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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

57 Properties Found. Page 1 of 2.
Photo of Listing #O6022997
Reduced 5%

155 Oakleigh Lane

$3,990,000
MAITLAND
MLS® # O6022997
4 Beds, 6 Baths, 6,926 Sf
Photo of Listing #O6071703

703 Fairoaks Lane

$1,550,000
MAITLAND
MLS® # O6071703
4 Beds, 4 Baths, 2,901 Sf
Photo of Listing #O6038921
Reduced 1.5%

91 Oakleigh Lane

$1,349,000
MAITLAND
MLS® # O6038921
4 Beds, 3 Baths, 3,713 Sf
Photo of Listing #O6071758
Reduced 7.1%
MAITLAND
MLS® # O6071758
5 Beds, 5 Baths, 4,545 Sf
Photo of Listing #O6036699
MAITLAND
MLS® # O6036699
4 Beds, 4 Baths, 2,950 Sf
Photo of Listing #O6060817
MAITLAND
MLS® # O6060817
4 Beds, 3 Baths, 2,740 Sf
Photo of Listing #O6066153
Reduced 3.6%
MAITLAND
MLS® # O6066153
4 Beds, 3 Baths, 2,404 Sf
Photo of Listing #O6061990
MAITLAND
MLS® # O6061990
3 Beds, 4 Baths, 2,373 Sf
Photo of Listing #O6070997
MAITLAND
MLS® # O6070997
4 Beds, 2 Baths, 1,832 Sf
Photo of Listing #S5077113
MAITLAND
MLS® # S5077113
4 Beds, 3 Baths, 2,200 Sf
Photo of Listing #O6065265
MAITLAND
MLS® # O6065265
3 Beds, 2 Baths, 2,069 Sf
Photo of Listing #O6072141
Reduced 1.9%
MAITLAND
MLS® # O6072141
4 Beds, 2 Baths, 2,725 Sf
Photo of Listing #O6027897
Reduced 3.7%
MAITLAND
MLS® # O6027897
3 Beds, 3 Baths, 2,523 Sf
Photo of Listing #O6056417
Reduced 5.1%
MAITLAND
MLS® # O6056417
4 Beds, 2 Baths, 2,202 Sf
Photo of Listing #O6039034
Reduced 4.2%
MAITLAND
MLS® # O6039034
4 Beds, 3 Baths, 2,368 Sf
Photo of Listing #O6054299
Reduced 0.8%
MAITLAND
MLS® # O6054299
5 Beds, 3 Baths, 2,190 Sf
Photo of Listing #O6055034
MAITLAND
MLS® # O6055034
4 Beds, 2 Baths, 1,903 Sf
Photo of Listing #O6049935
Reduced 7.6%
MAITLAND
MLS® # O6049935
4 Beds, 2 Baths, 2,510 Sf
Photo of Listing #S5071888
Reduced 2.1%
MAITLAND
MLS® # S5071888
4 Beds, 3 Baths, 2,518 Sf
Photo of Listing #O6049996
Reduced 4%

2011 Dyan Way

$575,000
MAITLAND
MLS® # O6049996
3 Beds, 3 Baths, 2,496 Sf
Photo of Listing #O6073120
MAITLAND
MLS® # O6073120
3 Beds, 3 Baths, 1,921 Sf
Photo of Listing #O6072819
Reduced 3.6%

341 Adams Drive

$530,000
MAITLAND
MLS® # O6072819
2 Beds, 1 Baths, 1,573 Sf
Photo of Listing #O5957516
MAITLAND
MLS® # O5957516
3 Beds, 2 Baths, 1,538 Sf
Photo of Listing #O6065973
MAITLAND
MLS® # O6065973
3 Beds, 2 Baths, 1,800 Sf
Photo of Listing #O6056454
Reduced 3.9%
MAITLAND
MLS® # O6056454
4 Beds, 2 Baths, 1,700 Sf
Photo of Listing #O6074559
New
MAITLAND
MLS® # O6074559
3 Beds, 2 Baths, 1,461 Sf
Photo of Listing #O6065481
Reduced 2%
MAITLAND
MLS® # O6065481
3 Beds, 2 Baths, 1,951 Sf
Photo of Listing #O6054697
Reduced 2.2%
MAITLAND
MLS® # O6054697
3 Beds, 3 Baths, 1,578 Sf
Photo of Listing #O6074009
New
MAITLAND
MLS® # O6074009
3 Beds, 2 Baths, 2,017 Sf
Photo of Listing #O6072279
Reduced 2.7%
MAITLAND
MLS® # O6072279
4 Beds, 2 Baths, 1,881 Sf
Photo of Listing #O6070934
Reduced 2.2%
MAITLAND
MLS® # O6070934
3 Beds, 2 Baths, 1,712 Sf
Photo of Listing #S5070871
Reduced 2.2%
MAITLAND
MLS® # S5070871
4 Beds, 2 Baths, 2,206 Sf
Photo of Listing #O6071613
MAITLAND
MLS® # O6071613
3 Beds, 2 Baths, 1,845 Sf
Photo of Listing #O6074503
New
MAITLAND
MLS® # O6074503
4 Beds, 2 Baths, 2,030 Sf
Photo of Listing #O6053162
Reduced 2.3%
MAITLAND
MLS® # O6053162
4 Beds, 2 Baths, 1,802 Sf
Photo of Listing #O6064047
MAITLAND
MLS® # O6064047
2 Beds, 2 Baths, 1,270 Sf
Photo of Listing #O6068421
Reduced 1.2%
MAITLAND
MLS® # O6068421
2 Beds, 2 Baths, 1,248 Sf
Photo of Listing #O6042488
Reduced 1.1%
MAITLAND
MLS® # O6042488
2 Beds, 1 Baths, 1,004 Sf
Photo of Listing #O6073003
New
MAITLAND
MLS® # O6073003
2 Beds, 2 Baths, 1,248 Sf
Photo of Listing #O6066906
MAITLAND
MLS® # O6066906
2 Beds, 2 Baths, 1,125 Sf
Photo of Listing #O6075040
New

1965 Water Lane

$309,000
MAITLAND
MLS® # O6075040
3 Beds, 2 Baths, 1,351 Sf
Photo of Listing #O6073483
MAITLAND
MLS® # O6073483
4 Beds, 2 Baths, 1,707 Sf
Photo of Listing #O6069931
MAITLAND
MLS® # O6069931
4 Beds, 2 Baths, 1,372 Sf
Photo of Listing #O6035460
MAITLAND
MLS® # O6035460
2 Beds, 3 Baths, 1,456 Sf
Photo of Listing #S5077715
New
MAITLAND
MLS® # S5077715
2 Beds, 2 Baths, 1,403 Sf
Photo of Listing #O6074703
New
MAITLAND
MLS® # O6074703
3 Beds, 2 Baths, 1,256 Sf
Photo of Listing #O6074617
New
MAITLAND
MLS® # O6074617
3 Beds, 3 Baths, 1,565 Sf
Photo of Listing #S5076534
MAITLAND
MLS® # S5076534
3 Beds, 3 Baths, 1,432 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 December 1st, 2022 at 9:04pm EST.