There is a need for a shift towards circular economy in the construction sector and design philosophies as Design for Deconstruction and Reuse (DfDR) and Design for Adaptability (DfA) are being developed as means to design out waste and enhance resource efficiency. However, applying these philosophies is not yet common practice. The amount of DfDR/A timber buildings described in literature is limited. This study aims at increasing and spreading knowledge on DfDR/A for timber buildings. It has four goals: 1) To suggest methods to apply DfDR/A. 2) To suggest new design solutions. 3) To collect experiences on connections in relation to DfDR. 4) To suggest how guidelines for deconstruction and reuse can be formulated. The study presents three methods that all proved valuable in applying DfDR/A: one discussion-based method to improve an already existing timber building design, one indicator system to assess the DfDR/A potential of building designs, and one matrix to guide design decisions. We used the first method to conduct five case studies in four European countries. The studied designs were judged to be well or relatively well adapted for deconstruction and reuse already today. The fact that the studied buildings are all offsite manufactured and of modular composition benefits the deconstruction process, partly because construction and deconstruction are similar processes so that the knowledge and infrastructure that companies have can be directly transferred to enable deconstruction and reuse. Where large modules can be recovered, the time and energy needed for deconstruction as well as the risk for damage will be reduced. Disadvantages to deconstruction and reuse identified were typically linked to the complexity of building modules and that individual components are not independent. This was reflected as irreversible or hidden connections, inaccessible services, interconnected layers of the structural modules and many different component sizes. One of the case study buildings, designed with mass timber panels, excelled in the simplicity and reduction of number of steps required for maximum material recovery. New designs suggested included making fasteners more accessible to deconstruction, avoiding letting sensitive materials as plastic foils and particle boards pass continuously over joints between elements, and (for cases where standard units are not already used) standardizing elements. One case suggested using solid wood components instead of engineered wood products to achieve durability. The study showed that simple changes in design can lead to an augmented reuse potential. Some of the new design solutions generated will be taken into production by the participating manufacturers. Insights on connections included recognizing the fact that the use of reversible screwed connections is not sufficient to ensure deconstructability and that although nailed or glued connections severely complicate reuse of components, they might be accepted within elements in case reuse on element level is the target. Guidelines for deconstruction and reuse were developed in all case studies. Taken as a group of studies, there are advantageous additions proposed to earlier guidance documents. Despite being based on the same source, the different plans suggested varied substantially. There was a noteworthy difference between manufacturers’ in-house plans to those proposed by architects, engineers, or researchers, which speaks to the uncertainty regarding the appropriate structure and format.