View 1988 Kenaston ROAD Maitland, FL MLS# O6189398
$425,000
3

Beds

3.1

Baths

2,103

Sq.Ft.

1988 Kenaston ROAD

Maitland, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 380 BANYAN DRIVE Maitland, FL MLS# O6338606
  • Virtual Tour
1 of 38
$429,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

380 BANYAN DRIVE

Maitland, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 1100 S ORLANDO AVENUE 208 Maitland, FL MLS# O6349155
$450,000
2

Beds

2.0

Baths

1,248

Sq.Ft.

1100 S ORLANDO AVENUE 208

Maitland, FL

Courtesy of SHORESTONE PROPERTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 736 FOREST GLEN COURT Maitland, FL MLS# O6332033
  • Virtual Tour
1 of 36
OPEN HOUSE: Saturday 1/10 11:00 AM - 1:00 PM
$479,899
4

Beds

2.0

Baths

1,647

Sq.Ft.

736 FOREST GLEN COURT

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2350 Carolton ROAD Maitland, FL MLS# O6183905
$494,500
4

Beds

2.0

Baths

1,871

Sq.Ft.

2350 Carolton ROAD

Maitland, FL

Courtesy of EXP REALTY LLC
View 1220 WINSTON ROAD Maitland, FL MLS# O6369769
  • Virtual Tour
1 of 29
$499,000
4

Beds

2.0

Baths

1,724

Sq.Ft.

1220 WINSTON ROAD

Maitland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2065 DERBYSHIRE ROAD Maitland, FL MLS# S5140785
  • Recently Listed with Virtual Tour
1 of 27
OPEN HOUSE: Saturday 1/10 11:00 AM - 1:00 PM
$499,990
3

Beds

2.0

Baths

1,430

Sq.Ft.

2065 DERBYSHIRE ROAD

Maitland, FL

Courtesy of EXP REALTY LLC
View 1231 GLASTONBERRY ROAD Maitland, FL MLS# O6364492
  • Virtual Tour
1 of 18
$525,000
3

Beds

2.0

Baths

1,753

Sq.Ft.

1231 GLASTONBERRY ROAD

Maitland, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1231 SIDCUP ROAD Maitland, FL MLS# TB8414987
  • Virtual Tour
1 of 39
OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
$535,000
3

Beds

2.0

Baths

1,798

Sq.Ft.

1231 SIDCUP ROAD

Maitland, FL

Courtesy of KELLER WILLIAMS TAMPA CENTRAL
View 2632 DERBYSHIRE ROAD Maitland, FL MLS# O6349951
$545,000
4

Beds

2.0

Baths

1,770

Sq.Ft.

2632 DERBYSHIRE ROAD

Maitland, FL

Courtesy of EXP REALTY LLC
View 135 ROOSEVELT PLACE Maitland, FL MLS# S5134555
  • Virtual Tour
1 of 47
$564,900
4

Beds

2.0

Baths

2,426

Sq.Ft.

135 ROOSEVELT PLACE

Maitland, FL

Courtesy of LA ROSA REALTY LLC
View 1470 WINSTON ROAD Maitland, FL MLS# V4945137
  • Virtual Tour
1 of 74
OPEN HOUSE: Sunday 1/11 11:00 AM - 1:00 PM
$569,000
4

Beds

2.0

Baths

2,000

Sq.Ft.

1470 WINSTON ROAD

Maitland, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 2318 CASTLEWOOD ROAD Maitland, FL MLS# O6330873
  • Virtual Tour
1 of 46
$580,000
4

Beds

3.0

Baths

2,335

Sq.Ft.

2318 CASTLEWOOD ROAD

Maitland, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 2666 DERBYSHIRE ROAD Maitland, FL MLS# O6348986
  • Virtual Tour
1 of 34
$585,000
3

Beds

2.0

Baths

1,887

Sq.Ft.

2666 DERBYSHIRE ROAD

Maitland, FL

Courtesy of RE/MAX CENTRAL REALTY
View 2453 WORTHINGTON ROAD Maitland, FL MLS# TB8454086
  • Virtual Tour
1 of 22
OPEN HOUSE: Saturday 1/10 11:00 AM - 2:00 PM
$600,000
4

Beds

2.0

Baths

1,959

Sq.Ft.

2453 WORTHINGTON ROAD

Maitland, FL

Courtesy of REALTY OF RIVERVIEW LLC
View 360 LAKE SEMINARY CIRCLE Maitland, FL MLS# O6362152
  • New Construction
1 of 5
$4,999,000
5

Beds

6.2

Baths

6,466

Sq.Ft.

360 LAKE SEMINARY CIRCLE

Maitland, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY

About Maitland

Listings in Maitland, FL

37

Estimated median home price

$400,000
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 4
$300K - 400K 6
$400K - 500K 9
$500K - 600K 8
$600K - 700K 0
$700K - 800K 0
$800K - 900K 0
$900K - 1M 0
$1M - Max 1

Homes for Sale by Type in Maitland, FL

Property Type Count
Single Family 20
Townhouse 1
Condo 13
Commercial 0
Rental 10
Lots and Land 1
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 1/8/2026)

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 1/9/2026.