What are the types of these 3 single-engine aircraft and one Multi engine aircraft?
The upper left one looks like a Fairchild PT-19-family monoplane trainer. Production on these started in 1939 and served through the end of the war as a basic trainer. Yours might just be the PT-19B variant, which has a hood over the front cockpit and was used for instrument training:


The upper right one looks like a Vultee BT-13 or BT-15 "Valiant" basic trainer, which were used as Air Force and Navy basic trainers from 1940 to 1944:


The lower left is actually a twin-engine plane, not a single, looks like a variant of the Beechcraft Model 18, or "Twin Beech". These were built beginning around 1937 and continued well into the Vietnam years. Military designations include the C-45 Expeditor, AT-7 Navigator, and AT-11 Kansan, but your specific example appears to be civilian:


The lower right is a North American T-6 or AT-6 Texan. Production on these began in 1933 and they were only retired from all air forces in 1996 (though the last operator, South Africa, only kept them as basic trainers because a military embargo related to its Apartheid policy prevented them buying anything newer):


As far as exact build dates of these aircraft, you might be able to look up the tail numbers of each airplane, but these craft were so common and so varied during their production that exactly when a specific airframe was built is difficult to determine by looking at it. All of these aircraft, in addition, seem to have been "civilianized" after service with the USAAC/USAAF, so their full history may be very hard to trace without their logbooks.