6 Wallet-Friendly Small Towns To Retire In Kentucky
Retirement brings many changes to life, and while many soon-to-be retirees celebrate the freedom and opportunities retirement brings, this new chapter also may bring uncertainties, especially those moving from familiar homes and starting fresh. As such, finding a wallet-friendly place to settle down is often a priority, but Kentucky has you covered.
While it’s often called “the Derby state,” you don’t have to race about to afford living in many of Kentucky’s charming small towns. These petite jewels shine brightly due to their close proximity to gorgeous natural landscapes, historic highlights, and unique quirks. Many homes are affordable, especially when the median trends below Kentucky’s already amazing median sales price, which has recently been in the low- to mid $200,000s.
London

You don’t have to cross the Atlantic to find a little adventure to liven up this new chapter of your life, nor do you need to break the bank; London, Kentucky offers an exciting, wallet-friendly base camp for your adventures. Southeast of Louisville and Just north of the Tennessee border, London’s median sales price of $184,084 makes finding a new home inexpensive, and there’s plenty of excitement to be found.
London is near a variety of natural wonderlands, including the Daniel Boone National Forest. This gorgeous forest covers over 700,000 acres of beautiful forests and contains over 600 miles of trails, so you’ll have plenty to keep you busy and surrounded by beauty without making you dip into your wallet too heavily.

For those hoping to be “gone fishing” for a large part of their retirement, the forest is home to Laurel River Lake. This cliff-lined lake is filled with fish from Black Bass to catfish, making it convenient for a fishing frenzy. And if you want to take a snack into the woods, or just to your breakfast table, London Kentucky is blessed with the Bluegrass Baker. Offering fresh-made baked goods and hand-dipped ice cream, so you’ll never have to look hard at their varied menu to find something tasty.
Horse Cave

There are dozens of jokes about desperate retirees saving money by living in a cave, but there’s one cave in Kentucky where you will save money: Horse Cave. This small town of just over 2,000 residents south of Louisville has a real estate median sales price of only $168,243, over $50,000 below Kentucky’s median sales price, making a new home very affordable for retirees.
Horse Cave is named after a cave historically used by settlers, known as Hidden River Cave. This astonishing cave, located just off Main Street in the historic downtown, is open to visitors, giving you an excellent and inexpensive way to avoid the heat on warm summer days, and includes more adventurous options for retirees looking for a more challenging engagement.

Looking for less subterranean exploits? Horse Cave is also home to a good supply of antique stores such as Hidden River Treasures. This sweet little store has a wide variety of vendors and is perfect for anyone seeking hard-to-find collectibles, antiques, or a nice conversation piece without breaking their wallet’s heart.
Another unique aspect of Horse Cave is its connection to the Amish community, which includes several shops and eateries. A prime example which might bring retirees back to their youth is the Detweiler’s Country Store. Offering both hand-made Amish furniture and sandwiches served on home-made bread, this old-fashioned favorite is family-owned and perfect for retirees settling into a new space.
Corbin

Kentucky has always had a unique place in America’s history of industry, but that doesn’t mean you need to be a Rockefeller to afford a piece of it. Corbin, located south of Lexington, has a median house sales price of $266,750, according to Zillow, and it has a rather unique claim to fame as the birthplace of Kentucky Fried Chicken (the franchise, not the actual food.) Corbin was home to the first restaurant opened in 1940 by Colonel Harland David Sanders, the founder of KFC. At the Sanders Café and Museum, visitors can see and eat at this restored restaurant and see artifacts from the colonel’s life, taking retirees back in time.
Those wanting to use their retirement to get some distance from the hustle of industry, Corbin has the Cumberland Falls State Park, home to the “Niagara Falls of the South.” Retirees can always find something to do that’s wallet-friendly in the park, from breathing in the awe-garnering, sixty-eight-foot-tall waterfall which gives the park its name to exploring the historical sites in the park such as a 1937 fire tower, and even mining for gemstones and fossils. Retirees who want to give their inner child some long-deserved freedom, the Pinball Museum of Corbin is a groovy way to spend an afternoon. It’s a perfect place to reach for that high score you had in your youth on any of their machines, which date from the 1960s through to today.
Hodgenville

The birthplace of President Lincoln needs little introduction, but Hodgenville, Kentucky offers more than just its history to potential residents. Besides its median sales price of $218,755, Hodgenville offers retirees excitement which comes to them and doesn’t dig into their wallet too heavily.
History buffs will enjoy spending their newfound leisure time at the various Lincoln sites both in Hodgenville and nearby, with the perfect starting point being the Lincoln Museum. This downtown-historic-district darling uses life-size dioramas, wax figures, and various other memorabilia to give visitors an up-close look at the various events of Lincoln’s life.
If you’d rather have your retirement a little bit louder, Hodgenville has many music festivals and live shows, including the Bluegrass State’s longest-running live show at the Lincoln Jamboree. This theater not only offers varied and incredibly talented performers ranging from national favorites to local legends every night of the week but also hearty home-style meals from the in-house Kentucky’s Finest restaurant, including a classic fried chicken lunch every Sunday.
Middlesboro

Retirees looking for a wallet-friendly place to spend their retirement often look for relaxing recreational activities which won’t break the bank, and Middlesboro more than meets the requirements. This small town less than an hour north of the Tennessee border is a “boom town” in multiple senses of the word, as not only was Middlesboro a boom town, but it’s also built in the impact crater of a late-Mesozoic meteorite!
Middlesboro’s median sales price is $193,983, according to Zillow; this is lower than the state median. A classic retiree recreation, golf is a very viable and affordable pastime in Middlesboro, which is home to the Middlesboro Country Club. Having provided golfers with a beautiful course since 1889, it claims to be the oldest continuously played golf course in the US. Middlesboro is also adjacent to the Cumberland Gap National Historic Park.
Home to the pass through which at least 300,000 pioneers passed through, this scenic park is home to breathless overlooks and even the Hensley settlement, a preserved 1900s Appalachian village. Finally, those looking for a good place to meet friends for a special meal, Shades Café and Steakhouse offers Middlesboro residents delicious food, live music, and scenic views of the heart of Middlesboro’s historic downtown.
Prestonsburg

Deep in the heart of eastern Kentucky, Prestonsburg offers retirees both an affordable place to settle down, with a median sales price currently in the low $200,000s and a rich atmosphere built form the town’s history. Prestonsburg’s history gives it an atmosphere for retirees to immerse themselves in as deeply as they wish. For instance, those looking for some excitement or even a new hobby can look into Civil War reenactment. Middle Creek National Battlefield was the site of a significant Civil War battle in 1862, where future President James A. Garfield served as a Union officer.
Another Prestonsburg historic hot spot is Butcher Hollow, childhood home to music legend Loretta Lynn. Visitors can tour not only the Webbs general store which appeared in Coal Miner’s Daughter, a movie based on Lynn’s life, but also the mountain cabin where Lynn grew up with her siblings, including fellow country music sensation Crystal Gayle.

Retirees who’d rather focus on modern music will find it in the Mountain Arts Center. Also known as the MAC, this facility has a theater with seating for 1,000, an art gallery, and more. The MAC has hosted countless music stars of national acclaim and ensures any retirees in the Star City of East Kentucky will never be lacking for music.
For retirees looking to settle down somewhere new without having to worry about wiping out their savings, many of Kentucky’s small towns offer inexpensive real estate. The Bluegrass State’s vibrant history, countless country music legends, and diverse offerings of dining options make these towns perfect places to start your twilight years. The many small towns of Kentucky are affordable and offer retirees ways to stay engaged and active while still being wallet friendly, and the communities will be just as friendly to new residents.