Arguably some of the most coveted historical neighborhoods in Lexington, Ashland Park and Chevy Chase are synonymous with those quiet and quaint small-town vibes. Residents enjoy leisurely strolls and brisk bike rides to local shops, while enjoying close proximity to Lexington's bustling downtown. Fun fact: Ashland Park was recently named the No. 7 most luxuriously landscaped neighborhood in the US.

Need to know

You’re not the only one with your eyes set on Chevy Chase + Ashland Park. The few homes that hit the market in the area — there were only three in February 2025 — sell in ~124 days. Wondering why? Chevy Chase is known for its blend of things to do for families + college students alike, walkability, and top-ranked elementary and high schools.

The early days

In the early 1800s, Chevy Chase + Ashland Park were one in the same. Both were a part of the 600-acre, all-encompassing estate of statesman Henry Clay. It wasn’t until the 1920s that Henry Clay Simpson, a direct descendant of Clay, founded Chevy Chase. Unfortunately (or fortunately?) the area is not named for the well-known comedian + actor, but for a Maryland golf club Simpson once belonged to.

Completed in the 1930s, Ashland Park is listed on the National Register of Historic Places and home to Ashland, the Henry Clay Estate. Today, the neighborhood is home to one Lexington's oldest businesses, Oram's Florist.

"Catalpa Rd at Golden Hour" | Photo submitted by Sydney C

Can’t miss

You can't visit the area without taking a stroll through the picturesque streets of Ashland Park. Take a break from your walk to grab lunch at the Ginkgo Tree Cafe located at the park. If you're there in the fall when the restaurant is closed, the actual ginkgo trees on Catalpa Road will more than make up for it. Plus, the smell might deter the hunger pangs.

For a more lively atmosphere, venture to the main strip — Euclid Avenue — to sip on a White Russian at Charlie Brown's or brave the stage for karaoke at LEX's oldest dive bar, Chevy Chase Inn. A quick bike ride to Romany Road will take you to other classic neighborhood spots like A.P. Suggins, The Tulip Bistro & Bar, and Wheeler Pharmacy — famous for their malts + milkshakes.

Peggy's has a variety of gifts in all price ranges. | Photo by The LEXtoday

Shop

Whether you're shopping for a gift for yourself or your pup, there's plenty of local spots nestled in the neighborhood.

Worlds Apart + Peggy's are Lexington staples for all things gifts and home decor.
If you're in the market for a new outfit, pop Monkee's for the latest styles clothing and accessories.
Get off on the right foot for all your fitness needs at John's Run/Walk Shop. Bonus: This local spot hosts a weekly run club + sponsors numerous races.
Happy hour isn't just for the humans. Pet Wants hosts yappy hour for the fur babies from 4 p.m. until closing time, giving you buy-one-get-one half off chew bar treats.

Ain't no party like a Chevy Chase Street party. | Photo by @nickgerlich

Eat + Drink

There's no shortage of flavorful local stops from our neighbors in the 40502.

Get your breakfast favorites seven days a week at Josie's, or sip a specialty brunch cocktail al fresco at the cozy Bella Cafe & Grill.
Discover dishes with a Cajun twist from Bourbon n' Toulouse or get a taste of Greek food at Athenian Grill. City Editor Sam can't get enough of the baklava.
For fans of the sudsy stuff, Beer Trappe has you covered with 500+ varieties of bottles, cans, and brews on tap.
Sushi lovers will not be disappointed with creative rolls + sake options at Omakase.

Entertainment

If you've fueled up and shopped til you're about to drop, here are a few other area attractions.

Satisfy your sweet tooth + enjoy the cozy atmosphere with a pastry and latte from Brevede.
Break a sweat at area studios including Creative Yoga, LEX Method, and Pure Barre.

Getting around

These two neighborhoods are arguably some of the easiest neighborhoods in LEX to get your scoot, skate, or bike on. They are close to essential businesses like dry cleaners, a hardware store, and grocery. In fact, Ashland Park is the fifth most walkable neighborhood in our city.

Where to live

It’s time to move quick. This area is so popular, houses sell within weeks. If you’re sold + looking to buy a home in the area, here are some of the current housing options on the market…for now:

Experience timeless charm with modern luxury, 236 Clay Ave. | $1.67 million | This home is currently undergoing a full renovation to "honor the past" while offering the latest in comfort and amenities.
Live a life of leisure in this palace, 1175 Mooreland Dr. | $2.19 million | Featuring a formal dining + living rooms, a great room with wet bar, and finished walk-out basement, this home is ready to host banquets, balls, and galas.