Maitland

Community Info

  • Price Range:
    $299,900-$12,500,000

ABOUT Maitland Florida LUXURY HOMES & Orlando REAL ESTATE INFORMATION

Why Buy a Luxury Home in Maitland Florida?

Maitland in Orlando is a modern suburb that has been around for much longer than other Florida communities. Located between Lake Mary and Winter Park it's named after Captain William S Maitland who was an American hero during the Second Seminole War. The town increased significantly in tourism in 1880 when a railroad from Sanford was open but only lasted until 1890.

Maitland is a suburb of Orlando with a population of 19,154. Maitland is in Orange County and is one of the best places to live in Florida. Living in Maitland offers residents an urban suburban mix feel, and most residents rent their homes. In Maitland there are a lot of restaurants, coffee shops, and parks.

Maitland is an incorporated town situated within Orange County, Florida boasting plenty of activities like visiting its local museums like the Mayan Revival House suitable for anyone interested in the area's history plus nearby Lake Lily Park has various events and exhibits conveniently situated close by. There are also several shopping outlets and eateries providing unique items or delicious cuisine good for anyone looking to browse around or have a meal out during their visit here! Diverse resort city - East-central Florida, about 25 miles from the Atlantic Coast

Maitland Florida also has a Sunday Farmers Market at Lake Lilly where they also hold Art and Jazz Festivals There are other events like the Enzian Theater which hosts the annual Florida Film festival, RDV Sports Complex with its own ice-skating rink, walking trails and the Audubon Bird Sanctuary.

Lake Lily is one of the most popular destinations in Maitland, Florida. This place hosts various events during weekends, such as art festivals, concerts, and more. It is surrounded by walking trails that you can enjoy during sunrise or sunset. In addition, there are
picnic tables where you can bond with friends or family while enjoying the beauty of nature.

Buying a Home in Maitland Florida is more Affordable

Maitland offers more affordability, borders Winter Park and is centrally located. Maitland Florida offers great schools, mature landscaping and beautiful established neighborhoods. Most of the properties were built in the 1970’s+ are large ranches, with sprawling mansions around the famous Lake Maitland, Lake Minnehaha, and Lake Catherine.

Currently, there are 86 Maitland single family homes on the market priced from $150,000 for a fixer upper to $4,195,000 for 1.5-acre estate on Winter Parks Chain of Lakes.

Maitland Florida does have its own library and historic museum but lacks a true town center. This is all about to change, Maitland is heading for redevelopment and developers are presenting 3 different mixed-use options for the real estate located around the old Winn Dixie store, which encompasses 18 acres.

These changes will include more residential, commercial and retails areas. Many roadways will be reconfigured, and pedestrian areas are to be added. In addition, Maitland Florida also has a new commuter Sun rail station which opened on May 1st, 2014, and was a huge success.
While living in Maitland, Florida, you can anticipate many exciting events every month that will give your stay more meaning and purpose. It hosts several events throughout the year ranging from family-friendly events that will make your stay more memorable.

Maitland Luxury Homes for Sale by Orlando Best Real Estate

Call Orlando Best Real Estate @ 407.961.8412 for Maitland Luxury Homes for Sale. We Have all the MLS Listings for Maitland Luxury Homes & the entire Orlando Area.

Orlando Luxury Homes and Communities

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
570 MANOR ROAD
 $12,500,000 6 / 7
 11,668sf Y / Y

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
360 LAKE SEMINARY CIRCLE
 $4,999,000 5 / 6
 6,466sf Y / Y
530 LAKE CATHERINE DRIVE
 $2,395,000 5 / 3
 3,456sf Y / N
105 TANGELO COURT
 $1,798,999 5 / 4
 3,203sf N / Y
755 CRANES COURT
 $1,395,500 5 / 4
 4,566sf N / Y
1256 WELLINGTON TERRACE
 $1,250,000 5 / 4
 4,280sf Y / N
791 SEQUOIA TRAIL
 $1,100,000 5 / 3
 4,144sf Y / Y
987 BRIGHTWATER CIRCLE
 $1,100,000 5 / 4
 3,270sf N / Y
751 SEQUOIA TRAIL
 $899,000 5 / 3
 3,138sf N / Y
2801 WAUMPI TRAIL
 $864,900 5 / 3
 2,836sf N / Y
2642 BROOKSIDE COURT
 $629,000 5 / 2
 2,360sf N / N
1511 GLASTONBERRY ROAD
 $565,000 5 / 3
 2,376sf N / Y

