We wanted to be fairly close to major shopping for groceries such as big box stores so we bought a resale about 8 miles away.

No desire to be say 18 miles away down south.

However what is important to us may not be to you

No, it's always been bad and by the time construction is completed so will all those new family homes be completed adding thousands more vehicles to that area. People that liver there are already complaining and they haven't even completed one home yet.
I quit driving up there over a year ago and won't go back, nothing up there that I need that I can't get down here or in southern Leesburg.

South of 44 you're closer to Orlando. :) Depends on what kind of "shopping" you need or want. If it's just FOOD then you have no problem. If it's hardware stores, big box stores, a lot more restaurants, a lot more gas stations (so lower prices in many cases). Depends on what your lifestyle demands. Being from NNJ/NYC area we like a LOT of shopping areas not filled just with Cremation companies, nail salons, banks and financial services ;) but we have adjusted a bit but find ourselves going to Orlando more often than planned. :D

We are just north of 466A equidistant (~6miles) between Brownwood & 441 and pretty close (3 miles) to LSL and chose that location for a weird but specific reason. :)

We are 11 minutes to BW, 14 minutes to LSL, by cart. Have access to 3 grocery (Publix, Winn Dixie, Walmart) in 10 minutes or less, by car/cart.

Yet I travel to Fresh Market, Earth Fare, Whole Foods, Costco, Commissary. I buy gas at Sam’s, while shopping, maybe once a month. So no living near shopping that is available in TV is not important to me. But you will be entirely different in your quest compared to my needs

We like being near a Publix/Winn Dixie. We are close to both
We would place being close to restaurants pretty high too. But we eat out fairly often.

With Amaxon, who cares?

Kroger delivers groceries.

Plenty of up to date shopping south of the Turnpike within 20 min in Leesburg and Clairmount.l (Costco, BJ's, Walmart, Target, etc.) Tampa is 45 min, Orlando/Disney Springs less than 60.

As others have stated, traffic is a mess in SS. Businesses are old and the homeless are stalking some big chain parking lots...

where is the closest hospital? ER? Urgent care? Doctors, Dentists offices? these are questions you should be asking yourself....not restaurants.

Not much convenient south of 44. Plan to travel for most things including golf if you play.

I wasn’t sure at first, we have been here almost a year now and can whole heartily say we love being a bit away from a major shopping plaza for the reasons you have mentioned, congestion and traffic. We bought a home south in Citrus Grove.
Love life in The Villages.

Absolutely fine. I would rather not have all the traffic that so many stores brings.

Route 44 has two Publix grocery stores already for several years. And Route 301 has two gas stations what's always seem to overcharge more and those on 44. But I bet in two or three years you'll have half a dozen decent largest stores for shopping but of course there's always Amazon and walmart.com so really what do you need? For Hardware go up 301 a few miles is in Ace Hardware and on 44 is sparr. If I were you I would be more concerned with the lack of doctor's offices and Specialists currently in the in the area although there are several Urgent Care facilities already on 44 10 minutes from anywhere near you. Remember the hospitals that are nearest to you or at least going to be 20 minutes or more. I'm talking about Advent Leesburg and The Villages Hospital

You already have it figured out; I agree with you about shopping and you will be happy down south. Don't listen to those who bash the newest areas-I am very happy shopping at our grocery store at Magnolia Plaza and otherwise shop online or in Orlando for better options than along 441/27. Welcome.

"If you build it, they will come..."

I remember our first trip to TV, some years back. Some of the prime retail outlets today rest on what was pasture or scrubland then. It won't be long until those types of businesses are built in the south too.

I wouldn’t live North of LSL. Too much traffic compared to the south end of TV. Personally, I like not having big box stores around. Less traffic and if I must go to a big box store it’s a close drive.

Convenience is exactly why 17 years ago we bought close to 466. We really want for nothing as we have a ton of choices. Publix, Walmart, Aldi, Fresh Market, Sprouts coming, Homegoods, Wallgreens and CVS. By golf cart we can get to all of these in time from 2 minutes to 10 minutes. This convenience is why homes in this area sell super-fast.