Maitland Florida

Maitland, FL today is a very contemporary suburb although it has been established for much longer than many of other Florida communities. Maitland is located in Orange County between Lake Mary and Winter Park. It’s been in existence since 1838 when it was known as Fort Maitland. It was named as a tribute to Capt. William S. Maitland who was a hero in the Second Seminole War. The town burst with tourism in 1880 when a railroad from Sanford was put into place but that only lasted until 1890.

Maitland Homes for Sale

56 Properties Found. Page 1 of 2.
Photo of Listing #O5825293
Reduced 7%

520 Manor Rd

$6,975,000
Maitland
MLS® # O5825293
10 Beds, 13 Baths, 13,100 Sf
Photo of Listing #O5871258
Reduced 5.7%

70 Cypress Ln

$2,500,000
Maitland
MLS® # O5871258
5 Beds, 5 Baths, 3,874 Sf
Photo of Listing #O5859194
Reduced 4%
Maitland
MLS® # O5859194
7 Beds, 9 Baths, 7,114 Sf
Photo of Listing #O5891689
Maitland
MLS® # O5891689
5 Beds, 5 Baths, 4,884 Sf
Photo of Listing #O5881650
Reduced 3.3%
Maitland
MLS® # O5881650
4 Beds, 3 Baths, 2,942 Sf
Photo of Listing #O5883436
Reduced 0.6%

891 Cranes Ct

$835,000
Maitland
MLS® # O5883436
4 Beds, 4 Baths, 4,110 Sf
Photo of Listing #O5898395
Maitland
MLS® # O5898395
4 Beds, 4 Baths, 4,327 Sf
Photo of Listing #O5882359
Reduced 5.4%

1619 Druid Rd

$699,000
Maitland
MLS® # O5882359
5 Beds, 4 Baths, 3,825 Sf
Photo of Listing #O5757020
Reduced 3%
Maitland
MLS® # O5757020
4 Beds, 4 Baths, 2,950 Sf
Photo of Listing #O5883841
Reduced 1.5%
Maitland
MLS® # O5883841
3 Beds, 2 Baths, 2,204 Sf
Photo of Listing #O5897846
New

1 Cammack Dr

$625,000
Maitland
MLS® # O5897846
4 Beds, 4 Baths, 3,966 Sf
Photo of Listing #O5895622
Maitland
MLS® # O5895622
3 Beds, 4 Baths, 2,136 Sf
Photo of Listing #O5886204
Reduced 3.4%

624 Brookwood Ln

$575,000
Maitland
MLS® # O5886204
4 Beds, 4 Baths, 2,872 Sf
Photo of Listing #O5895610
Maitland
MLS® # O5895610
3 Beds, 4 Baths, 2,136 Sf
Photo of Listing #O5895599
Maitland
MLS® # O5895599
3 Beds, 4 Baths, 2,031 Sf
Photo of Listing #O5895614
Maitland
MLS® # O5895614
3 Beds, 4 Baths, 2,136 Sf
Photo of Listing #O5888097

2595 Modac Trl

$530,000
Maitland
MLS® # O5888097
5 Beds, 3 Baths, 2,331 Sf
Photo of Listing #O5898147

1186 Charming St

$465,000
Maitland
MLS® # O5898147
3 Beds, 4 Baths, 2,305 Sf
Photo of Listing #O5899025
New
Maitland
MLS® # O5899025
3 Beds, 2 Baths, 2,067 Sf
Photo of Listing #O5884126
Maitland
MLS® # O5884126
4 Beds, 4 Baths, 2,233 Sf
Photo of Listing #V4914367
Reduced 1.2%

457 Stonewood Ln

$400,000
Maitland
MLS® # V4914367
4 Beds, 3 Baths, 2,515 Sf
Photo of Listing #O5894395
Reduced 2.5%
Maitland
MLS® # O5894395
3 Beds, 3 Baths, 1,976 Sf
Photo of Listing #U8080426
Reduced 3%

1217 Thunder Trl

$387,950
Maitland
MLS® # U8080426
3 Beds, 2 Baths, 2,183 Sf
Photo of Listing #S5040319

916 Robinhood Ct

$379,000
Maitland
MLS® # S5040319
5 Beds, 3 Baths, 2,375 Sf
Photo of Listing #O5885287
Maitland
MLS® # O5885287
2 Beds, 1 Baths, 1,418 Sf
Photo of Listing #O5896657
Maitland
MLS® # O5896657
3 Beds, 2 Baths, 1,965 Sf
Photo of Listing #O5840353
Reduced 2.8%
Maitland
MLS® # O5840353
2 Beds, 2 Baths, 1,118 Sf
Photo of Listing #O5900003
New

