wˈɪntʃkuːm bɪkˌeɪm ɐ wˈɛlθi lˈændoʊnɚ, spˈɛndɪŋ ˌoʊvɚ pˈaʊnd fˈoːɹ,zˈiəɹoʊzˈiəɹoʊ zˈiəɹoʊ ɔnðə pˈɜːtʃɪs ʌv pɹˈɑːpɚɾi ɪnðə wˈʌn θˈaʊzənd fˈaɪvhˈʌndɹɪd fˈoːɹɾi z, ɪŋklˈuːdɪŋ ðə mˈænɚz ʌv θˈætʃæm ænd bˈʌkəlbˌɛɹi ɪn wˈʌn θˈaʊzənd fˈaɪvhˈʌndɹɪd fˈoːɹɾi, fˈɑːɹnbəɹˌoʊ ɔnðə bˈɜːkʃɚ dˈaʊnz ɪn wˈʌn θˈaʊzənd fˈaɪvhˈʌndɹɪd fˈoːɹɾi tˈuː, ænd lˈɑːkɪndʒ ænd dʒˈɪndʒ ɪn wˈʌn θˈaʊzənd fˈaɪvhˈʌndɹɪd fˈoːɹɾi sˈɪks.
Winchcombe became a wealthy landowner, spending over £4,000 on the purchase of property in the 1540s, including the manors of Thatcham and Bucklebury in 1540, Farnborough (on the Berkshire Downs) in 1542, and Lockinge and Ginge in 1546.