 (individual, excludes home, car).

Coordinated through Aging Services Access Points (ASAPs); high demand in urban areas.

Frail Elder Waiver

Massachusetts Medicaid FE Waiver

Age 65+, Massachusetts resident, Medicaid-eligible, nursing home-level care need.

~$2,829/month (300% FBR, individual).

$2,000 (individual), $3,000 (couple).

Requires clinical eligibility determination.

Senior Care Options (SCO)

Massachusetts Senior Care Options

Age 65+, Massachusetts resident, eligible for MassHealth (Medicare optional), nursing home-level care need.

~$2,829/month (300% FBR, individual); QIT allowed.

$2,000 (individual), $3,000 (couple) (excludes home up to $713,000, car).

Not available in Dukes/Nantucket Counties; multiple SCO providers (e.g., CCA, Tufts).

Medicare Savings Program (MSP)

Massachusetts Medicare Savings Program (MassHealth Buy-In)

Age 65+ or disabled, Massachusetts resident, Medicare Part A/B.

~$2,510/month (QMB), ~$3,380/month (SLMB), ~$3,598/month (QI)—individual.

$9,430 (individual), $14,130 (couple).

Three tiers; no waitlist; includes Extra Help for Part D.

National Family Caregiver Support Program (NFCSP) Respite

Massachusetts NFCSP Respite Care

Caregivers of 60+ needing care or 55+ caregivers of others; Massachusetts resident; functional needs (2+ ADLs).

Prioritizes ~$24,980/year (individual); no strict cap.

Not assessed; need-based.

27 ASAPs; prioritizes low-income, rural caregivers.

Prescription Advantage

Massachusetts Prescription Advantage

Age 65+ or disabled, Massachusetts resident, enrolled in Medicare Part D (or ineligible for Medicare).

No strict limit; copays vary by income (~$24,980-$75,000/year individual).

Not assessed.

Supplements Medicare Part D; no enrollment fee for low-income.

Senior Community Service Employment Program (SCSEP)

Massachusetts SCSEP

Age 55+, unemployed, low-income, Massachusetts resident.

~$1,983/month (125% FPL).

Not specified; income-focused.

Priority for veterans, rural residents; AARP partnership.

VA Aid and Attendance (A&A) and Housebound Benefits

Massachusetts VA Aid and Attendance/Housebound

Age 65+ or disabled veteran/spouse, Massachusetts resident, wartime service, need for ADL help (A&A) or homebound.

Net income < ~$1,984/month (veteran with dependent, A&A); pension offsets income.

~$155,356 (net worth limit).

High veteran demand statewide.

More homes from the same owner

Operated by Sinceri Senior Living
Tour Icon
Planning a tour? Check our touring checklist.
Chat Icon
Thinking of living here? We can help you speak to a current resident