And there are no bargains right now in Freeport because all of the speculators in the area. Right now in either Walton or Okaloosa you've pretty much got to go north of I-10 in order to get affordable acreage. And whether you want to do that really depends on your tolerance for Good Old Boys and their politics since it's definitely a Good Old Boy area.
Crestview- (and Baker and Laurell Hill) everyone I know that lives up there bought there because they got 3,000 square feet and a 3/4 acre lot for $159,900 in 1999, not because there's just so much going on in Crestview. If your family is relatively self-contained, it's nice to have a bigger home than you would in the south part of the county, but you need to be okay with the idea that any external fun is going to be 45 minutes one way to Ft. Walton Beach/Destin or Pensacola. (which is actually almost quicker because it's all I-10, and Ft. Walton/Destin involves doing the 'Crestview 500' on SR 85) However, if you do want horses or other livestock on your own land, this is where you're still going to be able to find five acres for a pretty reasonable price, especially if you're willing to buy up by the state line.
South of Eglin, you can find some decent lot sizes in neighborhoods that were built between the 60s and mid-late 80s. A friend has a 70s era ranch in Niceville with a half acre lot, and that's enough space for both backyard area, and his pretty sizeable street rod workshop.
Okaloosa is largely military. Conservative, but they're usually more policy-oriented than political. I'm pretty liberal, and any time politics come up, we usually just end up agreeing to politely disagree.
There are some neighborhoods in the older part of Destin north of 98, and west of about the Back Porch that might fit your needs, but anything involving a bigger lot there is probably going to have a SoWal-like land value involved. And I'm just not big on the idea of buying a permanent primary home on a barrier island area. (why I also wouldn't buy on Okaloosa Island or in Ft. Walton/Mary Esther/Navarre south of US 98. You're going to get a full force hit from the next Big One)
Navarre- only if your commute does not involve normal rush hour hours. Traffic on 98 has more than doubled in the past 10 years while road capacity has remained the same. And it will probably continue to get worse for the next ten years until they figure out some sort of fix. The area is also a) less than 10 feet above sea level in many places and b) has many filled in wetlands. Check out the hurricane surge maps and also ask if the neighborhood flooded during the spring storms of 2005. You need to be a bit picky to make sure the neighborhood doesn't have water/drainage issues. There are plenty of nice areas there which have never had water problems, and it's great to be so close to Navarre Beach and Pensacola Beach, but best to do your homework and make sure the area you've fell in love with is one of them.
Bluewater- Bluewater proper makes up about 3/4 of the area between the Rocky Bayou and Mid-Bay Bridges, but there are also a number of smaller communities. You'd find bigger non-Bluewater lots in Raintree Estates, Brookhaven Way, and Springacres Cove off of White Point Road, some parts of Lancaster Rd. by the medical center, and the old Seminole community area. Villa Tasso has some good-sized parcels, but just across the Walton County line, and the kids could have a pretty long trip into Freeport for school because Okaloosa tends to be hit or miss about allowing waivers into Twin Cities schools because of overcrowding at the elementary and middle school levels.
