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North Triplet Lake from Secret Lake Park in Casselberry, Florida

Real Estate Agent in Casselberry, FL

Casselberry is a Seminole County city north of Winter Park, laid out around US 17-92 and SR 436 and dotted with more than thirty lakes and ponds, the largest of which is Lake Howell. Buyers here tend to be relocating families and move-up owners who want an established, mid-priced neighborhood between Orlando and the Seminole County job centers, plus investors who like the older homes and condos along the main roads.

Photo: Seldom4, public domain

Lakes, Ferneries and Two Main Roads

Casselberry grew out of the ferneries of Fern Park and was incorporated in 1940 under Hibbard Casselberry, who laid out the early town around the Triplet Chain of Lakes, where City Hall still sits. US 17-92 runs north to south through the city, and SR 436 (Semoran Boulevard) crosses it at a flyover interchange. Red Bug Lake Road begins at SR 436 and runs east toward Oviedo, while Howell Branch Road and Winter Park Drive carry local traffic south toward Winter Park.

Lake Howell is the largest lake, with Lake Kathryn and Lake Concord among the others. The city maintains seventeen parks, including Secret Lake Park, Lake Concord Park with the Casselberry Art House, Wirz Park and its trail, Lake Hodge Park and Red Bug Lake Park, and the Casselberry Golf Club is inside the city.

The Investor Case in Casselberry

Casselberry’s housing is mostly single-family homes from the 1950s through the 1980s on quiet streets between the lakes, often without an HOA, along with condo and townhome communities along US 17-92, SR 436 and Red Bug Lake Road, some duplexes and a few newer infill subdivisions. Prices tend to run below neighboring Winter Park and Maitland, so value-minded buyers and landlords look here first.

Renters are typically staff at the AdventHealth hospitals in Altamonte Springs and Winter Park, workers in the offices and retail on SR 436, and households who want Seminole County at a lower entry price. Older homes mean roofs, plumbing and wiring deserve careful inspection, and lakefront lots raise flood insurance questions. Rental and short-term rental rules differ between the city, Seminole County and any HOA, so confirm them for the specific property before you buy.

Getting Around and Settling In

Casselberry commuters reach downtown Orlando by US 17-92 or by I-4 from Altamonte Springs or Maitland, and reach the airport and east Orlando by SR 436, which also connects to SR 408. Red Bug Lake Road leads east to the SR 417 toll road at Oviedo, for Lake Mary, Sanford and the UCF area. SunRail stations in Altamonte Springs, Maitland and Winter Park are close by.

Life here runs at neighborhood scale: lake parks, art events at Lake Concord Park, the trail at Wirz Park, the golf course, and the shopping strips on SR 436 and US 17-92, with Park Avenue and Uptown Altamonte a short drive away. Families ask us about Seminole County public schools, and we send them to the district’s attendance zone lookup for the exact address, since zones can change street by street.

Explore Homes in Casselberry

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Frequently Asked Questions

Why is Casselberry often less expensive than Winter Park and Maitland?

The housing stock is the main reason. Casselberry is largely mid-century single-family homes and 1970s and 1980s condos, with fewer lakefront estates, no walkable shopping street of its own and less teardown-and-rebuild activity than its neighbors. For many buyers that trade-off is the point: a Seminole County address and a lake nearby at a lower entry price, with Winter Park a few minutes south.

Does Casselberry have a downtown?

Not a traditional one. The civic center of the city is around Triplet Lake Drive and Lake Concord Park, where City Hall and the Casselberry Art House sit, and most shopping and dining lines SR 436 and US 17-92. Residents who want a walkable street go to Park Avenue in Winter Park or Uptown Altamonte, both a short drive away.

What should I know before buying an older home in Casselberry?

Plan on a thorough inspection plus the four-point and wind mitigation inspections insurers ask for on older houses, since roof age, wiring and plumbing can affect both the price and the ability to get coverage. On lake lots, check the flood zone and whether an elevation certificate exists. We build those checks into the contract timeline so there are no surprises after closing.

Thinking about Central Florida, as an investment or as home? Let’s talk, in English or Spanish.

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