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Those are doable commutes. I would imagine anything at or under 250K is selling quickly due to the lack of affordable housing. For example, my aunt lives in the Eastside area near Ashland Elementary. The homes were mostly older small, needing rehab. For the larger rehab homes, expect to pay north of 400K, so probably not an option.
I would suggest if you do not find what you want on the south side of town, check into commutes from Woodford County (Versailles), or Scott County (Georgetown). I know Versailles is surrounded by beautiful horse country, but that makes new developments and building difficult. So prices may be inflated more than similar sized areas. Georgetown and Scott County have become popular, even with the Toyota plant just off I-75 north of town. I like it because it puts you within an hour drive of much of the Northern Kentucky area. It takes me about 1.00-1.15 hours to get down from Wilder (off I-275 east of I71/75) to the Georgetown exits. While there isn't much in between, being a little closer to a major metro like Cincinnati makes things a little easier. Think driving to a bigger airport (CVG) or major league sports (Reds and Bengals - and I guess FC Cincinnati).
Madison County (specifically Richmond) and Clark County (Winchester) are commutable options as well. Richmond seems a little further out and the Kentucky River crossing makes I-75 the main commuting route. Richmond, like Georgetown, is a decent size town and due to Eastern Kentucky University, just like Georgetown College in Georgetown, brings a little more commercial business to town than Versailles or Winchester.
Just as an FYI...
We are looking for a 3-4 bedroom, on less than an acre, around 2,000 square feet, for $250K give or take. Found some nice ones in Richmond and Winchester.
Your money will go farther in Richmond and Winchester than in Lexington, so this might be a good option. Most lots in Lexington are considerably smaller than an acre.
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