View 1291 BLESSING STREET Maitland, FL MLS# O6346774
  • Virtual Tour
1 of 34
$379,900
3

Beds

2.1

Baths

1,674

Sq.Ft.

1291 BLESSING STREET

Maitland, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 353 W LAKE FAITH DRIVE 116 Maitland, FL MLS# O6352070
$359,900
2

Beds

2.0

Baths

1,403

Sq.Ft.

353 W LAKE FAITH DRIVE 116

Maitland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1033 HAMLET DRIVE Maitland, FL MLS# O6359229
  • Virtual Tour
1 of 20
$350,000
3

Beds

2.0

Baths

1,146

Sq.Ft.

1033 HAMLET DRIVE

Maitland, FL

Courtesy of BOX REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1140 S ORLANDO AVENUE F11 Maitland, FL MLS# O6388276
  • Recently Listed with Virtual Tour
1 of 47
$349,000
2

Beds

1.1

Baths

816

Sq.Ft.

1140 S ORLANDO AVENUE F11

Maitland, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2329 SHADOW VIEW CIRCLE 2329 Maitland, FL MLS# O6295926
$320,000
3

Beds

2.1

Baths

1,583

Sq.Ft.

2329 SHADOW VIEW CIRCLE 2329

Maitland, FL

Courtesy of LPT REALTY, LLC
View 1000 WINDERLEY PLACE 239 Maitland, FL MLS# O6349726
$315,900
2

Beds

2.0

Baths

1,164

Sq.Ft.

1000 WINDERLEY PLACE 239

Maitland, FL

Courtesy of GALLERY PROPERTIES INTERNATIONAL
View 1074 HAMLET DRIVE Maitland, FL MLS# O6331672
  • Virtual Tour
1 of 20
$308,000
3

Beds

2.0

Baths

1,076

Sq.Ft.

1074 HAMLET DRIVE

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 860 Town CIRCLE #119 Maitland, FL MLS# O6183646
$295,000
3

Beds

3.0

Baths

1,575

Sq.Ft.

860 Town CIRCLE #119

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 824 TOWN CIRCLE 101 Maitland, FL MLS# O6384312
  • Recently Listed
1 of 28
$269,990
3

Beds

2.1

Baths

1,565

Sq.Ft.

824 TOWN CIRCLE 101

Maitland, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View MECHANIC STREET Maitland, FL MLS# O6269001
$265,000
Studio

Beds

0.0

Baths

MECHANIC STREET

Maitland, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 335 W LAKE FAITH DRIVE S Maitland, FL MLS# O6351302
$260,000
2

Beds

2.1

Baths

1,456

Sq.Ft.

335 W LAKE FAITH DRIVE S

Maitland, FL

Courtesy of GATE PROPERTIES & MANAGEMENT INC
View 1130 MECHANIC STREET Maitland, FL MLS# O6379054
  • Virtual Tour
1 of 22
$250,000
Studio

Beds

0.0

Baths

1130 MECHANIC STREET

Maitland, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 602 VILLA CIRCLE 543 Maitland, FL MLS# O6379401
  • Virtual Tour
1 of 31
$249,000
3

Beds

2.0

Baths

1,256

Sq.Ft.

602 VILLA CIRCLE 543

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1140 S ORLANDO AVENUE E13 Maitland, FL MLS# O6381561
$245,000
2

Beds

1.0

Baths

816

Sq.Ft.

1140 S ORLANDO AVENUE E13

Maitland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1175 LAKE SHADOW CIRCLE 4308 Maitland, FL MLS# O6361097
$239,000
4

Beds

2.0

Baths

1,372

Sq.Ft.

1175 LAKE SHADOW CIRCLE 4308

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1550 GULFVIEW DRIVE 444 Maitland, FL MLS# O6384698
  • Recently Listed with Virtual Tour
1 of 30
$239,000
3

Beds

3.0

Baths

1,328

Sq.Ft.

1550 GULFVIEW DRIVE 444

Maitland, FL

Courtesy of FUN HOMES
View 1503 GROVE STREET 559 Maitland, FL MLS# O6342190
$237,900
3

Beds

2.0

Baths

1,256

Sq.Ft.

1503 GROVE STREET 559

Maitland, FL

Courtesy of DABBY REAL ESTATE ADVISORS, LLC
View 1175 LAKE SHADOW CIRCLE 4302 Maitland, FL MLS# O6371635
$227,000
4

Beds

2.0

Baths

1,372

Sq.Ft.

1175 LAKE SHADOW CIRCLE 4302

Maitland, FL

Courtesy of COLDWELL BANKER REALTY
View 1325 LAKE SHADOW CIRCLE 12202 Maitland, FL MLS# O6373693
$225,000
2

Beds

2.0

Baths

1,111

Sq.Ft.

1325 LAKE SHADOW CIRCLE 12202

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2837 SHADOW VIEW CIRCLE 2837 Maitland, FL MLS# O6382993
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 3/14 11:00 AM - 1:00 PM
$225,000
2

Beds

2.0

Baths

1,280

Sq.Ft.

2837 SHADOW VIEW CIRCLE 2837

Maitland, FL

Courtesy of COLDWELL BANKER REALTY

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

99

Estimated median home price

$595,000
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 7
$200K - 300K 17
$300K - 400K 10
$400K - 500K 6
$500K - 600K 10
$600K - 700K 7
$700K - 800K 9
$800K - 900K 4
$900K - 1M 6
$1M - Max 23

Homes for Sale by Type in Maitland, FL

Property Type Count
Single Family 45
Townhouse 6
Condo 37
Commercial 3
Rental 23
Lots and Land 6
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 3/10/2026)

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 3/11/2026.