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

50 Properties Found. Page 1 of 2.
Photo of Listing #O5915631

125 Stone Hill Dr

$1,789,000
Maitland
MLS® # O5915631
8 Beds, 7 Baths, 7,914 Sf
Photo of Listing #V4917089

1061 Cottontail Ln

$1,400,000
Maitland
MLS® # V4917089
7 Beds, 7 Baths, 5,878 Sf
Photo of Listing #O5891689
Reduced 5.4%
Maitland
MLS® # O5891689
5 Beds, 5 Baths, 4,884 Sf
Photo of Listing #S5043062
Maitland
MLS® # S5043062
4 Beds, 5 Baths, 4,341 Sf
Photo of Listing #O5917257
New

900 Mcgregor Way

$759,900
Maitland
MLS® # O5917257
5 Beds, 4 Baths, 3,510 Sf
Photo of Listing #O5918247
New
Maitland
MLS® # O5918247
3 Beds, 2 Baths, 1,740 Sf
Photo of Listing #O5910656
Reduced 2%

14 Minnehaha Cir

$724,000
Maitland
MLS® # O5910656
3 Beds, 3 Baths, 2,640 Sf
Photo of Listing #T3285719
New
Maitland
MLS® # T3285719
5 Beds, 4 Baths, 3,581 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 #O5917904
New

1897 Belford Ct

$659,000
Maitland
MLS® # O5917904
4 Beds, 3 Baths, 3,013 Sf
Photo of Listing #O5897846

1 Cammack Dr

$625,000
Maitland
MLS® # O5897846
4 Beds, 5 Baths, 3,966 Sf
Photo of Listing #O5913881
Reduced 2.6%

755 Woodside Rd

$599,000
Maitland
MLS® # O5913881
3 Beds, 3 Baths, 2,881 Sf
Photo of Listing #O5913098

1151 Pryde Dr

$587,000
Maitland
MLS® # O5913098
5 Beds, 4 Baths, 3,119 Sf
Photo of Listing #O5913036

2318 Mohawk Trl

$499,000
Maitland
MLS® # O5913036
3 Beds, 2 Baths, 1,736 Sf
Photo of Listing #O5918709
New

2549 Saginaw Trl

$485,000
Maitland
MLS® # O5918709
3 Beds, 2 Baths, 1,964 Sf
Photo of Listing #O5917949
New

2136 Chinook Trl

$469,000
Maitland
MLS® # O5917949
3 Beds, 2 Baths, 1,849 Sf
Photo of Listing #O5884126
Maitland
MLS® # O5884126
4 Beds, 4 Baths, 2,233 Sf
Photo of Listing #O5913339
Reduced 0.2%

1166 Charming St

$409,000
Maitland
MLS® # O5913339
4 Beds, 4 Baths, 2,474 Sf
Photo of Listing #O5907757
Reduced 1.4%

1123 Charming St

$409,000
Maitland
MLS® # O5907757
4 Beds, 4 Baths, 2,474 Sf
Photo of Listing #O5911495
Reduced 1.3%

1147 Charming St

$379,900
Maitland
MLS® # O5911495
3 Beds, 3 Baths, 1,870 Sf
Photo of Listing #O5885287
Reduced 2.4%
Maitland
MLS® # O5885287
2 Beds, 1 Baths, 1,418 Sf
Photo of Listing #O5917982
New
Maitland
MLS® # O5917982
2 Beds, 2 Baths, 1,118 Sf
Photo of Listing #O5910512
Maitland
MLS® # O5910512
2 Beds, 2 Baths, 1,118 Sf
Photo of Listing #O5916129
Reduced 2.9%
Maitland
MLS® # O5916129
3 Beds, 3 Baths, 2,100 Sf
Photo of Listing #O5917907
New
Maitland
MLS® # O5917907
3 Beds, 3 Baths, 1,742 Sf
Photo of Listing #O5869067
Reduced 4.8%
Maitland
MLS® # O5869067
3 Beds, 3 Baths, 1,742 Sf
Photo of Listing #O5918559
New
Maitland
MLS® # O5918559
2 Beds, 2 Baths, 1,224 Sf
Photo of Listing #O5901763
Reduced 3.7%

761 Faith St

$260,000
Maitland
MLS® # O5901763
3 Beds, 1 Baths, 888 Sf
Photo of Listing #O5876723
Reduced 2.8%
Maitland
MLS® # O5876723
4 Beds, 2 Baths, 1,707 Sf
Photo of Listing #O5912584
Maitland
MLS® # O5912584
4 Beds, 2 Baths, 1,372 Sf
Photo of Listing #O5915836

1080 Hamlet Dr

$220,000
Maitland
MLS® # O5915836
3 Beds, 2 Baths, 1,150 Sf
Photo of Listing #O5911882
Reduced 2.3%
Maitland
MLS® # O5911882
3 Beds, 2 Baths, 1,739 Sf
Photo of Listing #R4903845
Reduced 14.6%

1600 Brook Dr

$199,900
Maitland
MLS® # R4903845
2 Beds, 1 Baths, 950 Sf
Photo of Listing #A4484152
Reduced 3.6%
Maitland
MLS® # A4484152
2 Beds, 1 Baths, 816 Sf
Photo of Listing #O5878453
Reduced 1.6%
Maitland
MLS® # O5878453
3 Beds, 3 Baths, 1,496 Sf
Photo of Listing #O5918278
New
Maitland
MLS® # O5918278
2 Beds, 2 Baths, 862 Sf
Photo of Listing #O5917153
Maitland
MLS® # O5917153
2 Beds, 1 Baths, 815 Sf
Photo of Listing #O5912893
Reduced 2.5%
Maitland
MLS® # O5912893
2 Beds, 2 Baths, 816 Sf
Photo of Listing #O5901281
Reduced 6.6%
Maitland
MLS® # O5901281
2 Beds, 2 Baths, 816 Sf
Photo of Listing #O5856242
Reduced 1.1%
Maitland
MLS® # O5856242
3 Beds, 2 Baths, 1,256 Sf
Photo of Listing #O5906212
Maitland
MLS® # O5906212
2 Beds, 2 Baths, 1,280 Sf
Photo of Listing #O5913857
Maitland
MLS® # O5913857
2 Beds, 2 Baths, 1,048 Sf
Photo of Listing #O5896105
Maitland
MLS® # O5896105
2 Beds, 3 Baths, 1,732 Sf
Photo of Listing #S5045288
New
Maitland
MLS® # S5045288
3 Beds, 2 Baths, 1,243 Sf
Photo of Listing #O5909049
Maitland
MLS® # O5909049
3 Beds, 2 Baths, 1,243 Sf
Photo of Listing #O5908986
Maitland
MLS® # O5908986
2 Beds, 2 Baths, 1,111 Sf
Photo of Listing #O5905498
Maitland
MLS® # O5905498
4 Beds, 3 Baths, 1,806 Sf
Photo of Listing #O5903993
Reduced 3.2%
Maitland
MLS® # O5903993
1 Beds, 1 Baths, 612 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 January 23rd, 2021 at 8:45pm EST.