About Assisted LivingAssisted living facilities offer housing and care for active seniors who may need support with activities of daily living, like bathing, dressing, and medication management.Complete guide to assisted livingBest of 2025 Assisted Living Winners
About Memory CareMemory care facilities provide housing, care, and therapies for seniors who have Alzheimer’s disease or other forms of dementia in an environment designed to reduce confusion and prevent wandering. Complete guide to memory careBest of 2025 Memory Care Winners
About Independent LivingIndependent living facilities offer convenient, hassle-free living in a social environment for seniors who are active, healthy, and able to live on their own.Complete guide to independent livingBest of 2025 Independent Living Winners
About Senior LivingSenior living is a term used to describe various housing and care options for older adults from maintenance-free, 55+ facilities for active seniors, to secure, fully staffed facilities for seniors with Alzheimer's or dementia. Complete guide to senior livingFind senior living facilities near you
About Nursing HomesNursing homes provide short-and long-term care for seniors who have physical or mental health conditions that require 24-hour nursing and personal care.Complete guide to Nursing Homes
About Senior ApartmentsSenior apartments offer accessible, no-frills living for seniors who are generally active, healthy, and able to live on their own.Complete guide to Senior Apartments
About Care HomesResidential care homes are shared neighborhood homes for seniors who need a live-in caregiver to assist with activities of daily living, like dressing and bathing.Complete guide to care homes
Veteran ResourcesVA benefits for long-term care, such as Aid and Attendance benefits, can help eligible veterans and their surviving spouses pay for senior care.Guide to VA benefits for long-term care
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Boonesboro Trail Senior Living

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2101 Old Boonesboro Rd, Winchester, KY 40391

For pricing & availability:
(866) 374-4058
8.5
Review score
2 reviews
Add review
8.5
Review score
2 reviews
5 star
100%
4 star
0%
3 star
0%
2 star
0%
1 star
0%
See all reviews
7.4
Review score
388 reviews
102 facilities
Boonesboro Trail Senior Living
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Boonesboro Trail Senior Living community exterior
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Anonymous
-
Sibling of resident/client
5.0
Boonesboro Trail
I know several people who do live there and they all seem to love the food and camaraderie with Winchester friends. I have only heard from one client there that if you push the button on the necklace you wear around your neck, it might take awhile to get someone to come and help you. We wo

About the facility
Boonesboro Trail Senior Living

Boonesboro Trail Senior Living is a senior living community in Winchester, Kentucky, that offers quality care in a vibrant environment. Professional staff assist with a variety of health and personal care needs ranging from memory care to activities of daily living such as bathing, grooming, dressing, medication management, and more.

Enjoy peace of mind and a stress-free lifestyle at Boonesboro Trail Senior Living. They have a 24/7 emergency call system, as well as on-site nursing and wellness team members to offer residents assistance at all times. Staff also takes care of the housekeeping and chores so you can focus on pursuing new hobbies, spending time with friends, relaxing, or participating in fulfilling activities.

Residents have access to a variety of unique community perks and wellness programs, too. Use the art room, game room, theater, and more. Choose from a studio, a one- or two-bedroom apartment, or a semi-private room.

State Licensing Information

To explore the licensing information and compliance histories of senior living communities in the state of Kentucky, visit the Kentucky Department for Aging and Independent Living directory.

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Read more

Senior living options offered

Assisted Living

Memory Care

Pricing
for Boonesboro Trail Senior Living

Total monthly costs depend on room type, select services, and the level of care needed.

Base fees by care type

Assisted Living

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Studio
Starting at $XXXX/mo
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1 Bedroom
Starting at $XXXX/mo
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2 Bedrooms
Starting at $XXXX/mo

Memory Care

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Studio
Starting at $XXXX/mo
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2 Bedrooms
Starting at $XXXX/mo
*Prices quoted are monthly rental charges and are provided by the communities themselves. Actual prices may differ due to one-time fees, timing and care services required. Speak with your Senior Living Advisor to learn more.

