Anyone live in Winter Garden- advice?

princesspiglet

DIS Veteran
Joined
Jul 12, 2001
So DH is active duty military and will be retiring in 3 years (when DD15 graduates high school). She plans on attending college in California and we plan on moving to Florida. DH has a degree in IT, so he will be looking for a job in the Orlando vicinity and I will be looking for something in HR. We have been scouting various communities in the Orlando area and have settled (for now) on Winter Garden. We love the look of the community and the shopping areas. We will be renting the first year and then possibly buy after.

Can anyone give me any advice on living in Winter Garden? When we move, he will be 52 and I will be 47, so we are not really into clubs or heavy night life. We love outdoor dining, "Margaritaville" style bars, laid back lifestyle. We are both divers and love to be outside biking, hiking, beaching, etc. Of course, we are both Disney fanatics and would love to be able to head to Epcot or Disney Springs for dinner and drinks whenever we feel like it. We live in a relatively small town now (Hershey, PA) and enjoy the peacefulness, but we also love having "things" close by- like sporting events, museums, shopping, etc and regularly travel to NYC, Philly and DC for the excitement- it would be great to have all those things closer than 3 hours away!

Any info or advice you can give me about Winter Garden would be greatly appreciated!!

Forgot to add- can someone let me know the best parts of Winter Garden to live in? Also, any specific apartment complexes would be great.
 
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My DD & SIL live there. They really enjoy it. They actually live just a bit to the west of the main town center. In a subdivision on Avalon Rd. Good schools system. Convenient to shopping. Publix (awesomest grocery chain ever.) is literally two minutes away. It's not overgrown and really crowded (yet). Access to DW is easy. Their house to the MK is about 25 minutes via the 429 expressway and Western Way. Closest Beach is probably Cocoa Beach to the east. Probably about 1+15 via (again) 429 and then 528 to the coast.

Unfortunately I really don't know much more than that, but it's a nice area....
 
Try to stay south of Highway 50. Old Winter Garden is north of 50 and is pretty nice, but the rest of the area is pretty dicey.

Main shopping is Winter Garden Village. New shopping is being developed in the Hamlin area, but expect Winter Garden Village to be busy until the new area is complete.

Lots of chain type restuarants...not that many small business types.

Traffic on CR535 (which runs past Winter Garden Village to the Disney area) can be very heavy early in the day and early evening. It is the best option for travel in the area. The 429 is the closet highway. The traffic can really stack up at the exit by Winter Garden Village. It is a toll road, but the easiest way to downtonw via 429/Turnpike/408 (all toll roads).

If you have specific questions, let me know. I've lived in the area for 13 years.
 
I don't live in WG but I live in a town next door. So what is it about WG that interests you? You mentioned the "look of the community"- do you mean the small downtown main street district? It's a really cute area; Plant Street Market is awesome, filled with small businesses and a brewery. There are a lot of events that take place in town; I went to their 4th of July fireworks and it was really nice. It definitely has a "small town" feel, while being very close to downtown Orlando via the 408. The West Orange Trail runs through the area and is a popular route for biking.

I'll echo Feralpeg and say that I think south of 50 (Colonial Drive) is ideal. While downtown WG is pretty, it's interspersed with some sketchy places. Unfortunately I don't know WG well enough to advise on what blocks are better than others. WG also starts to blend in with Windermere to its south and Ocoee/Gotha to the east, both of which are good areas (again, stay south of 50). Most of this part of WG/Windermere is comprised of relatively new construction, if that's your taste. Downtown Windermere and Gotha are gorgeous- stunning oak trees drape over the streets almost everywhere- but it tends to be very expensive.

I will say that our cultural amenities aren't going to rival NYC or DC, at least when it comes to museums. But we did just get a new soccer stadium and an upgraded football stadium, and the new performing arts center is top notch.
 


Hi, I don't know much about Winter Garden but my husband and I are also transplants from Hershey. We live in East Orlando about 40 minutes from Cocoa Beach and about 40 minutes from Disney. Good luck in your search!
 
Hi, I don't know much about Winter Garden but my husband and I are also transplants from Hershey. We live in East Orlando about 40 minutes from Cocoa Beach and about 40 minutes from Disney. Good luck in your search!

So what are your feelings about your move? Are you glad you did it?
 


So my DH found out there is an RV park in Winter Garden. We currently own a 5th wheel and are possibly thinking about living in that for maybe 6 months to a year until we decide on an area we like and want to put roots down, therefore skipping the apartment. Does anyone know anything about the RV park? Good/bad area? It's called "Orlando Winter Garden campground resort". TIA!!
 
I don't live in WG but I live in a town next door. So what is it about WG that interests you? You mentioned the "look of the community"- do you mean the small downtown main street district? It's a really cute area; Plant Street Market is awesome, filled with small businesses and a brewery. There are a lot of events that take place in town; I went to their 4th of July fireworks and it was really nice. It definitely has a "small town" feel, while being very close to downtown Orlando via the 408. The West Orange Trail runs through the area and is a popular route for biking.

