The article presents the comprehensive approach to planning of the new, sustainably-designed housing estate Ilovica in southern Ljubljana. It was executed as an ideal model of a larger densely populated settlement, which would also ensure the reconstruction of the extant area of low-density housing with deficient utilities provision. Besides the architectural and urbanistic design and solutions to technological problems, we also showed implementation possibilities that use instruments of real estate polices (re-parcelling etc.) and prepared a feasibility study of the investment. Such multi-faceted projects demand multi-disciplinary approaches, whereby only the full participation of various experts and also wider community can lead to better results with synergetic effects that are the result of common endeavour.