Tours
at Boonesboro Trail Senior Living

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Boonesboro Trail Senior Living community exterior
Boonesboro Trail Senior Living

2101 Old Boonesboro Rd, Winchester, KY 40391

Richmond Place
Richmond Place

3051 Rio Dosa Drive, Lexington, KY 40509

Seacoast at Liberty Ridge
Seacoast at Liberty Ridge

701 Liberty Ridge Lane, Lexington, KY 40509

Preston Greens Senior Living
Preston Greens Senior Living

1825 Little Herb Way, Lexington, KY 40509

8.5
Review score
2 reviews
8.5
Review score
2 reviews
5 star
100%
4 star
0%
3 star
0%
2 star
0%
1 star
0%
9.6
Review score
155 reviews
9.6
Review score
155 reviews
5 star
56%
4 star
27%
3 star
8%
2 star
6%
1 star
3%
9.0
Review score
31 reviews
9.0
Review score
31 reviews
5 star
59%
4 star
29%
3 star
6%
2 star
3%
1 star
3%
8.8
Review score
35 reviews
8.8
Review score
35 reviews
5 star
46%
4 star
34%
3 star
11%
2 star
3%
1 star
6%
Studio
Starting at $X,XXX/mo
Studio
Starting at $X,XXX/mo
Studio
Starting at $X,XXX/mo
Studio
Starting at $X,XXX/mo
1 bedroom
Starting at $X,XXX/mo
1 bedroom
Starting at $X,XXX/mo
1 bedroom
Starting at $X,XXX/mo
1 bedroom
Starting at $X,XXX/mo
2 bedrooms
Starting at $X,XXX/mo
2 bedrooms
Starting at $X,XXX/mo
2 bedrooms
Starting at $X,XXX/mo
2 bedrooms
Starting at $X,XXX/mo

Active promotion

No

Active promotion

No

Active promotion

No

Active promotion

No

Pet friendly

Yes

Pet friendly

Yes

Pet friendly

Yes

Pet friendly

Yes

Care types offered

2

Assisted Living, Memory Care

Care types offered

3

Assisted Living, Memory Care, Independent Living

Care types offered

2

Assisted Living, Memory Care

Care types offered

2

Assisted Living, Memory Care

Amenities
at Boonesboro Trail Senior Living

Healthcare Services

  • Staffing & Ancillary Services
  • Incontinence Care
  • Diabetic Care
  • Memory Care
  • High Acuity Care
  • Non-Ambulatory Care
  • Medication Management

Meals & Dining

  • No Sugar
  • Gluten-free
  • Professional Chef
  • Guest Meals
  • Restaurant Style Dining
  • Vegan
  • Pureed Meals
  • Organic
  • International Cuisine
  • Vegetarian
  • Special Dining Programs
  • Low / No Sodium
  • Room Service
  • Kosher
  • Meals Provided

Room Amenities

  • Respite or Short Term Stays Offered
  • Garden View
  • Kitchenette
  • Wi-Fi/high-speed internet
  • Ground Floor Units
  • Air Conditioned
  • Handicap Accessible
  • Wheelchair Accessible Showers
  • Cable or Satellite TV

Community Amenities

On-site dining options

  • Café or Bistro
  • Bar or Pub
  • Private Dining Room

Transportation & parking

  • Resident Parking Available
  • Uncovered Parking
  • Transportation at Cost

Pets

  • Dogs Allowed
  • Cats Allowed

Common areas

  • Private Bath
  • Indoor Common Areas
  • Library
  • Outdoor Common Areas
  • Barber Shop
  • Computer or Media Center
  • Meeting Room
  • Beauty Salon
  • Outside Patio
  • Main Street Shops
  • Central Fireplace
  • TV Lounge
  • Indoor Atrium

Recreational areas

  • Golf Course or Putting Green
  • Arts and Crafts Center
  • Fitness Center
  • Piano or Organ
  • Raised Garden Beds

Services

  • Housekeeping
  • Laundry Service / Drycleaning
  • Beautician

Languages spoken

  • English

Activities

  • Yoga / Chair Yoga
  • Bible Study Group
  • Catholic Services
  • Mormon/LDS Services
  • Visiting Chaplain or Priest
  • Jewish Services
  • Men's Club
  • Holiday Parties
  • Day Trips and Outings
  • Islamic Services
  • Book Club
  • Cooking Classes
  • Other Religious Services
  • Happy Hour
  • Light Therapy Programs
  • Sensory-based Programs
  • Activities On-site
  • Walking Club
  • Live Dance or Theater Performances
  • BBQs or Picnics
  • Protestant Services
  • Adventist Services
  • Christian Services
  • Wii Bowling
  • Intergenerational Programs
  • Cards / Pinochle Club
  • Bridge Club
  • Quilting or Sewing Club
  • Stretching Classes
  • Gardening Club
  • Live Well Programs
  • Trivia Games
  • Karaoke
  • Community Service Organizations
  • Dances
  • Buddhist Services
  • Reminiscence Programs
  • Cooking Club
  • Birthday Parties
  • Educational Speakers / Life Long Learning
  • Devotional Activities On-Site
  • Art Classes
  • Brain fitness / Dakim
  • Resident Band or Musicians
  • Current Events Club
  • Wine Tasting
  • Devotional Activities Offsite
  • Activities Off-site
  • Live Musical Performances

