Get Free Assistance!
For Pricing, Tours, and Availability at Middleton Crossing:
(800) 755-1458
Trying To Contact a Loved One?
To Reach Residents Living at Middleton Crossing:
(608) 812-8430
About Middleton Crossing – Sky Active Living
Middleton Crossing is the right choice for anyone looking for all that senior living has to offer. Our residents enjoy all the local activities and entertainment that Middleton has to offer. Our community is positioned perfectly for residents to take advantage of local events.
We create a comfortable lifestyle by concentrating on you and your loved ones. We will create a specialized level of care that meets your needs. Our community is filled with people just like you. Our residents rest easy knowing that they live in a safe, worry free environment that allow them lead dignified lives. Friends and relatives are always welcome to come visit you join you for meal in the dining area.
Middleton Crossing Living Options
Independent Living
Healthy seniors in Middleton seeking an active retirement will thrive at Middleton Crossing Independent Living. Enjoy an age-restricted setting, effortless living, and a variety of social activities and events. At Middleton Crossing Independent Living, you can finally make time to pursue your hobbies and interests in retirement.
Schedule Tour at Middleton Crossing – Sky Active Living
By clicking Request Free Info, you agree to our Terms of Use and Privacy Policy. You also consent to receive texts and calls, which may be autodialed, from us and our partner providers; however, your consent is not a condition to using our service.
Middleton Crossing Amenities & Services
We offer seniors the latest amenities in comfort that they would enjoy in the comfort of their own homes. Three Chef Prepared Meals Daily, Full Calendar of Enriching Activities, Complimentary Scheduled Transportation, Weekly Housekeeping, Light Linen Service, Lively Mobile Plus Personal Emergency Response Device, Maintenance, Most Utilities Included are available for all residents. The staff here are fully trained, friendly and accessible. They will help your residents enjoy their stay with us.
Our facility has Activity Room, Barber/Beauty Salon, Business Center, Community Center, Community Fireplace, Community Grounds, Cottages, Fitness Equipment, Game Room, Garden, Large Screen TV Lounge, Laundry Facilities, Library, Locked Mailboxes, Lounge Area, Parking, Patio Area, Pets Welcome, Private Dining Room, Renters Liability Insurance Program, Resident Kitchen, Safety Rails, Smoke Alarm and Sprinkler System, Spa Services, Walking Paths, Wheelchair Accessible, WiFi in Common Areas, and planned activities and events and other ways we keep seniors active and healthy. Our staff works really hard to keep our aging residents active and independent, keeping everyone feeling young and healthy.
Residents enjoy of a full schedule of social, educational and entertaining activities. Our structured program helps all residents maintain a high quality of life. Many of our activities encourage members to socialize and develop friendships with other residents. We make sure the activities are fun and entertaining.
Want to learn more about what our senior living community can offer you? Call (800) 755-1458 for more information.
Middleton Crossing – Sky Active Living Location
Middleton Crossing – Sky Active Living
9401 Old Sauk Rd, Middleton, WI 53562
Pricing & Availability
(800) 755-1458Available Living Options
- Independent Living
Contact Us to Get Pricing & Schedule Tours
* Required FieldsBy clicking Request Free Info, you agree to our Terms of Use and Privacy Policy. You also consent to receive texts and calls, which may be autodialed, from us and our partner providers; however, your consent is not a condition to using our service.
Prefer to speak to a live person? Talk to a local senior living advisor today
(800) 755-1458
Middleton Crossing – Sky Active Living Frequently Asked Questions
What is the pricing for Middleton Crossing – Sky Active Living?
The cost of independent living at Middleton Crossing is determined by the size and floorplan of the unit and the selection of services and amenities. Each resident’s lifestyle needs and preferences are considered in the overall cost. Call (800) 755-1458 for customized quotes and tailored pricing.
Does Middleton Crossing – Sky Active Living accept Medicare or Medicaid?
Medicare does not cover the costs of independent living because these communities are intended for older adults who can live independently without assistance. Independent living does not include medical or custodial care, making it ineligible for Medicare coverage. Medicaid also does not apply, as it is not considered a healthcare service. This is general information, to learn more about your eligibility call (800) 755-1458 to speak to a professional senior advisor.
What types of senior living options are available at Middleton Crossing – Sky Active Living?
Middleton Crossing provides independent living designed to promote independence, wellness, and connection for seniors.
Are there any accommodations currently available at Middleton Crossing – Sky Active Living?
Units at Middleton Crossing fluctuate in availability. Contact (800) 755-1458 to speak with a senior living advisor today.
Does Middleton Crossing – Sky Active Living offer guided tours?
