Does not really matter who owns that land at that point, people needed places to shop and had to drive a long way for a long time. As the villages move south same thing will happen.

Thank you for posting the link of activities in The Villages. On that site and from your phone, would you know how to find out the details of the event?

NY Bob...go to districtgov.org for all events happening in the villages

No, at the point that development at Trailwinds started, people were already shopping at Winn-Dixie and eating at Square1, Darrel’s, and Roberto’s. They were buying gas at Marathon and picking up prescriptions at Walgreens. That development added variety (as well as more apartments) but people didn’t have to drive a long way for a long time.

EDIT: It has been mentioned several times that the Villages applied to develop that area but were rejected by the city of Wildwood. The Trailwinds commercial (and residential) development is still being built out today partly because the Villages Developer was denied the opportunity to build it earlier.

There is little to no commercial development in the southern area AT THIS TIME. That will change as businesses see the customers and begin to move in.

Well, most of the good restaurants are closed on Monday.

Lots of great advice here. We did a lifestyle visit 3 years ago and after a few days we knew this was the place for us. Chosing the area we wanted to be in was a much tougher task.

Decide whats improtantant for you. We're in Amelia and love it here.

Every area in TV has it's pluses and minuses.
So theres no right or wrong, it's about finding the best fit for you.

Btw, it's a great time to buy. It's a buyers market, and many sellers are taking significant price reductions.

I personally went for a turnkey home. 1 year old and came fully furnished - including hand soap, extra towels, etc.

Cost barely more than a newly built one, but we did not have to enter the lottery system and hope for the best.

My biggest complaint about the new build homes is you get no choices in how it looks unless you go custom or higher. If all the Moonstones, for example,are built with dark wood flooring and cabinets, that is what you can get, no choice provided. You enter the lottery to see if you are allowed to buy the house after it is ready to move in.

The lottery is nice in that there is no bidding war that artificially inflates pricedd

Husband and I did careful analysis while we were here on Lifestyle trip. I knew the area because my parents had a seasonal home for 10 years, and my uncle lived in TV for 32 years. My husband was new to this part of Florida so it was important that he felt comfortable with it too. We looked at maybe 20 properties and then chose one. I also looked at the neighborhood, the people there and what they were interested in. It was the best decision ever. When my husband suddenly passed it was my neighbors who stepped in to help me, to find my reason to go on. I would not change my neighbors for any model of house, any view or any amenities. Now it is 6 years later and some neighbors have passed others have moved away. But the flavor of the neighborhood is the same.

People think differently. Pseudo-name NYBob. I/we are ex New Yorkers.
Imagine someone asks I want to see New York and have three days ? a week. We've been in the villages for 12 years. Far different than New York. You know you've been here a while when palm trees are normal. Weeds, not sure why,climate? We don't have dandelions.
Pigeons, I think the Hawks prevent them.
Temperature. Heat like palms becomes normal. Snow, I think it snowed once 20-30 years ago.
Assuming there is more than one of you, old school perhaps. Write on index cards what is important and then switch piles. Writing STUFF down makes people THINK clearly.
A planned community. Has plusses and minuses.
Hobbies, interests, whatever. There is likely a club for that. Where you choose. Think of what you want. Where we are, you can but walking, bike riding are limited. It is easy to talk to people. Ask several people where you are looking. Look at different times.
Florida-a lot of rain. How good does the water drain?

It would be better to visit in July if you are planning on staying year round. You have to experience Florida HEAT.

A good thing is freedom of choice. People are different. Sort of like going to a doughnut shop. Waiting on line for say 15 minutes and the person in front of you has not thought what they want and keep changing their mind. Choices? That one in the doughnut shop. When it happens may well be my wife. Artificially inflates the price? People are different. Bidding war only happens if you let it. We sold our previous home. It was an adventure.
Most people your home is the biggest buy and sell of your life. I was involved in sales. My home was the TAX on some sales. At closing the atty for the buyer was shocked. The contract was already agreed to it and he tried to change it. Someone is always in control.
My attorney who didn't care and just wanted to get it done and be paid. In public told me to give it to them. All were shocked. I publicly said, truth we have another offer, tell em we will keep the earnest money.

You/we acclimate to the heat. As I posted we are ex-New Yorkers.
I was out once and it was 20 below zero. Imagine leaving Florida in July and being somewhere that is 20 below zero. For that matter imagine Florida when air conditioning was rare.

We couldn't afford to rent for a month in one shot. We spent a 5-day vacation visiting friends from up north who'd moved recently to The Villages our first time. We did another week several years later. A couple years after that, we came down for another vacation for a week. And then we did a lifestyle visit for a few days a year later.

It wasn't until the following year that we were put in a position that we had no choice but to move out of our home of 12 years, and that's when we found our current home in The Villages, where we've been for 6 years.

I spent a summer in Plantation, Florida, in a house that had no air conditioning. It was unbearable at night because that's when the heat really settles in from the day under sunshine. During the day I spent most of my time outside, often "stealing" a space at the hotel pool at the beach (since I wasn't a paying guest) or interviewing for a job. That was when I realized in the deepest depths of my soul that I hated Florida. My opinion hasn't changed. The Villages is a great community. It's just a shame it's in Florida.