Reviews

for Boonesboro Trail Senior Living

8.5Review score2 reviews
8.5
Review score
2 reviews
5 star
100%
4 star
0%
3 star
0%
2 star
0%
1 star
0%
Trilogy Health Services
7.4
Review score388 reviews102 communities
Write a review
A Place for Mom has scored Boonesboro Trail Senior Living with 8.5 out of 10 using our proprietary review score based on 2 reviews in the last 2 years. Over all time, Boonesboro Trail Senior Living has 2 reviews with an average "overall experience" of 5 out of 5.
Overall Experience
5.0
Cleanliness
5.0
Friendliness
5.0
Care Services
5.0
Staff
5.0
Meals & Dining
5.0
Activities
5.0
Value for Cost
5.0
A Place for Mom has scored Boonesboro Trail Senior Living with 8.5 out of 10 using our proprietary review score based on 2 reviews in the last 2 years. Over all time, Boonesboro Trail Senior Living has 2 reviews with an average "overall experience" of 5 out of 5.
Parent company
Trilogy Health Services
7.4
Review score388 reviews102 communities
Filters
Overall Experience
Date Submitted
Reviewer
Care Received
Verified Review
A Place For Mom has verified the person writing the review and their connection to the community.
1-2 of 2 reviews
Anonymous - Family/friend
Assisted Living
April 9, 2025
5.0
Verified Review
Boonesboro Trail
I know several people who do live there and they all seem to love the food and camaraderie with Winchester friends. I have only heard from one client there that if you push the button on the necklace you wear around your neck, it might take awhile to get someone to come and help you. We wondered together if there could be an emergency code like 3 pushes in a row for "need help immediately " like an SOS!! It is a nice facility and my brother enjoyed living there.
Response from Boonesboro Trail Senior Living
October 4, 2025
Thank you for sharing your thoughts! We’re glad to hear your brother enjoyed his time and that the food and camaraderie stood out. We also appreciate the suggestion about improving response times—it’s great feedback as we continue striving for excellence and resident safety.
Marcia J - Family/friend
Assisted Living
June 7, 2024
5.0
Great Place for Mom!!
Expensive to sign in but then the third month was free so that was really nice! Everything is clean and nice. People are friendly and lots of familiar faces from the community of Winchester. Plenty of meal services, a small gym, and activities for all.
Cleanliness
5
Friendliness
5
Value for Cost
5
Care Services
5
Activities
5
Staff
5
Meals & Dining
5
Viewing 1-2 out of 2 reviews

Neighborhoods
around Boonesboro Trail Senior Living

See what the neighborhood has to offer and what’s nearby:
Boonesboro Trail Senior Living in google map

Tips for evaluating your community options

Safety is a primary concern when seniors and their families look for Assisted Living. To ensure that a community meets your needs and expectations, we recommend that seniors and family members:

  • Know Kentucky’s regulations for memory care. Each state has its own laws and inspection processes to ensure seniors reside in a safe environment. Depending on your state, you may even be able to look up inspection reports for the communities you’re considering. Learn more about Kentucky’s regulations for memory care and download the Guide to Senior Living Licensure and Inspection Reports.

  • Tour the location. Touring allows you to speak to current residents and staff, and it helps you confirm the accuracy of the community description and photos. Use our touring checklist to help guide your visit.

  • Confirm the availability of required services. Before committing, make sure that the community offers all the services your loved one needs, and that those services can be provided within your budget.

Frequently Asked Questions
about Boonesboro Trail Senior Living

Boonesboro Trail Senior Living offers Studio, 1 Bedroom and 2 Bedrooms. Learn more.
A Place for Mom has scored Boonesboro Trail Senior Living 8.5 out of 10 using our proprietary review score.   We assign review scores to give a more reliable view into senior living communities and home care agencies. Our review scores prioritize reviews that are recent — the past 24 months — because we know families need current information when choosing senior care.   Those with many recent, positive reviews receive a high review score, while providers with few recent reviews — regardless of how positive — receive a lower review score. Communities with no recent reviews will not have a review score, even if older reviews are positive. The maximum A Place for Mom review score a community can receive is 10 points.
Call (859) 236-9644 to reach a resident at Boonesboro Trail Senior Living.
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