Middleton Crossing – Senior Living in Middleton, WI
Independent Living

Middleton Crossing – Senior Living in Middleton, WI

At Middleton Crossing, your next adventure starts here. Our independent living community is designed for active older adults who want to enjoy freedom, friendships, and the convenience of maintenance-free living. With beautifully designed apartments, abundant amenities, and a vibrant social calendar, you’ll have everything you need to thrive.

Middleton Crossing front entrance
Middleton Crossing courtyard
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About Middleton Crossing

Discover the perfect balance of comfort and connection. At Middleton Crossing, we provide a welcoming home where you can live independently while enjoying engaging programs, chef-prepared meals, and access to resort-style amenities. Whether it’s relaxing in the library, joining a fitness class, or strolling the landscaped grounds with your pet, you’ll always find something to brighten your day.

Senior Living Pricing

Pricing depends on care needs and apartment choice, but transparent starting rates make planning easier.

  • Independent Living starts at $3,015 per month

Included in monthly rent:

  • Three daily meals + snacks
  • Activities and social programs
  • Housekeeping and laundry
  • Maintenance and security

Services & Care Options

Resident enjoying independent living

Independent Living

Live on your terms in a maintenance-free apartment with dining, housekeeping, and engaging programs.

Learn More

Explore Our Floor Plans

Our community offers a range of studio, one-bedroom, and two-bedroom apartments designed with seniors in mind. Each layout includes modern finishes, spacious closets, and built-in safety features so you can feel right at home.


Independent Living Floorplans

Studio

396 – 578 sq. ft

One Bedroom

396 – 578 sq. ft

Two Bedroom

937 – 975 sq. ft

What Our Residents & Families Say

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Mary Abbott
16 April 2026
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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!
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PICA GUAM
3 April 2026
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The staff and guests are great! Made me feel right at home
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Catherine Kennedy
26 February 2026
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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!! 🌅
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Patrick Cantwell
23 January 2026
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Look forward to the move
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Trish wineke
19 December 2025
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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.
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Sandy Terrill
19 December 2025
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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.
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Sheri W.
27 August 2025
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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.
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Don Harris
16 June 2025
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Great to visit. Outside planting is great. Don Harris
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mary roelke
25 January 2025
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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.
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Claire M
13 April 2024
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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!

Community Life at Middleton Crossing

Here, you’ll find plenty of ways to stay active, social, and inspired. Residents enjoy:

  • Clubs for cards, books, gardening, and current events
  • Daily fitness classes, tai chi, and walking groups
  • Live entertainment, themed parties, and educational speakers
  • Religious services, devotional activities, and intergenerational programs
  • Outings to nearby shops, restaurants, and parks

On-site amenities include:

  • Fitness center and activity room
  • Library and large-screen TV lounge
  • Full-service spa and beauty salon
  • Landscaped courtyards with walking paths
  • Restaurant-style dining room
  • Transportation services

Awards & Recognition for Middleton Crossing – Sky Active Living

  • Caring Star
    Caring Star – 2026
    Awarded by Caring.com
  • Best of Senior Living
    Best of Senior Living – 2025
    Awarded by A Place For Mom
  • Best Senior Living
    Best Senior Living – 2025
    Awarded by U.S. News

In the Middleton Area

Located in a prime spot between city convenience and natural beauty, Middleton Crossing offers easy access to local attractions, shopping, and recreation.

Nearby:

  • Parks: Voss Park, Sauk Heights Park
  • Shopping: Middleton Station, Greenway Station, Target, Costco
  • Dining: Hubbard Avenue Diner, Craftsman Table & Tap, Biaggi’s Ristorante Italiano
  • Medical: UW Health Middleton, SSM Health St. Mary’s Hospital
Senior with his pet dog at a senior community

Pet Friendly

We know pets bring joy and companionship, which is why we welcome them as part of our community. At Middleton Crossing, residents enjoy pet-friendly apartments and walking areas.