Maitland Real Estate

So there’s a new Foxtail in Horizon West near my house. Obviously there’s one—there’s—they’re everywhere, right? And so I’m still drinking Starbucks because they still haven’t called me to give me a sponsorship. Wasp—sorry—it was like right near you. Oh they should call me, come on call me. Anyway, it’s my ongoing… On our channel, we’ve been digging into a lot of different areas around Orlando. We’ve done Winter Park, Winter Garden, many of the main spots but there’s a lot of cool pocket cities that support some of these bigger areas. And as pricing goes up, you’re going to want to figure out what your other options are, and so today we’re getting into Maitland, Florida.

Exploring Maitland With a Local

I’m going to actually meet with one of my agent partners who lives in Maitland and talk a little bit about the town. Let’s get into it. So Lindsay, yes—where are we? We’re in Maitland, Florida here at Enzian Theatre. We’re looking at the Eden Bar—super cool place to hang out over the weekend. Actually a few people having lunch right now. Super tranquil but you’re in the middle of a bustling town. So driving around… you ready? Yeah—I didn’t hear it. Okay.

Maitland’s Neighborhood Feel

So driving around, there’s not a ton of chains—this is like this quaint kind of thing, right? Is that what Maitland is all about? Yeah, it’s definitely that neighborhood feel. You’re really close to a lot of the big attractions—only about 20 minutes to downtown, an hour to the beach, maybe 40 minutes to Disney—but it’s super quiet and really comfortable.

Why People Choose Maitland

So why Maitland? Why would people choose to live here? The proximity—minutes from popular areas like Winter Park where people are being priced out—but still within a lot of the top-rated school districts. Close to the highway, beaches, Disney, downtown. Far enough from the hustle and bustle but still convenient.

Resident Experience

So how long have you lived in Maitland? Just about a year and a half. Where were you before that? Winter Park—so just a hop, skip, and a jump away. A lot of people call about Winter Park and then find out the average price is a million dollars and look for alternatives. Maitland offered more house for the money while keeping access to the same shops, restaurants, and lifestyle.

There’s a lot of new construction, rentals, and demand—one community is right off the SunRail station, perfect for young professionals commuting downtown.

HOAs, Taxes, and Affordability

HOAs in Maitland? A lot of communities have super affordable, low HOAs. Lindsay’s community is $30 a year—just neighbors looking out for each other and planning events. Affordability comes from lower home prices, low HOAs, and in Seminole County, lower taxes.

Schools in Maitland

Schools can be confusing because Maitland covers both Orange and Seminole counties. City of Maitland is Orange County, so you get Winter Park schools. Some neighborhoods fall into Seminole. There are also many private options including Jewish Community Center programs and Orangewood Christian Academy.

Real Estate Options

Maitland offers primarily single-family homes, established townhomes, condos, and lots of rentals. New developments bring that live-work vibe with shops below and residences above. Most single-family homes are older—60s and 70s ranches with character—which many people love. Compared to Winter Park, Maitland offers similar styles but more affordability, more land, and more recent renovations for the same price point.

Winter Park mid-century ranches start in the upper $300s, while Maitland may offer similar homes already updated. High-end properties run $1–2 million depending on lakefront. Prices are rising—it’s a desirable area.

Lifestyle and Things to Do

Maitland is all about the outdoors—lakes, biking, walking paths like Lake Lily where families gather. Farmers market every week, art festivals with contemporary pieces, jewelry, and more. It’s peaceful and community-oriented.

Independence Square & Community Events

Independence Square is new in the last few years. They shut it down for street fairs and events with string lights—super cute. It’s a great community space with residences nearby and tons of restaurants. You can bring food, hang out, enjoy the park, and embrace the outdoor lifestyle. “I’m crossing the road now—how many chickens crossed?”

Wrapping Up

Thanks for taking me around your town. If somebody wants to get a hold of you to buy a house in Maitland or surrounding areas, how do they get ahold of you? “They can email me at lindsay@poseygroup.com.” Make sure you hit the subscribe button as we put out multiple videos every week about life in Central Florida. See you in the next video.