375 Croton Dr

$347,000
Maitland
MLS® # O5900003
4 Beds, 3 Baths, 2,055 Sf
Photo of Listing #O5893434
Maitland
MLS® # O5893434
3 Beds, 3 Baths, 2,672 Sf
Photo of Listing #O5888534
Reduced 2.1%
Maitland
MLS® # O5888534
3 Beds, 3 Baths, 2,284 Sf
Photo of Listing #O5883624
Reduced 6%
Maitland
MLS® # O5883624
4 Beds, 3 Baths, 2,300 Sf
Photo of Listing #O5869067
Reduced 3.1%
Maitland
MLS® # O5869067
3 Beds, 3 Baths, 1,742 Sf
Photo of Listing #O5897420
New
Maitland
MLS® # O5897420
3 Beds, 2 Baths, 1,708 Sf
Photo of Listing #O5824853
Reduced 3.6%
Maitland
MLS® # O5824853
3 Beds, 2 Baths, 1,169 Sf
Photo of Listing #O5884603
Reduced 3.6%

313 Hickory Dr

$265,000
Maitland
MLS® # O5884603
3 Beds, 2 Baths, 1,114 Sf
Photo of Listing #O5899302
New

358 Sultana Ln

$260,000
Maitland
MLS® # O5899302
3 Beds, 2 Baths, 1,435 Sf
Photo of Listing #O5876723
Reduced 2.4%
Maitland
MLS® # O5876723
4 Beds, 2 Baths, 1,707 Sf
Photo of Listing #O5895558
Reduced 5.9%
Maitland
MLS® # O5895558
2 Beds, 1 Baths, 1,069 Sf
Photo of Listing #O5702701
Maitland
MLS® # O5702701
4 Beds, 2 Baths, 1,372 Sf
Photo of Listing #O5900204
New
Maitland
MLS® # O5900204
2 Beds, 3 Baths, 1,307 Sf
Photo of Listing #O5896861

1085 Hamlet Dr

$204,900
Maitland
MLS® # O5896861
3 Beds, 2 Baths, 1,076 Sf
Photo of Listing #O5895532
Maitland
MLS® # O5895532
3 Beds, 3 Baths, 1,583 Sf
Photo of Listing #O5878453
Maitland
MLS® # O5878453
3 Beds, 3 Baths, 1,496 Sf
Photo of Listing #O5894780
Maitland
MLS® # O5894780
4 Beds, 2 Baths, 1,372 Sf
Photo of Listing #O5895081
Maitland
MLS® # O5895081
3 Beds, 3 Baths, 1,486 Sf
Photo of Listing #O5856242
Reduced 3.2%
Maitland
MLS® # O5856242
3 Beds, 2 Baths, 1,256 Sf
Photo of Listing #O5896105
Maitland
MLS® # O5896105
2 Beds, 3 Baths, 1,732 Sf
Photo of Listing #O5877364
Reduced 0.6%
Maitland
MLS® # O5877364
2 Beds, 2 Baths, 1,280 Sf

The town became even more popular in 1937 when the Art Centre at Maitland was founded to house artists that could live and work within the town. The Centre is still around and can even be found on the National Register of Historic Places. The Centre holds an open-air chapel and has become a very popular venue for weddings.

It was in the 1960s that Maitland became the bedroom community that it is today. Suburbs were built here to try to accommodate young families that wanted good schools and more property than the city could provide. These enhancements were embellished in 1970 when the Maitland Centre was built. This provided the town with a strong business place as well as residential means. This huge Centre encompasses 190 acres, which houses a hotel, 45 office buildings and 400 businesses. There are still over twelve thousand employees that work there.

With the residences and the work places in place, Maitland needed a retail outlet for those that lived and worked nearby. Uptown Maitland West is currently being developed for this purpose. The project will hold retail spaces as well as a condominium. This seven-story project was placed on hold after six residents sued the city for disregarding its own guidelines. The suit was eventually thrown out and the project is now set to start development once again. Another space that is going to provide for retail stores and a condominium is Maitland Town Square. The Brossier Company is currently trying to take over from the original developer and they are working with the city to have plans approved. In addition to the retail and condominiums provided, Maitland Town Square will also be home to a city hall and a public safety complex. 

Adding to the retail and condominiums being built, The Morgan Group is also planning on building The Village at Lake Lily. This project covers nine acres and will be designated as mixed use, showcasing condominiums, apartments and 45,000 square feet of retail space.

However with all of the new developments, city officials don’t want to forget Maitland’s past. A historic corridor has been dedicated in the Lake Lily-Lake Catherine area. Here there are several homes that were built in the 1880s and through the turn of the century. There are also a number of commercial buildings from the 1880s along Maitland Avenue to pay tribute to Maitland’s past.

The city has undergone enormous changes that have enhanced the quality of life for the residents. There has been much effort on the part of the city’s planning department, residents, and business owners over the years to make this possible. There is a wide variety of real estate in Maitland from houses, to condos, to villas. The history of the City of Maitland cannot be forgotten as that is what makes this wonderful city the beauty that it is today.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on October 20th, 2020 at 7:00am EDT.