Middleton Crossing welcomes visitors for guided tours. Arrange your visit by calling or filling out the online contact form for scheduling assistance.
How is Middleton Crossing – Sky Active Living ranked compared to other senior living communities?
Middleton Crossing has a 4.5 rating, reflecting excellent reviews. Users were very pleased with the independent living options, highlighting the engaging activities and thoughtful amenities.
Reviews Middleton Crossing – Sky Active Living
April 2026
My sister moved to Middleton Crossings recently. She absolutely loves it!! The three delicious and nutritious meals every day will help keep her healthy. The myriad activities and entertainment will keep her socially engaged. It is the perfect place for her and she has already made friends. The staff and residents are so welcoming and cordial!! I would give ten stars if that were an option!
April 2026
My sister recently moved to Middleton Crossings from South Dakota. She absolutely LOVES it there! She raves about the tasty meals, the activities, and the friendly, welcoming people... staff and residents alike. Her apartment is just perfect for her needs. Knowing she is happy and safe is a huge relief for the family and I would highly recommend Middleton Crossings to anyone!
April 2026
The staff and guests are great! Made me feel right at home
February 2026
Myself and two friends toured Middleton Crossing. Tauny spent a lot of time giving us good information and answering our many questions. Middleton Crossing was very clean and homey. Beautiful artwork in all the halls. They do their best to provide lots of activities and resources to meet the needs of their residents. Thank you!! …
January 2026
Look forward to the move
December 2025
We recently helped a friend find a place. He was in assisted living and had improved to where he could be more independent. He was ready and able to manage his medications, so his medical needs were more minimal, primarily help with eyedrops. We were referred to Middleton Crossing and found that it checked all the boxes for his needs. They had immediate availability and that was a bonus; we were in a tight situation to place him. They also have an affiliated home health care company that bridges the medical care gaps for residents with some needs but largely are capable on their own. They have great staff members and we've found it really is a "community" of staff and residents. It is a very welcoming environment. They are in tune with what's going on with residents. The apartments and common spaces are clean and well kept. Residents are more active and agile than those in assisted living facilities. There are lots of activities and residents participate, adding to the spirit of togetherness and belonging there. We are very thankful and grateful that we found such a great place for our friend and he is on his way to truly thrive there.
December 2025
Taino was a great help! I saw a very nice two bedroom apartment. There is no underground parking & no washer & dryer in the apartment. Other than that, I loved the brightness in the open areas & in the apartment.
December 2025
I took a scheduled tour. Tauni is amazing. She’s caring and very knowledgeable. The building was clean and well cared for. I love all of the windows in each apartment.
August 2025
My mom called Middleton Crossing, a Sky Active Community home for nearly 15 years, and it was such a blessing for her and our family. She always felt happy and engaged there. The activities team offers so many options”from crafts, games, and social events to frequent bus outings for scenic drives, shopping, and lunches at fun restaurants. They also provide transportation a couple of times a week for doctor’s appointments, which was very convenient. Residents receive three meals a day, and the apartments are bright and comfortable. Over the years my mom lived in three different units, and each one had large windows that let in lots of sunlight, along with a patio space she enjoyed spending time on. The staff is warm, supportive, and always willing to help. When my mom passed, they showed incredible compassion, which our family will always remember. I truly appreciate the care and community she experienced during her many years at Middleton Crossing.
July 2025
July 2025
June 2025
Great to visit. Outside planting is great. Don Harris
April 2025
January 2025
I have a friend that moved here recently & yesterday was the 1st time I had been there. Staff was very friendly, apartments are very nice & my friend is very happy there which was a concern of ours.
December 2024
October 2024
I have an elderly family member that recently moved to the Jefferson. It is very clean, has great homemade food, staff is friendly and the residents get to know each other and build friendships. Tauni was very friendly and efficient in assisting with the move and lease documents, understands the needs of the residents and makes them all feel special, and really goes out of her way to make Veterans feel respected. Tauni and her staff go above and beyond normal duties to assist residents when problems arise (medical issues) even when it’s not their job. The service is great, the grounds are clean and beautiful, the communication is very good. Couldn’t ask for more.
April 2024
Holiday Middleton is such a lovely independent living residence for seniors! There's always an activity happening, they treat everyone as an extension of their own family. Huge shout out to Tauni ... she's a bundle of excitement and energy here ... always goes the extra mile for residents and families!! Tauni represents the love and compassion you can expect in the community! Recent apartment renovations -- so beautifully done!