I'll echo Feralpeg and say that I think south of 50 (Colonial Drive) is ideal. While downtown WG is pretty, it's interspersed with some sketchy places. Unfortunately I don't know WG well enough to advise on what blocks are better than others. WG also starts to blend in with Windermere to its south and Ocoee/Gotha to the east, both of which are good areas (again, stay south of 50). Most of this part of WG/Windermere is comprised of relatively new construction, if that's your taste. Downtown Windermere and Gotha are gorgeous- stunning oak trees drape over the streets almost everywhere- but it tends to be very expensive.

I will say that our cultural amenities aren't going to rival NYC or DC, at least when it comes to museums. But we did just get a new soccer stadium and an upgraded football stadium, and the new performing arts center is top notch.


We really like the small downtown main street district feel. That is what we have now and would like to keep that. We love a walkable downtown with cafes, shops, etc. I am not worried about the culture rivaling NYC or DC. We've been to both so many times that we are over it! What we really love is Disney- so that is our number one draw and will be our culture!
 
So what are your feelings about your move? Are you glad you did it?
I'm glad we moved now but it took me some time, it got better once we had a house here and started making friends. I sometimes still miss the small town feeling of Hershey/Palmyra and the season change. We live in Avalon Park, it has a nice small town feeling where you can walk to restaurants and stores. I think you have a good idea to live in your 5th wheel for a little before you decide where you want to settle - I would have picked a less populated area if I did it again but my kids had already started school which limited our choices of where to live.
 
So my DH found out there is an RV park in Winter Garden. We currently own a 5th wheel and are possibly thinking about living in that for maybe 6 months to a year until we decide on an area we like and want to put roots down, therefore skipping the apartment. Does anyone know anything about the RV park? Good/bad area? It's called "Orlando Winter Garden campground resort". TIA!!

Personally the idea of living in an RV park on Colonial sounds like a nightmare. I don't know any crime statistics but that whole stretch looks and feels very poor/run down. But maybe the park itself is nice, I'm just not sure.

Have you looked at Winter Park at all? It also has a walkable downtown main street. It's also quite a bit more cultural compared to WG. WG can definitely feel a bit country. It'll be a little further to Disney though.
 
Personally the idea of living in an RV park on Colonial sounds like a nightmare. I don't know any crime statistics but that whole stretch looks and feels very poor/run down. But maybe the park itself is nice, I'm just not sure.

Have you looked at Winter Park at all? It also has a walkable downtown main street. It's also quite a bit more cultural compared to WG. WG can definitely feel a bit country. It'll be a little further to Disney though.

DH and I played around last night on google earth checking out the RV park and you are correct- the are looks/feels very run down and dirty. We have scratched that off the list! I will have to check into Winter Park. The other campground we are looking at is a KOA called Orlando Southeast/Lake Whippoorwill- it looks much more our style.
 
I'm glad we moved now but it took me some time, it got better once we had a house here and started making friends. I sometimes still miss the small town feeling of Hershey/Palmyra and the season change. We live in Avalon Park, it has a nice small town feeling where you can walk to restaurants and stores. I think you have a good idea to live in your 5th wheel for a little before you decide where you want to settle - I would have picked a less populated area if I did it again but my kids had already started school which limited our choices of where to live.

Funny that you mention Palmyra because that is where we actually live! No one has ever heard of it before, so I usually just say Hersheybecause everyone knows that!! I know my DH will miss the season change, but we still have family and friends up here so we will be back to visit. Our child will be away at college, so thankfully we don't need to worry about schools, just what the two of us want!
 
DH and I played around last night on google earth checking out the RV park and you are correct- the are looks/feels very run down and dirty. We have scratched that off the list! I will have to check into Winter Park. The other campground we are looking at is a KOA called Orlando Southeast/Lake Whippoorwill- it looks much more our style.

That campground is in a much better area (Lake Nona).
 
Funny that you mention Palmyra because that is where we actually live! No one has ever heard of it before, so I usually just say Hersheybecause everyone knows that!! I know my DH will miss the season change, but we still have family and friends up here so we will be back to visit. Our child will be away at college, so thankfully we don't need to worry about schools, just what the two of us want!
I grew up in Hershey but we lived in Palmyra prior to moving to Orlando. I usually say Hershey too though :) We go back and visit about 2 or 3 times a year - lucky for us we are both teachers so we have the time off.
 
If you do not do the RV thing, I would really recommend renting for 6 months to a year so you can get a real feel of the areas. I know the moving part really stinks doing it twice but I believe it is the best way. When we moved from Michigan to the Orlando area back in 1984 (yikes that was a long time ago), we were looking at buying a house in a certain area that we thought was nice. We could not find a house so we rented and after living there and going through our daily routines, we ended up buying a house in a completely different area. We lived there for 18 years before moving again to the pan handle of Florida.
 

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