Maitland sits directly north of Winter Park, and a lot of people can’t tell you where one ends and the other begins. I can, and it matters when you’re pricing a house. I’ve lived in Central Florida since 1978. My background, in one line: Over 37 years in the Real Estate Industry · licensed in Florida since 1989.

Maitland is one of the oldest incorporated towns in Central Florida. It started as Fort Maitland, an Army post on the west shore of Lake Maitland in 1838, was incorporated as the Town of Lake Maitland in 1885, and took the name Maitland under a new charter in 1959. The city puts its population at about 22,000.

Housing stock and architecture

Maitland’s housing tells the story of when the city grew.

• The historic corridor. Around Lake Lily and Lake Catherine, the city has a “historical corridor” of occupied homes from the 1880s through the early 1900s. There aren’t many, so when one is listed, it deserves a close look.
• Mid-century homes. In the 1950s, when Martin Marietta moved to Orlando, Maitland was a natural landing spot for its employees. That era left a deep supply of 1950s and 1960s ranch homes, many on generous, tree-covered lots.
• 1970s subdivisions. The city counts twelve new residential subdivisions developed between 1972 and 1979, so you’ll also find plenty of 1970s construction.
• Lakefront. Homes on Lake Maitland, Lake Sybelia and the city’s smaller lakes are priced as their own market, separate from the streets around them.

With homes from this period, roof age, electrical panels, plumbing and windows drive both insurability and price. I look at those first, because the buyer’s insurance company will.

Neighborhoods and streets

• Dommerich Estates and Dommerich Hills. Streets like Mohawk Trail and Chippewa Trail, lined with 1950s and 1960s ranches on large lots with mature trees.
• Lake Lily and downtown Maitland. The older core around City Hall on Independence Lane and Lake Lily Park on Lake Lily Drive.
• Lake Sybelia. Lakefront homes around the lake that is also home to the Audubon Center for Birds of Prey.
• Lake Maitland frontage. Maitland shares Lake Maitland with Winter Park. Whether a lot connects to the navigable Winter Park chain through the canals is a real value question, so confirm it for any specific property.

As with Winter Park, a Maitland mailing address doesn’t guarantee you’re inside Maitland city limits. Check the parcel with the Orange County Property Appraiser.

Lifestyle and amenities

• Lake Lily Park. A 10-acre park with a half-mile walking trail, boardwalk and gazebo. The Waterhouse Residence Museum, a late-1800s home, is on the grounds.
• Maitland Art Center. Founded in 1937 by artist J. André Smith, with Mayan Revival-style carved concrete and gardens. It was designated a National Historic Landmark in 2014 and is run by Art & History Museums – Maitland.
• Audubon Center for Birds of Prey. On Lake Sybelia at 1101 Audubon Way. The Florida Audubon Society was founded in Maitland.
• Enzian Theater. The independent film house at 1300 South Orlando Avenue.

Commute and getting around

• I-4 and Maitland Boulevard. The I-4 interchange at Maitland Boulevard (SR 414) was rebuilt as part of the I-4 Ultimate project. SR 414 also links west toward Apopka.
• Maitland Center. A large office park west of I-4, inside city limits, which the city traces to 226 acres developed in the late 1970s. If you work there, Maitland can mean a very short drive.
• SunRail. Maitland has its own station, between Winter Park to the south and Altamonte Springs to the north.
• U.S. 17-92. Orlando Avenue runs north-south through Maitland into Winter Park.

Working with Will in Maitland

My office is in Winter Park, a short drive down 17-92. I’ve spent years pricing houses, so when I tell you what a Maitland home is worth, I’ll show you the closed sales and the adjustments behind the number.

The short version of my credentials: 2026 RealTrends Verified, ranked #10 in Winter Park by transactions; RE/MAX Hall of Fame.

For sellers in mid-century neighborhoods, the biggest pricing question is usually whether a buyer sees your house as a renovation, a move-in, or a lot. I’ll tell you which, and what that means for your number.

Maitland FAQ

Is Maitland in Orange County or Seminole County?

The City of Maitland is in Orange County, so city homes pay Orange County property taxes and are served by Orange County Public Schools. Confirm city limits and county for any specific address.

Which schools serve Maitland?

Maitland homes are in Orange County Public Schools. Dommerich Elementary, Lake Sybelia Elementary and Maitland Middle are located in Maitland, but zoning lines change and don’t follow city limits. Verify any address with the OCPS school locator.

Are older Maitland homes hard to insure?

Not automatically, but insurers look closely at roof age and the condition of electrical, plumbing and HVAC, often through a 4-point inspection. Get an insurance quote during your inspection period, not after.

Is Maitland a separate market from Winter Park?

For pricing, yes. Comparable sales should come from the same area and housing type, and I don’t borrow Winter Park comps to price a Maitland house without adjusting for it.

What should I do before listing my Maitland home?

Get a pricing analysis based on recent Maitland closed sales, handle obvious repairs, and pull permits and roof/system ages so buyers and insurers have answers early. Start with a free home value report.

Can you help me buy in Maitland if I also have a home to sell?

Yes. We can plan the timing of both sides, including contingencies, leasebacks or a sale-first approach, based on your situation. Call or text 407-620-7785.

Call or text 407-620-7785, or get a free home value report.

Compare nearby areas

Maitland buyers usually look at Winter Park too, and sometimes Baldwin Park for newer construction close in. To the north, Longwood and Lake Mary are in Seminole County.

Curious what your Maitland home is worth?

Send me the address and I’ll put together the closed sales, the current competition and a price range that holds up.

Will LaValle, REALTOR® · RE/MAX 200 Realty · 1155 Louisiana Ave., Suite 110, Winter Park, FL 32789 · 407-620-7785 · will@irlhomes.com · FL license #3389936