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
747 N LAKE SYBELIA DRIVE
 $3,895,000 4 / 4
 5,347sf Y / Y
1111 AUDUBON WAY
 $1,975,000 4 / 3
 3,754sf Y / N
1244 E LAKE COLONY DRIVE
 $1,895,000 4 / 5
 4,478sf Y / Y
1130 MECHANIC STREET
 $1,800,000 4 / 4
 3,567sf N / Y
873 CRANES COURT
 $1,249,900 4 / 4
 3,902sf N / Y
51 OAKLEIGH LANE
 $1,240,000 4 / 4
 4,149sf N / Y
67 CYPRESS LANE
 $1,130,000 4 / 3
 2,292sf N / N
1001 VERSAILLES COURT
 $1,050,000 4 / 3
 3,625sf N / Y
921 N THISTLE LANE
 $999,000 4 / 3
 2,300sf N / Y
1281 WELLINGTON TERRACE
 $979,000 4 / 3
 2,931sf N / N
2112 CHIPPEWA TRAIL
 $965,000 4 / 3
 2,407sf N / Y
570 DOMMERICH DRIVE
 $925,000 4 / 3
 2,956sf N / Y
320 WHITE OAK CIRCLE
 $849,000 4 / 2
 2,681sf N / Y
2514 TUSCARORA TRAIL
 $725,000 4 / 2
 3,000sf Y / Y
1511 E HORATIO AVENUE
 $719,000 4 / 3
 2,676sf N / N
1241 MANCHESTER ROAD
 $625,000 4 / 2
 2,038sf N / N
448 STONEWOOD LANE
 $624,990 4 / 3
 3,308sf N / Y
2453 WORTHINGTON ROAD
 $585,000 4 / 2
 1,959sf N / N
2570 DERBYSHIRE BOULEVARD
 $545,000 4 / 3
 1,857sf N / Y
1695 E HORATIO AVENUE
 $529,000 4 / 2
 1,939sf N / N
623 GREEN MEADOW AVENUE
 $525,000 4 / 2
 1,909sf N / Y
140 E FAITH TERRACE
 $525,000 4 / 3
 2,748sf N / N
1776 BOBTAIL DRIVE
 $524,999 4 / 3
 2,344sf N / N
1905 POINSETTA LANE
 $521,800 4 / 2
 1,864sf N / Y

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
755 WOODSIDE ROAD
 $999,999 3 / 3
 3,049sf N / Y
790 S LAKE SYBELIA DRIVE
 $960,000 3 / 2
 2,021sf Y / N
2130 DELORAINE TRAIL
 $819,000 3 / 2
 2,175sf N / Y
1761 TIPPICANOE TRAIL
 $759,000 3 / 2
 2,066sf N / N
2040 GERONIMO TRAIL
 $749,900 3 / 2
 2,375sf N / N
1741 LYNDALE BOULEVARD
 $729,990 3 / 2
 1,495sf N / N
910 GAMEWELL AVENUE
 $670,000 3 / 2
 2,214sf N / Y
140 WIGWAM PLACE
 $649,900 3 / 3
 2,236sf N / N
1750 POCAHONTAS PATH
 $639,000 3 / 2
 1,922sf N / N
502 OAK LANE
 $599,000 3 / 3
 1,966sf N / Y
9001 LAKE CHARITY DRIVE
 $575,000 3 / 2
 1,623sf N / N
1230 HOLLYRIDGE TRAIL
 $534,900 3 / 2
 1,641sf N / N
200 SPARTAN DRIVE
 $525,000 3 / 2
 1,830sf N / Y
370 SULTANA LANE
 $509,900 3 / 2
 1,683sf N / N
612 GREEN MEADOW AVENUE
 $500,000 3 / 2
 1,707sf N / N
1291 OXFORD ROAD
 $459,000 3 / 2
 1,370sf N / N
628 WOODLEY ROAD
 $429,900 3 / 2
 1,697sf N / N
601 ORANOLE ROAD
 $385,900 3 / 2
 1,950sf N / N
1033 HAMLET DRIVE
 $350,000 3 / 2
 1,146sf N / N
1074 HAMLET DRIVE
 $308,000 3 / 2
 1,076sf N / N
551 RUFFEL STREET
 $299,900 3 / 1
 1,162sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
210 ALPINE DRIVE
 $527,300 2 / 2
 1,328sf N / N
220 ALPINE DRIVE
 $427,400 2 / 1
 988sf N / N

Property Location

Community Info

  • Maitland
  • Price Range:
    $299,900-$12,500,000

© 2026 John Hernandez, Realtor ® - All Rights Reserved - Trademarks and Brands are the Property of their Respective Owners