View 1000 S ORLANDO AVENUE A31 Maitland, FL MLS# O6342920
$360,000
2

Beds

2.0

Baths

952

Sq.Ft.

1000 S ORLANDO AVENUE A31

Maitland, FL

Courtesy of COMPASS FLORIDA LLC
View 353 W LAKE FAITH DRIVE 116 Maitland, FL MLS# O6352070
  • Virtual Tour
1 of 38
OPEN HOUSE: Saturday 1/24 12:00 PM - 2:00 PM
$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 D4 Maitland, FL MLS# O6368517
$345,000
2

Beds

1.0

Baths

816

Sq.Ft.

1140 S ORLANDO AVENUE D4

Maitland, FL

Courtesy of DREAMLAND REALTY
View 1000 WINDERLEY PLACE 142 Maitland, FL MLS# O6372212
  • Recently Listed with Virtual Tour
1 of 52
$325,000
3

Beds

2.0

Baths

1,538

Sq.Ft.

1000 WINDERLEY PLACE 142

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY 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 1000 WINDERLEY PLACE 222 Maitland, FL MLS# O6353306
$309,000
2

Beds

2.0

Baths

1,164

Sq.Ft.

1000 WINDERLEY PLACE 222

Maitland, FL

Courtesy of TRUST EQUITY GROUP LLC
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 2824 SHADOW VIEW CIRCLE 2824 Maitland, FL MLS# O6367907
$270,000
3

Beds

2.1

Baths

1,583

Sq.Ft.

2824 SHADOW VIEW CIRCLE 2824

Maitland, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 335 W LAKE FAITH DRIVE S Maitland, FL MLS# O6351302
  • Virtual Tour
1 of 45
OPEN HOUSE: Saturday 1/24 12:00 PM - 2:00 PM
$269,900
2

Beds

2.1

Baths

1,456

Sq.Ft.

335 W LAKE FAITH DRIVE S

Maitland, FL

Courtesy of GATE PROPERTIES & MANAGEMENT INC
View 920 PARK LAKE CIRCLE 36 Maitland, FL MLS# O6359166
$269,000
3

Beds

2.1

Baths

1,486

Sq.Ft.

920 PARK LAKE CIRCLE 36

Maitland, FL

Courtesy of EXP REALTY LLC
View 1000 WINDERLEY PLACE 128 Maitland, FL MLS# O6358225
$267,900
2

Beds

2.0

Baths

1,275

Sq.Ft.

1000 WINDERLEY PLACE 128

Maitland, FL

Courtesy of DOVER INTERNATIONAL CO., INC.
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 806 TOWN CIRCLE 156 Maitland, FL MLS# O6359799
$258,000
3

Beds

3.0

Baths

1,575

Sq.Ft.

806 TOWN CIRCLE 156

Maitland, FL

Courtesy of WATSON REALTY CORP
View 1325 LAKE SHADOW CIRCLE 12202 Maitland, FL MLS# O6373693
  • Recently Listed with Virtual Tour
1 of 32
$250,000
2

Beds

2.0

Baths

1,111

Sq.Ft.

1325 LAKE SHADOW CIRCLE 12202

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1503 GROVE STREET 559 Maitland, FL MLS# O6342190
    1 of 25
    OPEN HOUSE: Sunday 1/25 12:00 PM - 3:00 PM
    $249,000
    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 4105 Maitland, FL MLS# O6359268
    $248,000
    3

    Beds

    2.0

    Baths

    1,243

    Sq.Ft.

    1175 LAKE SHADOW CIRCLE 4105

    Maitland, FL

    Courtesy of FLORIDA REALTY INVESTMENTS
    View 1175 LAKE SHADOW CIRCLE 4302 Maitland, FL MLS# O6371635
    • Recently Listed with Virtual Tour
    1 of 29
    $245,000
    4

    Beds

    2.0

    Baths

    1,372

    Sq.Ft.

    1175 LAKE SHADOW CIRCLE 4302

    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

    95

    Estimated median home price

    $525,000
    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 - 200K8
    $200K - 300K24
    $300K - 400K11
    $400K - 500K4
    $500K - 600K8
    $600K - 700K10
    $700K - 800K6
    $800K - 900K3
    $900K - 1M5
    $1M - Max16

    Homes for Sale by Type in Maitland, FL

    Property TypeCount
    Single Family40
    Townhouse5
    Condo42
    Commercial1
    Rental28
    Lots and Land5
    Condo/Town/CoOp0
    CoOp0
    Multi Family2
    Mobile Home0
    Farms0

    (Data as of 1/22/2026)

    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 1/24/2026.