View 1776 BOBTAIL DRIVE Maitland, FL MLS# G5110747
  • Virtual Tour
1 of 42
$519,999
4

Beds

3.0

Baths

2,344

Sq.Ft.

1776 BOBTAIL DRIVE

Maitland, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 2112 CHIPPEWA TRAIL Maitland, FL MLS# O6394702
  • Virtual Tour
1 of 63
$965,000
4

Beds

3.1

Baths

2,407

Sq.Ft.

2112 CHIPPEWA TRAIL

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1000 WINDERLEY PLACE 239 Maitland, FL MLS# O6395472
$299,000
2

Beds

2.0

Baths

1,164

Sq.Ft.

1000 WINDERLEY PLACE 239

Maitland, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 551 RUFFEL STREET Maitland, FL MLS# S5146986
  • Virtual Tour
1 of 15
$299,900
3

Beds

1.1

Baths

1,162

Sq.Ft.

551 RUFFEL STREET

Maitland, FL

Courtesy of RESIDENTIAL MATCHMAKERS LLC
View 1166 N LAKE SYBELIA Maitland, FL MLS# O6411525
  • Recently Listed with Virtual Tour
1 of 71
$3,100,000
6

Beds

4.1

Baths

5,355

Sq.Ft.

1166 N LAKE SYBELIA

Maitland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1010 WINDERLEY PLACE 127 Maitland, FL MLS# O6395028
$332,500
3

Beds

2.1

Baths

1,563

Sq.Ft.

1010 WINDERLEY PLACE 127

Maitland, FL

Courtesy of DON HARKINS REALTY LLC
View 210 ALPINE DRIVE Maitland, FL MLS# O6395056
  • Virtual Tour
1 of 13
$527,300
2

Beds

2.0

Baths

1,328

Sq.Ft.

210 ALPINE DRIVE

Maitland, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 1440 LAKE SHADOW CIRCLE 8305 Maitland, FL MLS# O6397395
$190,000
2

Beds

2.0

Baths

1,048

Sq.Ft.

1440 LAKE SHADOW CIRCLE 8305

Maitland, FL

Courtesy of INNOVATIVE REALTY, LLC
View 1750 POCAHONTAS PATH Maitland, FL MLS# O6394358
$639,000
3

Beds

2.0

Baths

1,922

Sq.Ft.

1750 POCAHONTAS PATH

Maitland, FL

Courtesy of COMPASS FLORIDA LLC
View 873 CRANES COURT Maitland, FL MLS# O6394418
  • Virtual Tour
1 of 36
$1,249,900
4

Beds

4.0

Baths

3,902

Sq.Ft.

873 CRANES COURT

Maitland, FL

Courtesy of CREEGAN GROUP
View 1140 S ORLANDO AVENUE F8 Maitland, FL MLS# O6392367
$469,900
2

Beds

2.0

Baths

816

Sq.Ft.

1140 S ORLANDO AVENUE F8

Maitland, FL

Courtesy of HAMILTON GROUP REALTY
View 1100 S ORLANDO AVENUE 306 Maitland, FL MLS# O6392583
$649,000
2

Beds

2.0

Baths

1,125

Sq.Ft.

1100 S ORLANDO AVENUE 306

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1000 S ORLANDO AVENUE B25 Maitland, FL MLS# O6391679
$332,500
2

Beds

2.0

Baths

952

Sq.Ft.

1000 S ORLANDO AVENUE B25

Maitland, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1610 LYNDALE BOULEVARD Maitland, FL MLS# G5109784
$1,021,000
4

Beds

3.1

Baths

2,598

Sq.Ft.

1610 LYNDALE BOULEVARD

Maitland, FL

Courtesy of CAPITAL EQUITY REAL ESTATE CO
View 103 WHITECAPS CIRCLE Maitland, FL MLS# O6382220
  • New Construction
1 of 10
$2,000,000
5

Beds

4.1

Baths

3,695

Sq.Ft.

103 WHITECAPS CIRCLE

Maitland, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2040 GERONIMO TRAIL Maitland, FL MLS# O6390221
$749,900
3

Beds

2.0

Baths

2,375

Sq.Ft.

2040 GERONIMO TRAIL

Maitland, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 320 WHITE OAK CIRCLE Maitland, FL MLS# O6390473
$825,000
4

Beds

2.0

Baths

2,681

Sq.Ft.

320 WHITE OAK CIRCLE

Maitland, FL

Courtesy of OVERSTREET REAL ESTATE INC
View 535 PAWNEE TRAIL Maitland, FL MLS# O6389344
  • Virtual Tour
1 of 60
$918,000
4

Beds

3.0

Baths

2,500

Sq.Ft.

535 PAWNEE TRAIL

Maitland, FL

Courtesy of BHHS FLORIDA REALTY
View 1135 THUNDER TRAIL Maitland, FL MLS# O6385581
  • Virtual Tour
1 of 31
$850,000
5

Beds

2.2

Baths

2,966

Sq.Ft.

1135 THUNDER TRAIL

Maitland, FL

Courtesy of DALTON WADE INC
View 1501 DRUID ISLE ROAD Maitland, FL MLS# O6389520
$824,000
3

Beds

2.0

Baths

3,000

Sq.Ft.

1501 DRUID ISLE ROAD

Maitland, FL

Courtesy of LAKEFIELD REALTY GROUP LLC

About Maitland

Known for its natural beauty, crystal lakes, fine museums, art center, and civic center, the community of Maitland chose "Partners in Progress through Participation" for its motto. The town is justly proud of its recognition as one of the top neighborhoods in Central Florida.  The city has welcomed a number of corporations and businesses as well as residential growth in recent decades.  The handsome Maitland Center is now one of the largest office parks in the entire region, home to an impressive number of Fortune 500 companies.  Civic pride and a commitment to preserving a high quality of life are evident throughout the community.  The town is constantly investing in renovations that balance the preservation of historic sites with the creation of a progressive, modern atmosphere. Parks accented with brick sidewalks and streetscape beautification like decorative crosswalks abound.  The local Cultural Corridor provides an array of events and performances.  Many of the region's most popular festivals occur at the local Enzian Theatre, a premier venue for independent and art films.

Listings in Maitland, FL

112

Estimated median home price

$652,000
Maitland FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Maitland, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Maitland, FL.

Homes for Sale by Price in Maitland, FL

PriceCount
$0 - 100K0
$100K - 200K7
$200K - 300K15
$300K - 400K15
$400K - 500K11
$500K - 600K5
$600K - 700K8
$700K - 800K9
$800K - 900K9
$900K - 1M11
$1M - Max22

Homes for Sale by Type in Maitland, FL

Property TypeCount
Single Family66
Townhouse7
Condo33
Commercial1
Rental31
Lots and Land3
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 6/7/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. 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.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 6/8/2026.