March 2024
My experience with the living conditions at The Jefferson has been very satisfying. When I was searching for the best place I was immediately impressed with the staff. The offices are right inside the front door and the office doors are open and available to whomever has a need to be met. Staff are working in the dining room at mealtimes and very involved with the residents of The Jefferson. Have a question? Someone will respond or find a solution. It’s a friendly and accommodating facility. Staff support the residents in making their lives valuable and enjoyable Anne Hecht
March 2024
I moved my mom into the Holiday Middleton and have been very pleased with the living arrangements and the friendly staff and activities. Grateful for this excellent facility!
March 2024
Holiday-Middleton is better than other assisted living communities I've seen. The main evidence to me as my friend's caretaker is the relatively slow staff turnover. Having experienced caregivers is HUGE! Workers seem well cross-trained, happy to serve there and almost to a person are models of respect, patience and kindness. Even though they don't provide nursing home services, they can recommend and vouch for supplemental, convenient, local personal care to purchase. Within practical limits they often find creative ways to meet individual needs of a very diverse community. Veteran-friendly. GLBTQ-friendly. Pet-friendly! Two evenings a week residents can listen in on a community band practice. They are right-sized so that residents and staff can get to know one another and participate together.
February 2024
The staff is thoroughly competent, hardworking, and kind. I am very happy to settle here, and delighted with the consistently good food. I have no idea how the Holiday Middletown managed to make this such a pleasant place.
October 2023
The Jefferson is simply amazing! There's always an activity happening, they've got great food, and treat everyone as an extension of their own family. The administration is always welcoming and happy to see you!
September 2023
I work for a small, non-profit Guardianship located in Madison WI. Thanks to one of our clients, we found The Jefferson! I can say that over the past five years, I have frequented The Jefferson week after week to consistently discover a happy and healthy community guided by staff who truly care. I currently visit two residents of the community who absolutely love it there. I'm fortunate to have been invited to stick around for meals which are served in a spacious dining room, so delicious and all meals are included in resident rents! Each meal of the day offers residents multiple options. The Jefferson has a lot of amenities and additional ala-carte services should you or your loved one need them. The grounds are well maintained and making four laps around the building allows active folks a nice mile long walk in a safe neighborhood bustling with beautiful landscaping, wild birds and squirrels. I can't say enough about the warmth and receptivity of the staff and the community itself. Each time I arrive, I'm greeted by friendly faces from the staff and residents alike. I've actually made quite a few friends there. There's an onsite Salon with two stylists who do great work for the residents of The Jefferson, both of my clients rave about their stylists. There are multiple common areas for residents to enjoy activities and various clubs run by fellow residents. When I'm ready to seek out a Senior Living Community in my golden years, I'm quite sure I've already found it! It's worth a visit and I'm sure you'll settle in well should you choose to make it your home!
September 2023
"We adjusted in about five minutes."
June 2023
After touring several Independent Senior Living facilities my 99 year old mother picked The Jefferson. She is very happy with her decision. The staff are very caring and friendly. She loves that all her meals are provided and she does not have to cook anymore. When I visit she always tells me "I haven't had a bad meal yet". She loves having her hair and nails done right in the facility. She likes the fact that she can get other services such as physical therapy there also. They have been very responsive to her needs and requests. After living in her home for 52 years, she has settled in very quickly and has met many wonderful residents.
May 2023
May 2023
This community has great food and wonderful activities
May 2023
March 2023
A wonderful retirement community, caring and respectful staff, - making this community a home.
March 2023
October 2022
July 2022
In 11 ears,four quarantines abd Covid, they never missed serving a meal! STAFF ARE FRIENDLY,FUN AND CARING.This is my last week.They will all be MISSED!
July 2022
Nice place with nice communitybut, be aware that if you sign a lease, make sure that it is signed in the month that you start to live there. I signed the lease for my 88 year old mother the day before September 1 and the anniversary ( when the rent can be increased) became the month before, in August, just because I signed one day prior to September. This does not seem fair at all, but is supposedly in the lease. Also be aware of the high pressure that the salesperson may put on you. My mom could not move in until October, but I was told that if I didn’t rent it in September, there might not be an apartment available in October. She paid rent for an extra month and had no meals or anything at that time. Also be aware of the activity fee. One year later I was told that there was a special when I signed the lease with reduced activity fee but I was not made aware of this. I thought the $1,000 one time fee was excessive at the time as it was! Ask a lot of questions and get everything in writing! The facility is quiet and there are lots of activities for the elderly. I recommend it if you are aware of all the fees!
