Find With Care
1 of 14
community exterior
community exterior

Community profile

Boonesboro Trail Senior Living

2101 Old Boonesboro Rd, Winchester, KY

Assisted LivingMemory CareIndependent Living

★ 4.33 reviewsRead reviews

About the community

About 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.…

Family and resident feedback

4.3 out of 5 from 3 reviews

Recent public reviews can help surface themes to ask about on a tour. Ratings belong to the original review source and are not independently verified by us.

★★★★★

Positive

Our families experience

When it comes to the care services, they are not always quick to respond to the call button when someone calls for assistance. It may be several minutes and multiple rings to get a response from a caregiver. Not sure on the value for cost, I don't have anyplace else to compare it to. I am impressed with the interaction between the many residents, with the staff members, and many visitors that are welcomed there. Many activities going on another same times to meet the mental, physical and emotional needs.

Verified ReviewFamily/friendAssisted Living
See category ratings
Cleanliness
5.0 / 5
Friendliness
5.0 / 5
Care Services
4.0 / 5
Activities
5.0 / 5
Staff
5.0 / 5
Meals & Dining
5.0 / 5
AnonymousJanuary 27, 2026

★★★★★

Positive

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.

Verified ReviewFamily/friendAssisted Living
AnonymousApril 9, 2025

★★★★★

Positive

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.

Family/friendAssisted Living
See category ratings
Cleanliness
5.0 / 5
Friendliness
5.0 / 5
Value for Cost
5.0 / 5
Care Services
5.0 / 5
Activities
5.0 / 5
Staff
5.0 / 5
Meals & Dining
5.0 / 5
Marcia JJune 7, 2024

Verified overview

What we know from public sources

Care options
Assisted Living, Memory Care, Independent Living
Operator
Not yet resolved
Public price status
Not publicly found
Last source check
August 16, 2026

Source-published features

Amenities and services

Grouped so you can scan what affects day-to-day life before opening an operator page.

Meals & dining

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

Health & wellness

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

Services & convenience

  • Housekeeping
  • Beautician
  • Laundry Service / Drycleaning
  • English
  • Resident Parking Available
  • Transportation at Cost
  • Uncovered Parking
  • Cats Allowed
  • Dogs Allowed

Activities & engagement

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

Outdoor spaces

  • Computer or Media Center
  • Indoor Atrium
  • Central Fireplace
  • Fitness Center
  • Piano or Organ
  • Arts and Crafts Center
  • Golf Course or Putting Green
  • Raised Garden Beds
  • Outdoor Common Areas
  • Meeting Room
  • Private Bath
  • Indoor Common Areas
  • Main Street Shops
  • TV Lounge
  • Library
  • Barber Shop
  • Outside Patio
  • Beauty Salon

Apartment & room features

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

Official oversight

Inspection and quality records

Inspection coverage has not yet been completed for this community. “Not covered” is not the same as “no violations found.”

Coverage last checked August 16, 2026.

Questions to confirm with the community

Additional care fees
Not publicly disclosed
Move-in fee
Not publicly disclosed
Exact unit availability
Confirmation required

Compare nearby

Other communities near Winchester

Richmond Place community photo 1

Lexington, KY

Richmond Place

Assisted Living · Memory Care · Independent Living

From $3,300/month

Published price comparison

Nearby starting prices

Highgrove at Tates Creek$2,975/month

Richmond Place$3,300/month

Mayfair Village Retirement Community$3,750/month

Cedarhurst of Beaumont$4,650/month

Cedarhurst of Hamburg$4,900/month

Magnolia Springs Lexington$5,395/month

Operator-published starting prices only; care fees and inclusions differ.

Explore locally

Senior living around Winchester

Assisted living in WinchesterMemory care in WinchesterIndependent living in Winchester

Nearby cities

Continue your search

Mount Sterling, KY14 miles away
Assisted Living · Memory Care · Independent Living
Richmond, KY18 miles away
Assisted Living · Memory Care · Independent Living
Lexington, KY18 miles away
Assisted Living · Memory Care · Independent Living · 55+ communities
Nicholasville, KY23 miles away
Assisted Living · Memory Care · Independent Living · 55+ communities
Carlisle, KY24 miles away
Independent Living
Georgetown, KY26 miles away
Assisted Living · Memory Care · Independent Living
Boonesboro Trail Senior Living – Winchester, KY | Find With Care