Of course everyone’s needs are different so nobody can really answer for the OP.
But I think it’s a lot more than just grocery shopping to consider when choosing a place to live.
In a typical week or month between the two of us we make:

- 2 to 3 trips monthly to Walgreens for medications
- Maybe 2 Dr appointments monthly on 441
- 2 to 3 visits to the gym weekly
- Trip to gas station every couple weeks for car and every month for each golf cart
- softball games near 466 two times a week
- monthly club meetings at Lake Miona and La Hacienda
- golf 2 to 3 times a week
- trip to Sam’s every 3 or 4 weeks
- trip to Lowes every month or so (or 3 times in a weekend if doing a project!)
- dentist is on 466
- Savanah Center or The Sharron for show every month or so
- Out for dinner once a week
- Walmart once a month

All these things can be done from south of 44, but for us it would much less convenient. To each their own.

Most of those things can be done south of 466a, a few of those things can be done at sumter like going to new movies or the square.
Check out the golf cart paths south of 44, check out the bike/walking paths we have south of 44, no other place in the villages have these types of paths. Most golf cart paths south of 466a are off the main road whereas north of 466: aren’t. Brand new health care centers are aplenty around 44. The only establishment that is on the north side in Spanish springs are 2 bowling alleys, so we go to leesburg which is closer and faster to get too.
The op needs to spend a week with a golf cart/bikes/car and check everything out.

South of 44
 

I would be more worried about Freeway noise, prison noise or quarry blasting noise than shopping issues!?

In person shopping may not matter to you but it does to me. Sometimes I need to shop in person; on line shopping often doesnt work.

I have to try on shoes before buying bcs I have foot issues. I like to try on clothing bcs clothes look different on me than on the model & I seem to be btwn sizes.

The Millennial Mall is near Orlando but my house is near LSL so its a long drive.

The Tampa Bay Internationa Mall is nice then the Mall at Millenia.

It's important to me to be near shopping, because I enjoy the adventure. I don't buy much, ever. I'm not a big-time consumer, I make whatever gifts I give to people rather than buy them (most of the time). But I love window shopping, people watching, the experience of shopping in and of itself.

I love parking my golf cart at Petco and walking all the way down to Ulta, stopping in the different stores that have interesting things for sale just to see them. I don't need to fill my house with doodads, when I can see them on display for free.

Coffeebean, this is so true. I have always lived in the NYC metro area. I take the subway or walk bcs both are faster & more pleasant than driving

Thanks!
I didnt know about the Tampa mall. I have a friend who lives near Tarpin Lake so I will take a look next time I go to see her.

We spent a month before buying and could have easily doubled it

I agree - that’s why we live just south of 466A

Shopping was 5 min away north or south where I had lived before TV. The bottle water refill station was a traffic light away. That was a huge convenience. I don't feel like driving 16 min to walmart in comparison, or 24 min to Lady Lake. Before I could just go for a quick run, now I have to time it so I'm not wasting gas going as often or my food isn't running out. Love living here so won't complain too harshly, have to adjust the best way possible. But I just get lazy and have to manage my food stash better to where if I want something I have it and don't have to make a special trip more than 1 a week.

We chose…
 

For us what made the difference was the design of the kitchen counters where the sink and dishwasher are, the home sizes, the new design of the floor plans, the number of bedrooms, being able to have a new home with new appliances, a new roof, new HVAC system, and the chance to expand the rooms, lanai, and garage. A new house also comes with more energy efficiency as the technology gets better. This includes more efficient appliances, windows, and HVAC including the air conditioner. We are south of 44 and love it here!

I live near 441 and SO happy to be near everything. Especially when I was updating my home. Couldn't imagine having to drive 40 minutes to get to a Home Depot. Especially with the cost of gas now, you may regret being isolated from shops and restaurants.

shopping...
 

I don't live south of 44 but right near Sumter Landing. Shopping isn't important to me at all anymore and with you Michael on line does it.

Sometimes we'll take the trek to Ocala for Hobby Lobby or whatever is there but as long as I can get to the WD I'm happy! I'm with you...close to grocery but a bit away from plazas!

I'm in the middle to Publix and Walmart Grocery on 466A one way and Winn Dixie the other way at LSL. Hubby teases me that if I miss a couple of days going to Publix, they are going to get a search party out for. LOL. I feel your pain.