View 1404 CARING COURT Maitland, FL MLS# G5113516
  • Recently Listed with Virtual Tour
1 of 39
$659,900
3

Beds

2.1

Baths

2,110

Sq.Ft.

1404 CARING COURT

Maitland, FL

View 1000 WINDERLEY PLACE 141 Maitland, FL MLS# O6417569
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Saturday 6/20 12:30 PM - 3:00 PM
$300,000
2

Beds

2.0

Baths

1,275

Sq.Ft.

1000 WINDERLEY PLACE 141

Maitland, FL

View 1140 S ORLANDO AVENUE H3 Maitland, FL MLS# O6415783
  • Recently Listed with Virtual Tour
1 of 47
$439,900
2

Beds

1.1

Baths

816

Sq.Ft.

1140 S ORLANDO AVENUE H3

Maitland, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1010 WINDERLEY PLACE 149 Maitland, FL MLS# O6417777
  • Recently Listed with Virtual Tour
1 of 30
$429,900
3

Beds

2.0

Baths

1,651

Sq.Ft.

1010 WINDERLEY PLACE 149

Maitland, FL

View 1911 BELFORD COURT Maitland, FL MLS# O6409794
  • Recently Listed with Virtual Tour
1 of 42
$1,125,000
4

Beds

4.0

Baths

3,314

Sq.Ft.

1911 BELFORD COURT

Maitland, FL

View 1440 LAKE SHADOW CIRCLE 8201 Maitland, FL MLS# O6416664
  • Recently Listed with Virtual Tour
1 of 45
$199,000
2

Beds

2.0

Baths

1,111

Sq.Ft.

1440 LAKE SHADOW CIRCLE 8201

Maitland, FL

View 255 W GEORGE AVENUE Maitland, FL MLS# O6415928
  • Recently Listed with Virtual Tour
1 of 77
$1,499,000
5

Beds

4.0

Baths

4,814

Sq.Ft.

255 W GEORGE AVENUE

Maitland, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1781 TONTO TRAIL Maitland, FL MLS# O6414036
  • Virtual Tour
1 of 45
$600,000
4

Beds

2.0

Baths

1,880

Sq.Ft.

1781 TONTO TRAIL

Maitland, FL

View 2491 LAUDER DRIVE Maitland, FL MLS# R4911437
1 of 21
OPEN HOUSE: Saturday 6/20 12:00 PM - 2:00 PM
$1,299,000
5

Beds

4.0

Baths

2,695

Sq.Ft.

2491 LAUDER DRIVE

Maitland, FL

View 151 WHITE OAK CIRCLE Maitland, FL MLS# O6414895
  • Recently Listed with Virtual Tour
1 of 36
$699,000
4

Beds

2.1

Baths

2,257

Sq.Ft.

151 WHITE OAK CIRCLE

Maitland, FL

View 830 LONGHAVEN DRIVE Maitland, FL MLS# O6414213
  • Virtual Tour
1 of 36
$675,000
3

Beds

2.0

Baths

2,229

Sq.Ft.

830 LONGHAVEN DRIVE

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1149 CHARMING STREET Maitland, FL MLS# O6414938
  • Recently Listed with Virtual Tour
1 of 37
$590,000
4

Beds

3.1

Baths

2,474

Sq.Ft.

1149 CHARMING STREET

Maitland, FL

Courtesy of YOUNG REAL ESTATE
View 1150 Lake Shadow Circle 3307 Maitland, FL MLS# B26040252
  • Recently Listed with Virtual Tour
1 of 27
$250,000
2

Beds

2.0

Baths

1,111

Sq.Ft.

1150 Lake Shadow Circle 3307

Maitland, FL

View RIDGEWOOD AVENUE Maitland, FL MLS# O6414703
  • Recently Listed
1 of 8
$119,900
Studio

Beds

0.0

Baths

RIDGEWOOD AVENUE

Maitland, FL

Courtesy of DABBY REAL ESTATE ADVISORS, LLC
View 2847 SHADOW VIEW CIRCLE 2847 Maitland, FL MLS# O6414837
  • Recently Listed with Virtual Tour
1 of 62
$210,000
2

Beds

2.0

Baths

1,280

Sq.Ft.

2847 SHADOW VIEW CIRCLE 2847

Maitland, FL

Courtesy of MARKET CONNECT REALTY LLC
View 908 VERSAILLES CIRCLE Maitland, FL MLS# O6413200
  • Virtual Tour
1 of 53
$899,000
4

Beds

2.0

Baths

2,151

Sq.Ft.

908 VERSAILLES CIRCLE

Maitland, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 220 ADAMS DRIVE Maitland, FL MLS# O6413737
  • Recently Listed with Virtual Tour
1 of 47
$1,995,000
4

Beds

3.1

Baths

3,005

Sq.Ft.

220 ADAMS DRIVE

Maitland, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2155 FENNELL STREET Maitland, FL MLS# S5151303
  • Recently Listed with Virtual Tour
1 of 31
$489,900
3

Beds

2.0

Baths

1,822

Sq.Ft.

2155 FENNELL STREET

Maitland, FL

Courtesy of TCA REALTY, LLC
View 206 MOSELEY AVENUE Maitland, FL MLS# O6414097
  • New Construction with Virtual Tour
1 of 20
$449,000
3

Beds

2.0

Baths

1,838

Sq.Ft.

206 MOSELEY AVENUE

Maitland, FL

View 200 MOSELEY AVENUE Maitland, FL MLS# O6413652
  • Recently Listed with Virtual Tour
1 of 25
$420,000
3

Beds

2.0

Baths

1,625

Sq.Ft.

200 MOSELEY AVENUE

Maitland, FL

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

119

Estimated median home price

$649,000
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

Price Count
$0 - 100K 0
$100K - 200K 9
$200K - 300K 16
$300K - 400K 13
$400K - 500K 13
$500K - 600K 6
$600K - 700K 11
$700K - 800K 10
$800K - 900K 6
$900K - 1M 10
$1M - Max 25

Homes for Sale by Type in Maitland, FL

Property Type Count
Single Family 71
Townhouse 9
Condo 32
Commercial 1
Rental 29
Lots and Land 4
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 6/20/2026)

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 6/20/2026.