Leland Home

Step inside Wingate Living and you’ll see that we build more than beautiful residences for older adults. We’re builders of friendships and Senior Living Communities that make you feel right at home.

Welcome to Winning Farm - A Distinctive 55+ Community, your premier choice for long-term care in the heart of Winchester, MA. We are dedicated to providing a warm and inviting environment for our residents, where they can truly feel at home. At Winning Farm, we understand that the transition to a retirement community can be both exciting and overwhelming. That's why our team of dedicated professionals is here to support you every step of the way. Our focus is on providing comprehensive care that meets the unique needs of each resident, promoting independence and enhancing quality of life. Our community boasts a range of top-notch services and amenities to ensure that our residents enjoy a fulfilling and comfortable lifestyle. From spacious and well-appointed living spaces to beautifully landscaped grounds, every detail has been carefully considered to create a welcoming and serene environment. As part of our commitment to fostering a vibrant and engaging community, we offer an array of activities and social events. Whether it's participating in fitness classes, joining a book club, or exploring local attractions, our residents have plenty of opportunities to connect with others and pursue their passions. For those who require professional care services, our highly trained staff is available around the clock to provide compassionate and personalized assistance. Our team is committed to working closely with residents and their families to develop customized care plans that address individual needs and preferences. At Winning Farm, we believe that exceptional care should also come with exceptional perks. Our community features delicious dining options prepared by our talented culinary team, ensuring every meal is a delightful experience. Additionally, our convenient amenities, such as transportation services and housekeeping, further enhance the comfort and convenience of our residents' daily lives. We invite you to experience the Winning Farm difference. Discover a community where compassionate care, a welcoming atmosphere, and a host of amenities converge to create a truly distinctive 55+ living experience. Contact us today to schedule a tour and see firsthand how Winning Farm can be the perfect place to call home.

The Little Sisters of the Poor are an international congregation of Roman Catholic women religious. Our MISSION is to offer the neediest elderly of every race and religion care and a home where they will be welcomed as Christ.