People enjoy a relaxed shopping experience and al fresco dining on 4th Street.

Lake Mary

There are rare times suburban sprawl creates a workable, livable city. Lake Mary, north of Longwood in Seminole County is one of these rare gems. Most of Lake Mary seems eerily like the vast majority of Central Florida; chains, small sidewalks and car-focused infrastructure and design. But skip down to 4th Street and you’ll see something different. Mom-and Pop-businesses, a strong sense of self and a bonded community ready to make their city one of the best. This microcosm of a main street is no less so, reveling in stability over the last two decades of intense change. 

Downtown Lake Mary presents a charming and vibrant community hub that blends small-town atmosphere with a variety of modern amenities and activities. This area is particularly known for its engaging community events, local businesses and family-friendly environment. Every Saturday morning, 4th Street hosts the Lake Mary Farmer’s Market, offering an assortment of fresh produce, flowers and handmade goods. This market not only supports local farmers and artisans but also serves as a social gathering place for the community. One of the best is the annual “Holiday in the Park” event, which features a holiday tree lighting, a winter maze and appearances by Santa and Mrs. Claus, making it a highlight for families during the holiday season. The event emphasizes community participation with activities like a toy collection drive for local schools and provides a festive atmosphere with food vendors and street performances.

People enjoy a relaxed shopping experience and al fresco dining on 4th Street.

Downtown Lake Mary’s main street is equally vibrant, with a variety of local businesses that cater to both residents and visitors. For instance, the 4th Street Bar & Grill offers a lively dining experience with its menu of American-style food and sports viewing options. This spot, along with others like Krazy Greek Kitchen and Flippers Pizzeria, provides a range of dining experiences from casual to gourmet, adding to the area’s appeal as a dining destination. 4th Street is also home to popular clothing stores Sophie & Trey and 4th & Ocean. You’ll also find Coastal Gifts & Decor (a great spot for a birthday or hostess gift) and The Olive Pantry, where locals can stock up on olive oils, sauces, cheese and so much more. 

Charming and vibrant, downtown Lake Mary blends a small-town atmosphere with modern amenities and activities. This social community takes every opportunity to gather—at events throughout the year and along the walkable 4th Street.

Homes in this area range from new developments like Griffin Park on Lake Mary Boulevard, offering a mixed-use community with apartments, townhomes and single-family homes, to communities and individual properties without homeowner’s associations. Homes on Lake Mary and Crystal Lake are particularly lovely. For those looking for a most established community, Heathrow’s gated development with a Country Club and golf course might be right for you. If money is no object, there are spectacular homes and lots on Markham Woods Road, a windy, tree-lined street that runs parallel to the Wekiva River Buffer Conservation area.  

Lake Mary’s 4th Street exemplifies a thriving community center that blends traditional charm with contemporary conveniences, making it an attractive place to call home. 

Main Street Orlando