July 2022
February 2022
Senior living and residents seemed happy. Clean
January 2022
I just moved my brother into The Jefferson. The entire experience has been nothing less than stellar. From the moment I asked for resources at the VA and was told there were 3 places that would be a good fit, I got a call from Tauni at The Jefferson in about 20 minutes! She asked lots of questions about his needs and we went for a tour and lunch the very next day. The staff was very welcoming, the residents all seemed genuinely happy and social, the place was clean and the food was amazing! I thought moving my brother was going to be difficult, but after he visited he was even impressed and the decision to move was easy for him. The lease was signed that day and he was moved in within 3 days. I had so many questions about the onsite services provided (shuttle bus for his doctor visits, the on site nursing visits for medications, barber, foot care etc) everyone was super patient and helpful, they all listened and were all very quick to respond and my requests were never forgotten. We had some maintenance requests that were handled right away, I never had to ask twice! When I followed up with my brothers doctor to let her know that he moved into The Jefferson she was very pleased. She said she has had other patients who moved here and they thrived. I can see why! Also, lots of folks have their pets there, its very dog friendly, its just so wonderful. For as busy as it is, there are also lots of special quieter places like a library, an activity room, a TV room and even a chapel. Of course we are in the honeymoon phase, but I have high hopes for my brothers future here. Check them out! One of the other three places called me back a week later. Epic fail!
December 2021
I’ve visited some clients here. The rooms are very size-able and I have not had any issues with customer service.
December 2021
My 95-year-old mom lived at the Jefferson for a year. It was a wonderful place for her. She loved the food. She loved the staff. She loved socializing with other residents. I visited her nearly every day and would speak with the staff and other residents. I found the staff incredibly compassionate and professional. The building was also impeccably maintained. When I brought problems to the attention of staff they were remedied very quickly. I believe the staff truly cares about residents and works hard to make the Jefferson a warm, safe, hospitable”and fun place for residents. I would have loved for my mom to continue living there in her bright, airy apartment and with the Jefferson’s conscientious staff, but sadly her dementia progressed to the point that she needed 24-hour care. The Jefferson is not assisted living, although RecoverCare aids can be hired for things like medication help, bathing, etc. And there are other visiting nursing services that visit the Jefferson. It was a good place for my mom to live during a tough period in her life. I recommend the Jefferson, highly, but one must honestly assess the level of care a loved one needs.
November 2021
September 2021
July 2021
Mom has been happy there.
November 2020
We just had our first tour. The folks that work there are TOP notch! Very friendly and helpful. Very impressed with the amenities offered, something for every one. They seem to sincerely care about their residents. The only reason I did not give them a higher rating is that is that is is getting just a bit older. Not a deal breaker though. The price is very fair for what you get in my opinion.
September 2020
Caring place.
July 2020
February 2020
October 2019
October 2019
Quiet
August 2019
Lovely place, lots of socializing, MIL is happier.
July 2019
Great restaurant chef prepared meals! Staff is fun!
May 2019
Love this place.
March 2019
October 2018
Wow! This is where I wanna be when I get to my retirement age and above!
September 2018
August 2018
My parents have been Living at The Jefferson for several years. They are moving out soon only because they need assisted living, otherwise I'd be happy for them to stay right where they are. The staff at The Jefferson clearly care about the residents. During my visit each Monday evening I watch the interactions, and there's a clear fondness there. There are always a lot of activities going on, even if my parents didn't take advantage of them very much :o) I enjoy the food there, especially the soups, which are absolutely outstanding! It's been very convenient for my parents to be able to get PT with Recover Care, who are also housed in the building. If the five stars don't indicate it, I give The Jefferson an unreserved recommendation.
July 2018
Moved my ex-father-in-law in there. Seems like a nice place.
July 2018
March 2018
December 2017
Nice Place
November 2017
Management and staff are great.
November 2017
Visit here for work only.
November 2017
Seems like a very nice retirement home. A good number of activities.
September 2017
September 2017
Great place
August 2017
Rate and Review Middleton Crossing – Sky Active Living
Communities Near Middleton
View all communities near Middleton
Assisted Living Center is not affiliated with Middleton Crossing – Sky Active Living and does not guarantee the completeness or accuracy of pricing, photos, living or care available, services or amenities. All phone calls and form submissions are handled by our trusted partner A Place for Mom. Any information regarding Medicare and Medicaid is for general informational purposes and is not a substitute for professional advice. Please visit Medicare.gov or Medicaid.gov for more information.
Families and their loved ones are encouraged to do the following before deciding on a community.
- Schedule a tour and visit the physical location to make sure community description is accurate.
- Confirm with community manager that living and services required for you or your loved one's unique needs and budget are met.
- Check with state government websites for additional provider licensing and information.
If there is any information that is inaccurate or needs to be updated, please contact Assisted Living Center.
Assisted Living Center uses the term "assisted living" or "personal care" to inform users that a community provides assistance with some Activities of Daily Living (ADL's). It may not meet your state's legal definition required for that level of care.