Explore homes for sale in Maitland, one of Central Florida's oldest and most desirable areas. Once known as Fort Maitland, this historic city has evolved from a 19th-century rest stop to a vibrant community that attracted many during the "space age" of the 1950s. Today, Maitland real estate is highly sought after by families thanks to its welcoming neighborhoods, scenic lakes, city parks, and a growing selection of restaurants and shops near the intersection of 17-92 and Horatio Avenue. Located just minutes from downtown Orlando and nearby attractions, Maitland offers a small-town feel with big-city convenience. Work with experienced Maitland real estate agents at Fannie Hillman to explore available listings and find your ideal home in this thriving Central Florida community known as “A Community for Life”.
Maitland is one of Central Florida’s oldest cities. Sitting directly north of Orlando, it provides residents with a lifestyle that balances suburban comfort and genuine community identity. At around 21,000 residents, it is small enough to feel personal but large enough to have everything you need. Maitland has great schools, parks, arts venues, restaurants and nearly 3,000 acres of lakes and waterways. It is a place where people move and stay for decades.
The median sale price in Maitland has run around $489,000 to $650,000 over the past year, covering a wide range of property types. Condos and smaller single-family homes can be found starting in the low $200,000s, while lakefront homes, especially on Lake Maitland, start around $1.2 million and can reach $5 million or more. Standard three and four bedroom homes in established neighborhoods typically fall in the $400,000 to $700,000 range.
Maitland has one of the strongest school lineups in Orange County. Dommerich Elementary holds an A+ state rating and is consistently one of the top-rated elementary schools in the area. Students then move to Maitland Middle School and Winter Park High School with a 9/10 rating. There are also strong private options like Park Maitland School and Orangewood Christian available within the community.
Maitland is about 10 to 15 minutes from downtown Orlando via I-4, and the city has its own SunRail commuter train station for a direct rail connection that avoids highway traffic entirely. That combination of highway and rail access makes it one of the more commute-friendly locations in the metro Orlando area. You get suburban space and pace without being far from the city center.
Maitland offers a genuinely diverse housing stock. You will find 1950s and 1960s ranch homes and block houses on classic residential streets, as well as custom-built pool homes, luxury gated communities, lakefront estates, and various condominium complexes. Notable neighborhoods within Maitland include Dommerich Woods, Maitland Club, and the lakefront streets along Lake Maitland and Lake Destiny. There is something here for a wide range of budgets and lifestyles.
Yes. Maitland’s lakefront properties are some of the finest in all of Central Florida, especially those on Lake Maitland which is the largest lake in the Winter Park Chain of Lakes. Lakefront homes here typically start around $1.2 million and can run to $5 million or more for larger, fully updated estates with dock access and water views. These properties are scarce and attract serious buyer attention when they do come to market.
Top-rated schools, safe streets, abundant parks, a strong community culture make Maitland a consistently popular choice for families. Lake Lily Park is a beloved gathering spot with regular community events. The weekly farmers market and local arts programming keep residents engaged. With great schools and outdoor access all within one community, families tend to settle here for the long term.
The Maitland Art Center is a National Historic Landmark and offers galleries, classes and events throughout the year. The Enzian Theater is also one of the most beloved independent film venues in Florida. The community also hosts monthly events like Getdown Downtown and a regular farmers market at Lake Lily Park. For a city of 21,000, the cultural offering is genuinely impressive.
Maitland sits at a comfortable price point between College Park and Winter Park. You get strong schools such as Dommerich Elementary, lake access and an established neighborhood feel without paying the full Winter Park premium. It is a practical choice for buyers who want the quality of Winter Park’s lifestyle at a somewhat more accessible price.
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