Penny Lane

Welcome to Penny Lane

Established in 1987, Penny Lane is a well-planned gated neighborhood just a few minutes northeast from Downtown Tallahassee. As its name implies, this community is just as cheery as the famous song—here, you'll discover a mix of brick, stone, and stucco homes tucked on large lots and tree-lined streets. And with just under a dozen residences, this community feels equal parts convenient and private.

Eager to live, work, and play in Penny Lane? Let's explore!

Key Features of Penny Lane

The Homes

Penny Lane has around 10 homes total, many of which were built in the late 1980s and early 1990s. These properties boast lot sizes well over one acre, as well as stunning historic exteriors that harken to days gone by. Each home in Penny Lane is unique, but it's not uncommon to find real hardwood flooring throughout, winding staircases, as well as intricate molding and upgrades.

The Neighborhood

Featuring a gated entrance flanked by a beautifully sculpted topiary fence, Penny Lane evokes classic charm and serene privacy from the moment you drive down its namesake thoroughfare. Residents can take advantage of large lot sizes and perfectly paved streets, which set an amazing backdrop for an evening stroll. However, you'll still be just minutes away from top attractions off of Thomasville Road.

Find Homes for Sale in Penny Lane

Selling Your Penny Lane Home?

Just curious about your home's value or eager to sell? Either way, we'll use our knowledge of recent sales in your area to price your home right. Tell us about your home to get started.

Get Your Home Value!

By giving us your phone number and email address, you are giving Debbie Kirkland, Realtor permission to contact you via email, phone, or text.

The Details on Penny Lane

Shopping & Dining

Countless retail and culinary opportunities await near Penny Lane. Hop on Thomasville Road to reach Killearn Shopping Center, Carriage Gate, and Market Square—highlights include a Trader's Joe's, Gordo's North Side, and Higher Ground Bicycle Company. Residents can also reach the excitement of Downtown Tallahassee in a mere 10 minutes.


If you love spending time out in the Florida sunshine, you'll never run out of new outdoor adventures close to Penny Lane. McCord Park is a fun place for kids and pets, and Governor's Park features tons of wide-open space. If you love to hike, try planning your next route on the Miccosukee Canopy Road Greenway.

Public Schools

Children in Penny Lane are served by Leon County Schools, which educates over 33,000 students across the Tallahassee area. Currently, the neighborhood is zoned to Gilchrist Elementary, Raa Middle, and Leon High. Many graduates go on to attend Florida State University in Downtown Tallahassee, which is one of the largest colleges in the United States.

Contact the Penny Lane Real Estate Experts

Making a move in the Tallahassee area? Let us help! We at Century 21 First Story are longtime locals of the Tallahasse area, so we know it like no other! Contact us today to find out more about how we can help you find the perfect home in just the right spot.